Money 20/20 is built for scale. An expo floor the size of a small town, back-to-back meetings, and booth conversations that all tend to blur together. So on Monday night in Las Vegas, CMO Uncovered went the other way. We booked a long table at BOA Steakhouse and sat down with 14 growth and marketing leaders.

The conversation bounced to various places but one conversation that was worth highlighting; when you can only make the next hire, which one do you make?

Should you hire a growth person? A general marketer? Or skip marketing for now and bring on a product person to drive a product-led growth (PLG) motion?

The question sounds tactical but it’s closer to strategy. Each answer implies a theory of how the company wins customers, and every early hire builds a team in its own image. Get it wrong and you spend a year optimizing a funnel that was never the constraint, or staffing a sales org for a product that should have been selling itself.

Let the product tell you who to hire

Mrinal Parekh, Clevertap marketing lead, had an answer that reframed the whole debate. Start with what the product can and cannot do on its own.

“If your product sells itself, your PLG motion is working, so maybe you need a growth person to handle it,” he said. “When your product isn’t selling itself is when you need a sales team. And when your sales team needs support and scale, that’s when you need a marketing team.”

Unpacked, it becomes a sequence where each hire is triggered by a bottleneck:

1. The product sells itself → hire growth. Users find it, activate and pay without talking to anyone. The job is to amplify a loop that already works - onboarding, activation, referrals, retention, pricing. A sales team here mostly adds cost to a motion that doesn’t need it.

2. The product can’t sell itself → hire sales. Long consideration cycles, multiple stakeholders, a price point that demands a conversation. Someone has to carry the deal across the line.

3. Sales can’t do it alone → hire marketing. Reps are prospecting cold, pipeline is thin, and buyers haven’t heard of you before the first call. Marketing’s job is to make every sales conversation easier - awareness, demand, and a brand that gets the meeting taken.

The notable move is where marketing lands. It isn’t the default first hire. It earns its seat when the motion in front of it starts to strain.

Two caveats are worth adding. First, a company can sit in different stages at once - self-serve for small teams, sales-led for enterprise. Second, the answer moves. The hire that was right at seed can be wrong at Series B, so the diagnosis is worth rerunning every planning cycle.

Mrinal added a point that applies once marketing is in the mix. Channels shouldn’t be ranked against each other in the abstract. “You can’t pit digital versus events,” he said. “They both have their own place.” A paid campaign captures demand that already exists.

Diagnose first, then hire

The question brought to the table is one nearly every growing company faces, usually with less time to think about it than it deserves. The answer that emerged over dinner is disciplined in its simplicity. Find where customers actually get stuck, and hire the person whose job is to unstick them.

This was one of several threads worth pulling from that night at BOA. In part two, we’ll pick up another - how marketing leaders are creating protocol on internal AI-written work as 2027 planning gets underway.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

Ryan Hartman once managed a $100 million digital advertising budget at GEICO. So when we asked how he was deploying marketing dollars at Chaiz, the extended car warranty marketplace he co-founded, we expected to hear about the channels and experiments producing his best customers.

He smiled.

Chaiz had tested paid media, he explained, but its growth was coming largely through organic discovery and partnerships. At the time of our conversation, Ryan said customer acquisition costs were the lowest they had been. The marketer who had spent much of his career buying attention was spending more of his time finding businesses that could distribute his product.

That shift became more interesting as we understood what Chaiz had decided to give up. Customers could compare warranty prices without entering an email address or phone number. They could research coverage without agreeing to a conversation with a salesperson. For a company trying to grow, those decisions meant fewer prospects to follow up with.

For a company selling extended car warranties, Ryan believed they were necessary.

Before Chaiz could persuade someone to buy, it had to address what they expected would happen if they expressed interest.

Ryan had encountered the need for the product himself. After roles at GEICO, Esurance and Custom Ink, he joined insurance comparison marketplace The Zebra, where he watched the company grow from roughly 20 people to more than 400. He was considering his next move when his car needed an engine repair that would cost about $10,000.

The mechanic hoped he had an extended warranty. He didn’t.

Researching the market, Ryan saw a familiar pattern — a complicated financial purchase that consumers could benefit from an online comparison. But the sales process carried its own baggage. Dealership pressure, unsolicited calls and opaque pricing had shaped how people thought about the category.

Chaiz built a marketplace where customers could compare plans from multiple providers and purchase online. The providers underwrite the coverage and handle claims. Chaiz’s job is to help customers choose among them.

That distinction also creates a responsibility. Ryan said the company has turned away prospective providers after reviewing their reputations and finding concerns about unpaid claims. Every provider admitted to the marketplace becomes part of the experience on which Chaiz’s own reputation depends.

The same thinking shaped its quote process. Asking for contact information before revealing a price might create a useful lead for a sales team. It also asks the customer to accept an uncertain consequence just to learn what something costs.

The commercial cost is real. Without an email address, Chaiz has fewer opportunities to bring an undecided shopper back. We wanted to understand how Ryan reconciled that choice with the work of building a customer base.

His answer started with an unfamiliar search query.

People were searching for “warranty by VIN,” and the team wanted to know what they meant. These drivers were trying to determine whether their existing factory warranty was still valid. They knew their car’s age and mileage but couldn’t necessarily remember the coverage limits.

The question came before a purchase decision; Do I already have the protection I’m looking for?

At a company off-site, Ryan worked with an engineer and a designer to build a tool that could answer it. He said they brought it to market about a week after developing the idea.

The tool does collect an email address. In return, the driver can check their factory warranty status. If coverage has expired, Chaiz can offer extended warranty options. If it remains active, the company has information it can use to follow up closer to expiration.

That was the detail we kept coming back to. The team had found a reason to collect information that followed directly from the customer’s question. Someone comparing prices could continue without surrendering their contact details. Someone checking existing coverage could receive a message tied to when that coverage would end.

For a marketer, those are very different relationships. One begins with a person’s willingness to enter a funnel. The other begins with a specific problem the company has helped them understand.

Ryan’s approach to distribution follows a similar logic. He spends much of his time developing partnerships with companies that already have a relevant relationship with the customer. Chaiz has built APIs that let partners incorporate its warranty offering into their own websites and purchase experiences. Ryan described working with peer-to-peer car marketplaces and financial businesses, including NerdWallet and Self Financial.

Car insurance offers a particularly clear connection. A customer has just arranged protection against an accident. Mechanical breakdowns remain a separate expense. Introducing warranty coverage at that moment gives the product a context the customer already understands.

Building those relationships requires technical work alongside marketing. A prospective partner needs a straightforward way to present the plans and move a customer through checkout. Chaiz’s integration becomes part of its ability to win distribution.

His experience in paid media hasn’t stopped being useful. It has helped him judge where a small company’s resources can go furthest. At Chaiz, that has meant concentrating on specific search opportunities and making the product easier for established businesses to offer.

There are limits to what we can conclude from that strategy. Ryan’s account of lower acquisition costs doesn’t tell us how much each decision contributed, or how the mix will change as the company grows. Forgoing contact details also leaves Chaiz with a constraint its competitors may be happy to avoid.

But the warranty-by-VIN tool shows how the team is working within that constraint. A search query revealed uncertainty. Marketing, design and engineering built something to resolve it. The result gave Chaiz both a useful service and a more relevant opportunity to follow up.

A driver whose factory warranty is still active may have little reason to purchase today. Chaiz can answer their question anyway. When that coverage approaches its end, the company has something specific to say.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

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In 2024, 77 million Americans belonged to a gym. That’s one in four people. Memberships are up 20% since 2019. Demand isn’t the issue, keeping people is. The average club only keeps about 66% of its members year over year.

Much like fashion, fitness fads come and go. In 2022, SoulCycle closed 20 of its 83 studios, and we all watched Peloton stock fall 90% from its late-2020s pandemic peak. The Zumba story is different. Popularity spread through gyms and instructors, shielding the brand from the boom and bust cycle experienced by brands like SoulCycle, CrossFit, Orangetheory, and Peloton.

Zumba started in 2001, and by 2002 the company was selling DVDs via late night infomercials. After experiencing moderate success from DVD sales, they decided to launch Zumba Academy for instructors and a $40-monthly instructor network. Today, roughly 15 million people take a class each week throughout 200,000 locations across 189 countries.

We sat down with Zumba CMO, Carolina Moraes to discuss what it’s like to sit at the growth helm of a 25 year old brand built by the people. She has been with the company for 14 years, and her challenge has never been brand recognition, it’s getting people to fully understand the product.

Influencers Before They Had a Name

Zumba never invested in acquisition marketing. Instructors did all the work, posting classes and bringing in students. They felt the brand was as much theirs as it was the company’s. This built massive awareness and following but with a catch. Many students associated Zumba with the instructors and didn’t realize it was a brand. With no physical locations of its own, the company can’t fully control the class experience.

However, gym partnerships have filled this gap. Gyms hire only certified instructors, checking numbers in a shared database. When a talented teacher shows up uncertified, the gym often sends them to get trained, which has become a pipeline for new instructors.

Zumba can’t script every influencer or celebrity that talks about it, so they intentionally keep the positioning wide: Inclusivity, every size and shape, no right or wrong as long as you’re moving. When someone asks about being off messaging, Carolina asks, “are they moving? If so, the brand is doing its job.”

Brand Briefing With Community First

They have a dedicated team listening to the community. This is a different operation from customer care, because people who advocate for a brand need different attention than buyers.

Before any campaign goes to the creative team, the brief lays out how Zumba wants the community to feel, what it hopes they’ll say, and which points should be avoided.

Music Earworms You Have to Attend Class to Hear

Zumba began with a forgotten cassette. When co-founder Beto Perez misplaced his usual music for an aerobics class in Colombia, he had to pop in his salsa and merengue tapes instead, and the result is Zumba.

Music can make or break a workout, and it’s a big reason Zumba stays a top class in most gyms. New music and choreography launches every other month. Roughly 70% of the songs are made for Zumba with outside artists and labels. The other 30% are licensed radio hits, mixing the familiar with the new. Owning the sound makes Zumba hard to copy.

In one month, a class might move from Rio funk to Bollywood to belly dance. Carolina recently returned from Seoul where she shot a K-pop volume. Asked why Zumba is still a top class, Carolina says, “We’ve traveled with the musical trends.”

Twenty five years in, Zumba is still growing by staying close to the people. In the full interview, Carolina explains how Zumba reinvented itself when COVID shut down every gym, and how the company sets new instructors up for success in their first three months. Listen to the full conversation to hear how she balances brand control with community ownership.

In 2004, the U.S. homeownership rate averaged 69%. By 2025, it was 65.2%. During the first quarter of 2025, 46.1 million American households rented their homes, and nearly half spent more than 30% of their income on rent and utilities. Making the idea of homeownership feel unobtainable.

The founders of Bilt saw this pressure amongst their own friend circles, and decided to build a company centered on essential expenses, because the milestones their parents had reached were becoming increasingly harder for their generation to afford.

Bilt emerged to let people earn rewards on the rent they are already paying. Points could go towards travel or a future downpayment, giving members something back from an expense that typically offered little beyond a roof over their head.

For Zoe Oz, Bilt’s CMO, the marketing challenge began with education. This was something completely new. People understand airline miles and credit card points but rewards on housing required some explaining.

Traditional advertising would not build the company they envisioned. Instead, Bilt developed relationships with property owners and managers to be integrated in how people pay for housing, placing the company inside an existing habit.

Once members enter the Bilt ecosystem, the next challenge is figuring out what the renter will need next.

Signing Up Comes Before Understanding

Most businesses struggle to establish enough value to get a customer, Bilt acquired customers to make a rent payment.

However, residents might use Bilt every month without understanding much about the actual membership. They know where to go to pay rent but have no idea Bilt offers benefits like at restaurants or fitness studios.

When someone first moves into a new place there are immediate concerns: payments, maintenance, or package delivery. Messaging about pharmacy rewards will be useful eventually but probably not right away. That changes strategy for lifecycle marketing. Bilt has to decide which benefit is worth introducing when people are actually ready to use them.

Making the First of the Month Hit Different

Around the first of the month, customers opened the app to pay rent and check their email to make sure the rent went through. This is a dependable point of contact which was also attached to dread.

Rent Day was born from that observation. Bilt introduces bonuses, experiences, special releases - including A$AP Rocky vinyl - to make the first feel special instead of dreadful.

Bilt has larger ambitions around neighborhood partnerships. Zoe describes restaurant checks that come with a complimentary Lyft ride home. The value grows when it helps members do something they already want to do.

The monthly rent payment gives Bilt a recurring place but what happens beyond that payment determines how far the relationship will go.

A CMO spends a surprising amount of time explaining marketing. Why brand matters. Why growth is not a button. Why customers notice everything. Why the campaign cannot be faster, cheaper, more measurable and somehow also iconic.

There’s also an enormous amount of opinion coming from all corners of the company. The CMO’s job is to absorb all of this input and still produce a coherent idea on the other side.

Which is why there is a particular relief in sitting down with people who already understand the assignment.

In August, CMO Uncovered brought 15 marketing leaders together at Kappo Kappo in Austin. There was no panel or presentation. Just one table filled with people who get it.

In a room curated for CMO’s, no one has to spend the first 20 minutes establishing things like that brand and revenue are related. Or that customers are human beings. Or that the most measurable idea isn’t automatically the most meaningful. They get to speak candidly about their greatest challenge or marketing unlock.

CMOs sit at a complicated intersection in most companies. They are close enough to the customer to notice when something is changing, but they still have to convince the organization to move. They are asked to protect what makes a brand recognizable while continuously reinventing it. They must know what people want now and have an opinion about what they will want next. That’s a tough gig.

Peers help each other see the difference between a problem unique to one company and a shift happening everywhere. They offer context, contradiction and, occasionally, the reassuring discovery that someone else is also trying to solve the impossible thing. That was the vibe of CMO Uncovered After Hours.

CMO Uncovered exists because marketing is often the loudest team in the company, while the thinking behind it receives far less attention. We create spaces where marketing leaders can talk with people who understand the work, whether the conversations turns to growth or a collection of beer steins. Getting to know the person behind the title is part of the point.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

A franchise can make a character famous but fans decide which moments become theirs. Youtooz pays close attention to the expressions, gestures and moments that audiences cling to and turn into shorthand. It gives those moments something physical to collect that sparks an immediate connection between people who know exactly why this detail matters.

The company releases nearly 200 products every month, and co-founder Mark Prokoudine is candid about how often the company misreads how big or small a fandom might be. “Our predictions on what product might do well are all over the place - we’re wrong all the time - so experimentation and trying new things is a big part of our company culture”

Online attention is abundant and highly visible, but it doesn’t necessarily reveal how much people actually care. A creator can attract millions of followers without building a community that wants to own something connected to them. Mark found the sweet spot, an obscure reference that generates far more demand because a smaller group recognizes exactly what it means.

Youtooz has worked inside that gap since 2019, when it began turning the internet’s shared references into physical collectibles. Its first release sold out in eight minutes, and the company produced roughly 70 creator figures that year. Its first licensed property was the clenched fist from Arthur, a split-second reaction that the internet had transformed into a universal expression of barely contained frustration. People saw the image, understood the feeling and recognized everyone else who was in on the joke. Youtooz had found the small, specific moments that make a sprawling internet culture feel like a community.

Audience size isn’t the entire picture

When Youtooz evaluates a creator, Mark looks past the most visible measure of influence. “How deep does the fandom go?” he asks.

Follower count can show how many people a creator reaches. It says less about whether those people share references, recognize recurring characters or want an object that signals their connection to the community. Youtooz looks for the behavior beneath the number. Paying close attention to the jokes repeated and the details noticed about characters, is what determines fandom success.

That approach leaves room for products that would look small through a conventional reach calculation. Ectoplasm Randy, a specific South Park reference, became one of Youtooz’s strongest social releases. Some of the best social media days in the company’s history came from tweets about the figure.

The response did not come from choosing the most prominent character or the broadest possible idea. It came from recognizing a detail that carried unusual weight for people who understood it. Those fans did not need an explanation of why the figure existed. Recognition was the appeal.

That difference becomes especially useful in creator marketing, where brands often treat audience size as a proxy for commercial value. Youtooz needs more than distribution from a partnership. The creator or property must have enough cultural material to support a product people will display, share and place alongside other objects that represent who they are.

Content that behaves like fandom

Youtooz applies the same thinking to its own social strategy. Some of the company’s most successful videos resemble fan-made arts-and-crafts projects more than conventional product advertisements.

One of its most viewed TikToks was a live creation of a handmade world for the adorable SpongeBob cockroach. I’ve personally watched the video at least 20 times, so I get the virality. The videos use the product, but the figure doesn’t carry the entire piece of content. The team returns to the source material, finds a detail fans already enjoy and gives them another way to participate in it. It’s genius.

That approach has helped Youtooz generate roughly 100 million organic impressions each month across TikTok and Twitter. The scale comes from producing content people will engage with even when they are not ready to make a purchase. Fans can recognize the joke, debate the interpretation or share the video with someone who knows the same reference.

The products also circulate without Youtooz directing every appearance. Jack Harlow unexpectedly placed a Youtooz figure in a music video, introducing it in a setting the company did not create or buy. The placement worked because the figure could function as part of the culture around the artist rather than as an interruption to it.

For Youtooz, community and content are connected. The team watches what fans respond to, then creates more material from the worlds they already care about. Social media supplies reach, but the quality of the response helps reveal whether that reach contains a market.

The website turns attention into evidence

Social engagement reveals recognition, and the website proves whether that recognition becomes a purchase.

Every product is launched direct-to-consumer as a preorder. When Jimothy the raccoon became an internet meme, Youtooz moved from an initial concept to a product ready for preorder in roughly two weeks. The listing went live while the reference was still circulating, allowing customers to respond before the team had to guess how long the attention would last.

That pace depends on an in-house art operation in North America and its own office in China, bringing design and production into a structure built for high frequency releases. Marketing can identify an opportunity, but the rest of the organization must be able to act while the cultural reference is still current.

The preorder connects those functions. It turns an interpretation of internet culture into an offer customers can accept or reject. At nearly 200 launches a month, Youtooz receives a steady stream of confirmation about the difference between what people enjoy online and what they will pay to own.

Mark still considers the company’s website its largest source of growth, even as Youtooz expands through Spencer’s, Hot Topic and Target. Retail gives the brand greater distribution, but it remains additive to the direct channel. Youtooz can introduce a highly specific product to its existing community online, learn from the response and then extend its reach through stores.

TikTok Shop shortens that path further. Mark sees the platform, along with affiliates, live shopping and user-generated content, as an important opportunity for direct-to-consumer brands. A fan can encounter a reference, see the product and purchase it without leaving the platform where the interest began. The content and the transaction no longer have to live in separate parts of the customer journey.

Unpredicted success of a viral moment

Youtooz’s relationship with Wall Street Bets shows how difficult it can be to know where a cultural reference will lead. During the GameStop trading frenzy, the company collaborated with the community on several products, including a figure based on the “stonks” meme.

The opportunity began with an active group that had developed its own characters, language and visual shorthand. Youtooz could see that people understood the joke and identified with the community around it. That was enough to justify making the collectible.

The attention surrounding GameStop eventually receded, but “stonks” continued to travel. Youtooz later acquired the intellectual property and began receiving royalty payments when documentary studios used the image to explain the era. A meme that began as material for a product had become an asset that other companies licensed to tell the story of the event. Youtooz could not have predicted that second life.

Youtooz has built its business by staying close enough to fans to see which references they want brought to life, giving those references momentum through content, and testing demand through preorders while the connection is still strong. For most CMOs, recognizing a cultural moment is just the beginning. The harder work is building an organization that can move as quickly as its audience decides something matters.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

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The market around Scribd, Inc. is not as tidy as “documents.” It sits inside a much larger fight over how people learn, research and decide what to trust online. The global e-learning services market is projected to grow from $426 billion in 2026 to more than $1.7 trillion by 2034. Digital publishing is expected to reach nearly $280 billion over the same period. Add AI answer engines, search, study tools and workplace research platforms, and the real category becomes harder to name but easier to understand.

For years, Scribd had the kind of user intent most brands spend fortunes trying to manufacture. People arrived with a need already in hand. They were looking for a manual, a source, a study aid or a document they could not easily find somewhere else. They searched, landed on Scribd, found what they needed and moved on.

The company occupied a valuable position in the search-led web, where a user might end up after asking a specific question, when an answer still required a source and the source still required reading.

Nearly twenty years later, that world has changed. Search is no longer a simple doorway between curiosity and destination. A person may ask a question and never leave the results page. A summary may appear before the source. An AI agent may decide which information is worth recommending before the user ever sees the options.

That brings us to Scribd CMO, Gemma Craven, and their first major brand campaign, “Connect the Docs.” The campaign is aimed at students and educators, but the question underneath is larger than education. What happens when getting an answer becomes easier than understanding one?

That is what makes Scribd’s moment interesting. The company is trying to move from a utility people find by accident to a brand people choose on purpose, while attaching feeling to a behavior that has become almost unfashionable in the age of instant answers.

This is the question growth leaders now have to answer. When discovery is shaped by search summaries, AI agents, reviews, Reddit threads and every public trace a company leaves behind, how much of the brand still belongs to the brand?

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• Search did the selling: For years, Scribd didn’t need brand love. People Googled what they needed, landed on Scribd and moved on.

• The AI plot twist: Instead of making Scribd obsolete, quick answers sent more people looking for source material, verification and depth.

• From library to workspace: Gemma says Scribd is moving from a passive library to a knowledge workspace where people find, learn and finish the thing.

• Your next customer may be a machine: Brands now have human audiences and machine audiences. An AI agent may decide if you matter before a person ever clicks.

• Reputation is the new homepage: Reddit threads, app store reviews, customer service, YouTube, press and Wikipedia all shape what the internet thinks you are.

• Thinking is worth saving: Scribd’s first major brand campaign is built around the joy of figuring something out yourself. A little radical in the age of instant answers.

Listen to the full podcast here.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

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Brand collabs have become marketing’s favorite shortcut to attention. Combine two recognizable names, create scarcity and hope the internet responds.

The best collabs don’t create chemistry, they reveal it.

Which brings us to Will Ferrell in his underwear.

We’ve all seen this man half-dressed more times than we can count, whether it’s Talladega Nights after the fiery car crash or Old School when he goes full Frank the Tank. At this point, Will Ferrell in briefs is basically part of the American visual canon, so when SKIMS put him on a golf course in pale blue briefs, knee-high socks and a visor, the joke didn’t need explaining.

Ferrell was playing Lonnie “The Hawk” Hawkins, the aging pro golfer at the center of his Netflix comedy series, while Kim Kardashian delivered the line, “His body says retire. His SKIMS say one more round.”

It’s surprising for about three seconds, and then it feels as though someone should’ve brought us this years ago.

SKIMS didn’t have to invent some elaborate reason for Ferrell to be there. Audiences already associate him with a particular kind of half-naked absurdity, and the brand simply stepped into the joke. That’s what the strongest pairings tend to do. They don’t force two audiences together and hope a connection appears. They notice the connection first.

Two brands walk into a Target

On the surface, e.l.f. Cosmetics and Liquid Death touch very different markets and have no overlap. One sells makeup. The other makes canned water as if it were contraband from a metal festival.

But, in 2024, they launched Corpse Paint.

The $34 limited-edition makeup kit came packaged in a coffin and included black lipstick, white eyeshadow, dark eyeliner, setting spray and a makeup brush. Basically everything you’d need if KISS suddenly lost a band member.

It sold out in 45 minutes, and 68% of the buyers were new to e.l.f.

That 68% figure is powerful for the case study, but the coffin is why people cared. Neither brand behaves the way its category is supposed to. e.l.f. doesn’t treat beauty like a sacred ritual, and Liquid Death has spent years building an elaborate joke around the idea that drinking water should feel faintly dangerous. A coffin full of makeup was not a stretch for either of them.

They live in different Target aisles, but their customers would probably find each other at a party and talk for hours.

Whole Foods and Fishwife are playing a different version of the same game.

Their one-can sardine tote is opulent, and it’s also painfully accurate for a certain person. She has opinions about olive oil, probably owns linen napkins and has absolutely found a place for canned fish on her charcuterie board.

The tote works because it understands the buyer well enough to tease her. It’s less a piece of merchandise than a personality test with handles.

Demographics miss the fun stuff

Marketers can describe a customer with uncanny specificity.

Women, 25 to 34. Household income above $100,000. College educated. Urban. Married.

That’s useful when you’re buying media, but it tells you almost nothing about whether someone will buy a coffin-shaped makeup kit or send a friend a photo of a sardine tote with, “I need this.”

The useful information is often softer and messier. Taste, humor, references and the brands people choose all say something about how they see themselves.

On an audience spreadsheet, e.l.f. and Liquid Death look unrelated. Put the products next to each other and somehow nobody needs an explanation. The overlap has less to do with category than with worldview.

SKIMS and Will Ferrell share a joke. e.l.f. and Liquid Death share an appetite for absurdity. Whole Foods and Fishwife know exactly which person thinks one overpriced tin of fish deserves its own carrying case.

That’s considerably more useful than saying two brands have “audience overlap,” and it’s also why the current obsession with unexpected pairings can go sideways so quickly.

You can make almost anything look interesting for 24 hours. Put a luxury logo on Crocs. Turn a snack food into a sneaker. Package an ordinary object like a museum piece and call it limited edition.

You’ll get screenshots.

What’s harder is making the pairing mean something after launch day.

The best ones tend to produce two reactions in sequence. First, What? Then, almost immediately, Oh, of course.

You can manufacture the first reaction. The second depends on understanding what people actually think your brand is, which isn’t always the same thing your positioning deck says it is.

But cultural fit is only one way to find the right partner, and there’s another route that may be even more useful because it doesn’t depend on taste alone.

Look at what your customers are already doing.

Sometimes the partnership is already happening

Dropbox didn’t have to invent its relationship with Fred again.. His team was already using the product.

During his USB002 tour, Fred asked fans to put away their phones and actually watch the concert instead of spending two hours collecting blurry footage they’d probably never look at again. His team captured the good photos and video, then put everything in a Dropbox folder for fans afterward.

You got the memories without becoming the unpaid videographer for row 105.

When we spoke with Liz Armistead, vice president of brand at Dropbox, she told us the company gets plenty of inbound interest from creators who already use the product.

It’s the kind of thing that sounds obvious only after somebody points it out. Marketing teams can spend weeks building dream lists of famous people while someone genuinely interesting is already using the product every day.

Fred again.. wasn’t valuable to Dropbox simply because he had an audience. His team had already found a way to make Dropbox part of the concert experience, so the campaign didn’t need to invent a use case or manufacture credibility. The behavior came first.

That changes where marketers should look.

Maybe there’s a creator using your product every night on tour. Maybe nurses have built a workaround nobody on the product team knew about. Maybe one customer segment opens the app three times more often than everyone else, or some unexpected industry keeps showing up in inbound sales.

Those patterns can tell you more about a potential partnership than another brainstorm about who happens to be culturally relevant right now.

A lot of partnership planning still begins with the same spreadsheet. Someone lists creators or brands, adds follower counts, audience demographics and engagement rates, and then the team debates who feels most “on brand.”

I’d start with a different list.

Who already pays you? Who uses the product obsessively? Who keeps mentioning you when there’s no contract attached? Which customer story gets passed around internally because even the company didn’t realize people were using the product that way?

Now you’re looking at behavior instead of aspiration, and when the relationship already exists, the campaign doesn’t have to spend half its time explaining itself.

Super.com found NASCAR in its own data

Super.com got to NASCAR another way, through its customer data.

The company had grown largely through performance marketing, and when the team began spending more heavily on brand, it looked at where its customers were already spending their time.

NASCAR kept showing up.

Rick Galasieski, general manager of financial products and earnings at Super.com, told us instinct can get him interested in an opportunity, but the numbers still have to agree.

Then he went to Talladega.

Rick arrived at the Super.com tent expecting to do what marketers normally do at an event. He was ready to explain the company to strangers and convince them to care.

He barely got the chance.

People started walking up, pulling out their phones and showing him they were already Super.com members.

You spend months building audience segments and analyzing affinity data, and then the customer walks up in a NASCAR T-shirt and hands you the answer.

Super.com wasn’t inserting itself into NASCAR culture and hoping it fit. Its customers were already sitting in the stands.

That matters because the internal pitch for a brand partnership is usually predictable. They have people we want, we have people they want, and together we’ll reach more of both.

Sometimes that’s exactly the right reason to do it.

But Dropbox and Super.com point to another possibility. A partnership can be less about finding a new audience than showing your existing one that you understand who they are.

Super.com at NASCAR says, we know where you spend your weekends.

Dropbox with Fred again.. says, we know how this product fits into your creative life.

Neither one requires much explaining because the customer already understands the connection.

That’s a much stronger place to begin than choosing a famous person and working backward until somebody can make the PowerPoint logic sound convincing.

Look before you brainstorm

Before building another celebrity wish list, it may be worth spending a few hours somewhere less glamorous, including customer data, social mentions, support tickets and conversations with sales.

Who keeps showing up without being paid to? Where are your best customers spending their time when they’re not interacting with you? And which customers are using the product in ways nobody anticipated when the original use cases were written?

That’s how Dropbox found a relationship that was already happening, and it’s how Super.com learned that part of its audience was spending weekends at NASCAR races.

A marketer can convince themselves that almost any celebrity is “on brand” if the deck is good enough. Actual customer behavior is harder to talk yourself around.

So maybe the simplest test for a potential partnership is whether you can explain why it works without mentioning audience size.

If the answer is that the brands share the same joke, the same taste or the same customers, there’s probably something there. If the explanation begins with follower counts, impressions or “access to a new demographic,” you may just have a media buy wearing a collab costume.

The best partnerships rarely create the connection from scratch. More often, somebody was paying enough attention to notice that it was already there.

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The baby gear industry generates roughly $356 billion annually, a number expected to reach $580 billion by 2033. And that doesn’t include diapers and formula. We’re talking about strollers, carriers, bags and all the other necessary parenting accessories.

Every irritating, painful, exhausting little moment of raising children has become opportunity for product development.

In 2018, Tushbaby launched around one of the most universal; carrying a 20-pound toddler on your hip. I spent seven years carrying three boys that way, with one hip jutting out to keep a hand free. The result was chronic wrist, shoulder and back pain. If Tushbaby existed in 2010, I would have purchased one instantly.

However, in a $356 billion industry, it’s not enough to find the problem, that’s just the start.

Parents are surrounded by product choices, and it’s difficult lift for a brand to convince a parent they need what you’re selling.

That was the challenge Sara Azadi stepped into as Tushbaby’s co-founder and CMO. The company arrived during what she describes as the Wild West of direct-to-consumer. Brands could move quickly, acquire customers cheaply and build awareness without traditional retail presence.

As the DTC playbook became more expensive and crowded, Sara’s job got more difficult.

• The death of lifecycle marketing: Consumers are increasingly turning to AI-mediated shopping, fundamentally changing how brands acquire and retain customers.

• Exhaust your copycats: If you can’t win on price, beat them with better quality, safety, brand confidence and constant product improvement.

• Listen to your fans: When your customers show you other ways they’re using your product, listen. Tushpuppy sold out in weeks of launching.

• Don’t over-build your team: Build a lean team with cross-functional understanding. Things change too quickly for narrow focused experts. 👆🏽 Case-in-point to the role of a lifecycle marketer.

• Career Advice: Build a jungle gym, not a ladder.

Enjoy the podcast and this adorable video.🐰 — Brandy Whalen, editor

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

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In 2025, Americans were charged nearly $397 billion in property taxes on single-family homes. The average annual bill reached $4,427, and that was up 3% from 2024. Property taxes remain deeply unpopular with homeowners, yet, despite the unpopularity, fewer than 5% of homeowners dispute the assessed value used to calculate their annual bill.

On Paper, Ownwell’s value proposition looks almost frictionless. The company challenges the assessment on a homeowner’s behalf and gets paid only if it saves them money.

When Chang Fu joined Ownwell as the vice president of marketing and growth, he had actually challenged and won his own assessment in Seattle. This made the case for Ownwell’s existence seem obvious, challenge an inflated assessment, lower the bill.

Then he decided to navigate the appeals process on his own in a different market — Austin, Texas. This time, he knew more and prepared himself with data and evidence. As he waited to present his case at a formal hearing, he was unexpectedly nervous. The experience exposed something his Seattle appeal hadn’t; the cost of challenging the assessment wasn’t limited to money. There was also the time, expertise and anxiety required to do it.

“I thought it was all about savings. I was wrong.”

The Burden Has a Name

What Chang experienced was given a name by public policy researchers who spent years studying what happens when people are forced to navigate complicated government systems. It’s called administrative burden.

The researchers behind the framework break administrative burden into three types: learning costs, compliance costs and psychological costs. Property tax appeals manage to hit all three.

First, a homeowner has to determine whether an assessment is actually incorrect, understand what evidence matters for their particular jurisdiction, and meet local filing deadlines. Then comes the collection of evidence. This might entail comparable sales, property records, photographs, and any other necessary information. Finally, depending on the jurisdiction and outcome, there may be negotiations or a formal hearing.

Those rules vary from one place to another, changing the way Ownwell has to think about both its product and its messaging. The obvious value proposition is a lower property tax bill, but the company also absorbs the learning, work and anxiety required to pursue one.

This is the part of Ownwell’s value Chang didn’t fully appreciate until he was sitting in his own hearing with all of his prepared evidence.

When an Offer Sounds Too Good

Ownwell’s economic proposition sounds unusually favorable for the homeowner. Let the company evaluate the property, handle the appeal, and pay only if Ownwell saves them money.

Consumers are trained to be wary of a too-good-to-be-true deal.

The offer doesn’t immediately inspire confidence. It creates questions. What information does the company need? What happens to that information? What am I agreeing to? How realistic are the savings? Why would a company do all of this work without charging upfront?

The strength of the offer ultimately became positioning friction for Chang and his team. They responded by letting the economics speak for themselves with specifics. Instead of throwing out a theoretical best-case savings scenario, they show the current assessment, applicable tax rate, the property value based on supported evidence, and the potential savings.

Additionally, if Ownwell takes a look at all the evidence and it doesn’t support a reduction, they tell the client to wait. A company can tell people that its incentives are aligned with theirs, but recommending against filing an appeal gives them proof to trust.

National Market, Administered Locally

Every homeowner in the country pays property taxes but every state and county has different regulations and rates. The economics of homeownership can look completely different in Austin, Atlanta, and Long Island.

Early in Ownwell’s expansion, the company occasionally entered markets without fully appreciating those differences. From headquarters, the marketing made sense. However, on the ground, Ownwell could look like a tech company arriving with software and data to solve a problem rooted in local government.

That can be a dangerous perception when the service depends on understanding rules homeowners find difficult to navigate. So team members began traveling to cities to speak with customers. They looked at their own billboards and marketing materials, and scrutinized which messages felt off-brand in the local market.

The company also built relationships with local organizations and recognizable figures including the San Antonio Spurs, the New York Islanders, former Texas football coach Mack Brown and Austin youth soccer organization FC Westlake. These partnerships were confirmation that Ownwell understands the markets where it operates. The partnerships help establish the local credibility Ownwell needs when asking homeowners to trust it to navigate government systems on their behalf.

“People really care that you understand their market, their situation, their specific home.”

Technology companies are usually rewarded for doing the opposite. They automate work that once required people, and reproduce successful campaigns across markets, removing local variation wherever it creates unnecessary cost.

Chang and his team understand that the homeowner’s assessment belongs to a particular house in a particular county operating under a particular set of rules. The closer Ownwell gets to reducing a homeowner’s assessment, the more those details matter. But understanding the system is only useful if Ownwell can convince homeowners to engage with it in the first place.

When Your Competitor Is Doing Nothing

For all of the complexity Ownwell removes from the tax appeal process, Chang’s biggest marketing challenge is remarkably simple. He’s competing with doing nothing.

Property taxes are unusual in that homeowners can be deeply unhappy with the assessment and still accept it. That creates an odd marketing problem for Ownwell. The company doesn’t necessarily have to persuade homeowners that property taxes are too high. Many already believer they are. It has to persuade them that the number can be challenged and outsourcing the process is worth doing.

It’s confession time. I had a chance to fight my property tax assessment, and did nothing. I’ve been following the Ownwell story since 2024. I’m intimately familiar with the value proposition and ease of engagement, and still didn’t take action.

It gets worse. I live in Denver, Colorado, and, on cue, Ownwell sent a mailer ahead of my appeal. A week later, my assessment arrived higher than ever. I remember thinking how genius the timing of the mailer was and deciding this was the year I was going to appeal. For seven days, the task was on my to-do list, then eventually fell off entirely. By the time I thought about it again, it was too late. The window had passed and I once again accepted my 140% increase.

After listening to Chang describe Ownwell’s greatest marketing challenges, I realized that he was speaking to my behavior. Every hesitation I had, Chang named. I knew there was something I could do about it. I even knew the company offering to do most of the work. And still, inertia won.

That’s the clearest example of the challenge Ownwell is aiming to solve. Sometimes the hardest part of changing behavior isn’t giving people a better option, it’s getting them to act.

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During his USB tour, Fred again.. asked fans to put away their phones. His team would document the show and send out a Dropbox folder afterward with professional photos and videos that people could save or post. The audience did not have to choose between preserving the night and being present for it.

Dropbox made the arrangement possible without demanding attention during the concert. The product appeared later, after it had already removed a small but familiar anxiety from the room.

When Fred’s team approached Dropbox after the tour, the company helped expand the idea into a broader campaign built around the content and the way his team worked. Liz Armistead, vice president of brand at Dropbox, had not created the original use case. Her team’s role was to understand why it worked, give it more reach and avoid sanding away the parts that made it feel like Fred’s idea.

That approach has become central to how Liz markets a product that often disappears inside other people’s work. Dropbox is rarely the finished film, song, campaign or design. It is where the unfinished versions move between the people making them.

Find the behavior before writing the brief

Liz has spent much of her career marketing technology that cannot be placed in someone’s hand or photographed at the center of a glossy campaign. Dropbox presents an even more specific challenge because much of its value appears before the public sees anything. Files move between collaborators. Feedback arrives. Contracts get signed. Rough versions become better versions.

The brand becomes easier to understand when Dropbox shows what customers are already doing instead of constructing an elaborate story around the software itself. Many of the company’s creator partnerships begin as inbound requests from people who use the product and want to explore what else they might do together. Liz’s team then chooses which ideas fit, shapes the program and makes sure the work reflects the product accurately.

Maison Margiela approached Dropbox with a proposal to share material from its historical folders with the public. The Dropbox team customized the folders, added visual details inspired by the fashion house and supported the release across its channels. Designers and fans could look through the work, study it and use it as material for something new.

The campaign worked because the folder was not treated as a digital display case. It became part of a continued creative exchange. Dropbox supplied the structure, but Maison Margiela determined what the community was being invited to see.

Liz has followed the same pattern on a much longer timeline at Sundance. Dropbox first attended the festival in 2015 with a hypothesis about how films were being made. Production teams handle enormous files, work across locations and rely on people who may never belong to the same company or use the same systems. The workflow seemed suited to Dropbox, but the team went first to interview filmmakers and understand what was actually happening.

They learned that 68% of Sundance films had been made using Dropbox. They also learned that many filmmakers thought of it almost entirely as storage. A crew might use Dropbox to move footage while still passing around paper release forms in the field, unaware that a signing tool lived inside the same platform.

Dropbox gradually expanded its Sundance presence around those gaps. It began by listening and educating, then added panels, premieres and programming that allowed customers to explain how they had made their work. A decade later, the company had a branded house on Main Street, but the program still grew from the same question: How are people already working, and where is the process harder than it needs to be?

Liz learned that habit at IDEO, which she considers more useful than graduate school. The work taught her to study customers in context rather than rely only on what they report in a survey. A broad sample can tell a team which idea is easiest to understand, but the easiest idea may also be the least interesting. Liz will sometimes learn more from a dozen detailed conversations, an extreme user or a parallel industry than from a large group selecting among polished options.

The most important product moment is also the most vulnerable

The Sundance research showed Liz where Dropbox sat in a creative workflow. A later campaign helped her name the emotional moment inside it.

Most creative work begins in private. A song, film, presentation or design can remain protected while its creator revises it alone. Sharing changes the conditions. Another person can challenge it, misunderstand it or improve it. A public release raises the stakes further.

Liz and her team built a campaign around that movement from private to public because millions of ordinary Dropbox shares contain some version of that risk. The action looks functional on a screen, but the person clicking the button may be handing over something they have spent months making.

That vulnerability shapes how Dropbox works with creators. A conventional partnership might begin with a detailed brand brief and ask the creator to reproduce the company’s message in a familiar voice. Liz takes a completely different approach because the creator understands the audience the brand is trying to reach.

Fred’s community knows how he speaks and what he finds worth showing. Replacing that voice with Dropbox language would make the work less credible. Liz’s team reviews partnerships for product inaccuracies and would intervene over offensive material, but it generally does not rewrite the creator’s point of view.

Her clearest instruction is also the best test of the finished work: “If this feels like a commercial, we’ve failed.”

The content still has a job to do. It should teach people something, entertain them or give them material they can use. Dropbox may be visible, but the audience should not have to endure an advertisement to reach the useful part.

The company applies the same thinking beyond household names. Dropbox Studio funds projects from customers at different stages, including an Oakland-based rapper named Fijiana, whose music video was made with friends and supported through the program. Liz likes that the platform can document an established artist’s archive while also helping someone make the work that may eventually establish them.

The difference matters because early creative work carries a different kind of exposure. A famous artist can share an old draft after an audience has confirmed the value of the finished product. An emerging artist shares without that protection.

More output raises the value of judgment

The willingness to give creators room depends on judgment. Liz sees the same need becoming more visible as AI expands the amount of work a marketing team can produce.

Her team uses AI to remove friction from parts of the campaign process that once consumed time and budget. Research that might have run once can now happen four or five times while a campaign is being developed. Synthetic research tools send concepts to real people, analyze the responses and return findings within roughly 48 hours.

The brand team also built a live site that collects performance data, brand tracking, lift studies and other metrics. Leaders can review the information without waiting for employees to spend 20 or 30 hours each month building another reporting deck. Designers can avoid some of the repetitive work of generating the same asset in dozens of sizes.

Liz values those tools because they give the team more chances to improve the work. They do not settle the harder questions. A system may generate 50 options, but someone still has to decide which one fits the audience, which joke sounds forced and which concept resembles everything already in the market.

“The models are fed with history, not future,” Liz says.

That limitation becomes more important as production gets easier. AI can assemble familiar patterns quickly because it has access to so many of them. Creative teams still need a point of view that tells them when familiarity is useful and when it has become repetition.

Liz does not believe taste develops through prompting alone. People learn by watching experienced practitioners choose, discard and revise. Art schools use critique for that reason. Young designers need to see what their more experienced colleagues notice and understand why a visually attractive solution may still fail to function.

The same principle applies to customer research. Data can narrow the possibilities, but it cannot replace the judgment required to interpret what people are saying, what they are avoiding and what they may not have words for yet. Liz wants technology to create more opportunities for that work, not remove the person responsible for doing it.

The infrastructure beneath the finished work

Dropbox will reach its 20th anniversary with a product many customers first encountered as a place to store files. Liz is trying to show the larger role it has played all along.

A filmmaker sends a cut for feedback. A design house opens an archive. A musician hands fans the content they did not need to record. An emerging artist shares a project that has not yet been endorsed by the market. In each case, Dropbox sits between the private act of making something and the public life that follows.

At Fred’s show, the folder arrived after the concert. By then, the audience had already received the more valuable benefit, the gift of presence. They had spent the night looking at the stage instead of their screens, trusting that the files would be there when they needed them.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

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Rick Galasieski arrived at Talladega prepared to explain Super.com.

The company had become an official savings partner of NASCAR and set up an activation where fans could learn about its products. Rick assumed most visitors would be meeting the brand for the first time. Then people began walking up to the tent, opening the app on their phones, and showing him that they were already members.

He adjusted the conversation. Instead of explaining what Super.com was, he began asking which parts of it they had used. A customer who knew the travel product might not know about cash advances, earnings tools, or credit building. What looked like a broad awareness campaign became a chance to help existing members understand more of the company they had already joined.

Over five years at Super.com, Rick has watched the business move through a series of growth stages that demanded different answers. Travel created acquisition. Membership extended the relationship. A wider set of financial products made retention and cross-selling more pressing. NASCAR entered the picture when Super.com believed familiarity and credibility had become constraints of their own.

Every product is at a different stage

Super.com began as SnapTravel, a company focused on discounted hotel bookings. By the time Rick joined, travel had already become a reliable way to bring customers into the business. He came in to build embedded financial products around that base, including cash advances, credit-building tools, an earnings platform, and a digital wallet.

Rick does not evaluate all of those products through the same set of numbers. He first considers where each one sits in its life cycle. A new product has to prove that customers can be acquired at a workable cost. A product with several years of history faces a different challenge: keeping those customers long enough to support the economics.

Travel has nearly a decade of operating history behind it. Super.com’s cash advance product has been running for about three years, giving Rick a clearer view of acquisition costs, channels, and the levers available when the company wants to increase volume. The newer credit-building product is still establishing those basics after more than a year spent working through compliance and regulatory requirements.

That makes a debate about customer acquisition cost versus lifetime value too simple for Rick. Both matter, but not in the same way at every stage. When Super.com introduced its membership program, the company tested three price points and tracked conversion, retention, customer acquisition cost, lifetime value, and return on ad spend before deciding how to iterate. The metric follows the question the product still needs to answer.

This life cycle view also helps explain why Super.com began spending more heavily on brand. Its performance channels still worked, and the company could continue acquiring customers through travel and other product-specific entry points. Rick believed the larger opportunity required more people to recognize the company and feel comfortable exploring a broader relationship with it.

Brand needs a defined job

Super.com did not choose NASCAR only because Rick likes sports.

The company studied the audience and saw a close match with the customers it already served: everyday Americans trying to save money, stretch their income, or improve their financial position. NASCAR offered reach and credibility with a community that had a strong relationship with the sport and its partners.

That credibility became more useful as Super.com grew beyond the product that first introduced it to customers. A company called SnapTravel could explain discounted hotels, but it could not easily hold travel, cash advances, earnings, credit building, and a membership program under one identity. Super.com hired agencies and consultants, studied customer personas, narrowed a list of possible names, and chose a domain it did not yet own.

The domain purchase was well worth the investment, returning far more than the initial investment. The name works as the company’s identity, website, and message. A billboard can say only Super.com and still tell people where to go. That simplicity became more valuable as the product expanded.

The NASCAR relationship followed similar logic. Super.com had already experimented with airport, subway, and sports advertising, but NASCAR offered a more concentrated customer fit. The partnership also required approval from both sides. NASCAR vetted the company before associating its brand with Super.com, adding another layer of credibility to the arrangement.

At Talladega, Rick found that many fans needed no introduction. Their familiarity did not make the activation unnecessary. It changed what the company could do with the interaction. Once he knew they were members, he could focus on the products they had not yet discovered.

The front door should lead somewhere

Travel remains one of Super.com’s most effective entry points.

A customer looking for a hotel may find Super.com listed beside larger travel platforms at a lower price. During checkout, the company offers the option to join Super Plus for $15 per month and receive an additional 10% off that booking and future hotel reservations. According to Rick, the program is approaching 1 million paid members.

The membership gave Super.com a way to extend the relationship beyond a single trip. It also made the rest of the product ecosystem more consequential. Someone who enters through travel may later use credit building. Someone who arrives through cash advance may need a way to earn additional money. The value of acquisition increasingly depends on whether the company can make the next product relevant.

Super.com recently rebuilt its home page around that question. The company knows which product brought a customer into the ecosystem and uses machine learning to determine what to show next. A customer who arrives through cash advance is more likely to see the earnings platform because the original behavior suggests an immediate need for money. Rick says the first version has already increased engagement and return visits to the home page.

He has also spent years pushing teams to repeat key messages more than they think necessary. A product manager may see a call to action sitting plainly on a page and assume the customer has noticed it. Rick assumes many people have not seen it, understood it, or encountered it at the right moment. That is why the same recommendation may appear through the home page, customer relationship management messages, and other prompts across the experience.

Each interaction is meant to make the path through the product clearer. The membership gives customers a reason to stay, while personalization helps determine what they should see when they return.

Speed needs a feedback loop

Super.com moves quickly, but Rick does not treat speed as evidence that a decision is right.

Early in his career, during the dot-com boom, he and a partner wrote a business plan and raised $2 million within weeks. The company grew to more than 200 employees before closing when the market turned and its burn rate became unsustainable. The experience taught him how easily capital and momentum can hide weak economics.

At Super.com, the operating model shortens the time between an idea and reliable evidence. Teams test pricing, customer flows, ads, and landing pages, then use the results to determine what deserves more investment. Growth employees sit within product teams, while finance, product, and marketing review performance against shared objectives. Rick is wary of marketing metrics that look successful but do not support the product or financial targets above them.

That structure allows the business to move quickly without separating experimentation from accountability. Rick may use instinct to identify where to look, but he expects the data to determine whether the company continues. His role reinforces that discipline. As general manager of financial products and earnings, he owns the profit and loss statement for Super.com’s non-travel businesses, so marketing spend eventually has to connect to revenue, retention, or product adoption.

The company applies the same approach to artificial intelligence. Super.com expects employees to use AI tools, provides internal training, and asks teams to demonstrate agents and workflows during weekly reviews so others can reuse them. Rick now uses Claude, connected to internal analytics systems, to answer some data questions that previously required waiting for an analyst.

The value is the time recovered between seeing a problem and learning whether the proposed answer works. Travel showed Super.com how to acquire customers. Membership gave them a reason to return. Personalization now helps decide what each customer should encounter next.

Rick’s job is to notice when one question has been answered well enough to start asking another.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

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A few weeks before Jean Brandolini-Lamb sat down for this conversation, an AI hardware company called Cerebras went public. For EquityZen, where Jean serves as CMO, the IPO was more than a headline. It was proof of concept. About 1,400 individual investors had bought into Cerebras through the platform starting in 2020, six years before the listing. The minimum investment was $5,000. The average price per share was roughly $32. At IPO, the stock opened at $185 per share, a 5.6x return.

These are the numbers that justify EquityZen’s entire mission. And Jean cannot use them to promote a single deal.

EquityZen operates in one of the most heavily regulated corners of fintech. Jean cannot recommend specific investments, cannot send targeted communications about deals unless users have explicitly expressed interest, and cannot deploy the kind of aggressive language that drives conversions in less regulated categories. The tension at the center of her job is both simple and relentless: how do you grow a platform when most of your audience doesn’t even know your market exists?

From Galleries to Growth

Jean didn’t take a straight line to fintech. She graduated with a degree in art history and spent her first years managing galleries. “I decided the part of it I liked the most was really the PR part, the comms part, the doing the marketing, trying to get reporters to write about what we were doing,” she said.

That instinct carried her from galleries into public relations, then into technology and financial services at institutions including JP Morgan and TIAA. She watched how the wealthy invested through special purpose vehicles designed for high-net-worth clients. When she joined EquityZen, she saw something different.

“I was amazed. I was like, wow, these guys figured out through processes and technology to take these same special purpose vehicles that used to be accessible only to the very wealthy, and they found a way to make them available to just your average accredited investor.”

EquityZen, now part of Morgan Stanley, is a two-sided marketplace that enables accredited investors to buy shares in private companies before they go public. On one side are shareholders, typically early employees or investors who need liquidity for personal reasons: a down payment, student loans, or in one case, a CEO who sold shares to fund a scholarship program. On the other side are investors looking for exposure to private-market companies, often in technology and AI. The platform’s purpose-built technology for manufacturing SPVs at lower cost allows it to offer minimums as low as $5,000, while competitors often start at $100,000 or more.

Category Awareness Before Brand Awareness

Jean manages three distinct audiences: individual investors, individual shareholders, and the private companies themselves. Each requires different messaging and different relationship-building. But before any of that work can begin, she faces a more fundamental challenge. Most of the eligible population doesn’t know the market exists.

“We’ve always been driven by the idea that we can’t lead with brand awareness. We have to lead with, we have to build category awareness.”

She has a simple test for this reality. “When someone new comes to work here, I say, did you know that you could invest in a private company before you came here? And most of them are like, no, and I told my friends and they couldn’t believe it.”

This shapes every growth decision. Rather than promoting individual deals, EquityZen invests in education. The company became one of two data partners with Yahoo Finance when the publisher began covering private companies. Investors can now search a top private company on Yahoo Finance and find information sourced from EquityZen. The partnership was built on a straightforward insight: if people are going to discover private investing, they’ll start where they already go to research public stocks.

In most consumer companies, a 5.6x return story would be the centerpiece of every ad campaign. At EquityZen, the compliance framework makes that kind of promotion impossible. Jean cannot market specific deals or send targeted communications unless a user has indicated interest first. Drew, the host, compared the dynamic to winning the World Series but not being allowed to yell about it.

Jean’s response was practical: “I think it just drives us to be more creative.”

She sees the constraint as productive. “We don’t think about compliance as someone who says yes or no. We think about compliance as our partner to help us get the word out.” In practice, compliance requirements pushed EquityZen into a consent-based, interest-driven marketing model. Users click a button on the platform to indicate interest in specific companies or categories. That zero-party data determines what communications they receive. “The more information you give us, the more relevant the communication we have with you can be,” Jean said.

The result is a deliberate filter.

“Maybe we really just want to reach the people who belong here and should be here and who are educated and want to educate themselves more. Rather than trying to reach everyone who’s looking for the next hot thing, we actually want to reach the responsible investor who is interested in some diversity and wants to invest in technology they believe in.”

Content Built from Questions

Jean’s content strategy mirrors the same education-first approach. EquityZen built a deep help center sourced entirely from real customer questions.

“We look for questions that new clients ask us. We look for questions in search and we answer those questions because there really wasn’t, before we started, one place where you could go to learn about investing in private markets.”

That library of long-form content created an unintended advantage. When AI-powered search engines began surfacing results from across the web, EquityZen’s education-first archive started ranking. “When we started this blog, no one was talking about AI search,” Jean said. “And then suddenly AI search started being a thing and we were like, oh, wow, long-form quality content actually helps you with search. That wasn’t our goal when we started. Our goal was to really help people.”

Marketing and product operate as a single unit. Jean described her relationship with product partner Sudeish as “inseparable,” noting that he was her first phone call of the day.

“Our product is what we offer. It’s our experience. But marketing and content is such a core part of that because people aren’t just seeking product, they’re seeking information.”

The teams share data across business operations, product, and marketing, looking at deal performance alongside action cards that help users form deeper relationships with the platform.

Where Accessibility Meets Ambition

If Jean had $100,000 with no compliance constraints, she would invest it in video. “Podcasts, in-office production, following the founders, clipping. We do video. I think I’m paying for more of our videos to be out in the world.”

Her team remains “small but mighty,” and she hires for adaptability over domain expertise. Some members came from regulated industries; others didn’t. “We’re always focused on why we’re trying to do something and maybe why we can’t from a compliance perspective and then see if we can get some common ground.”

With EquityZen now part of Morgan Stanley, Jean sees the integration as a chance to scale the company’s original mission. Morgan Stanley covers the private markets more broadly than any other institution, and Jean views that reach as an opportunity to bring accessible private-market investing to an even larger audience.

For a CMO who started in art galleries and found her way to one of fintech’s most constrained categories, the work has always come back to one question: how do you welcome people into a market they didn’t know existed? At EquityZen, 1,400 Cerebras investors and a 5.6x return suggest she’s found a working answer.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

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Ashley Kiolbasa didn’t hesitate when she told a crowd gathered on the rooftop terrace at 2 Penn that the rules of marketing have been rewritten.

“We as people have stopped browsing the internet completely. We’ve offloaded that chore to AI without even thinking about it, and that fundamentally changes the customer journey.”

She was one of three marketing leaders on stage at the Big Leap VIP Experience during New York Fintech Week, where CMO Uncovered recorded a live panel conversation sponsored by CleverTap. Nicole Casperson, Founder and CEO of Fintech Is Femme, moderated an ESPN-inspired round robin panel designed by Drew Glover, Co-Founder of Fiat Growth:

• 5 provocative topics

• 3 operators

• 0 rehearsed answers

The panelists: Veronica Mendoza, VP of Growth Marketing at Betterment, an online investment platform making financial advice accessible and affordable. Kathryn Flynn, VP of Marketing at Zip, a buy now, pay later company focused on serving America’s underserved population. And Ashley, the CMO of Prove, a digital identity company that helps businesses verify people are real.

Before the panel kicked off, Anand Jain, Co-Founder of CleverTap, took the stage to mark Big Leap’s second year. “In the world of notifications, emails, everything that you can’t see and touch, we have launched a magazine,” he said, holding up CleverTap’s first print publication to cheers from the crowd.

Your Next Site Visitor Runs on a Large Language Model

The opening topic was blunt: AEO is the new SEO. The panel agreed, then pushed further.

Veronica set the frame. “AEO is not just the new SEO, it’s the new search, sort of wholesale,” she said. “People are using LLMs as their entry point all the time.” Marketers now need to show up in the conversational layer that LLMs pull from: Reddit, review sites, and press. “If you’re not there, you’re just gonna be missing entire swaths of users.”

Kathryn split the challenge in two. Human discovery still works the way it always has: great content, consistency, brand work people talk about. But agent discovery is a different problem. At Zip, her team is preparing for a world where autonomous agents make purchases on behalf of humans. “For us, it starts with governance. It starts with security,” she said, pointing to trust frameworks and identity preservation.

Ashley landed the point with a specific example. Her team at Prove adopted Scrunch, an AI search optimization tool, to monitor how the company appears in LLM-generated responses. One finding caught her off guard.

“Last week I learned that our competitors were being cited more often because they have Wikipedia pages. Now my team has the mandate to go create a Wikipedia page, which I can’t imagine having asked them to do six months ago.”

High-Trust Channels and the 3X Content Play

The second topic tested whether the traditional funnel is dead.

Ashley reframed the question around trust instead of structure. What changed is not that the funnel broke but that low-trust channels cratered. “Some of the low-trust channels, cold outbound, have gotten so bad that we feel comfortable ignoring them completely,” she said. When she joined Prove a year ago, her first two investments were customer marketing and community, then partner marketing. “Whenever we can have a customer speaking on our behalf, we want to create that platform for them to do that.”

Kathryn had the data. Zip launched a customer ambassador program where real customers create content in their own homes, sharing honest takes on why they use the product. “We have seen such strong engagement rates to that content, 2X, 3X what we’re seeing from actor or static,” she said.

Veronica pushed back on calling the funnel dead. “Maybe not necessarily that it’s dead, but that we’re all reckoning with the fact that it was always kind of an oversimplification,” she said. At Betterment, she tracks account-based marketing prospects who move “two steps forward and one step back” through their journeys. The goal is to be present at every stage, not to force people through a linear path. She pointed to Betterment’s B2B campaign built around SpongeBob SquarePants, a nod to CEO Sarah Levy’s history as COO of Nickelodeon.

“B2B customers are not just B2B buyers. It’s important to respect that people could be sitting on their couch at night and see something amusing from one of your B2B solutions.”

Taste, Bravery, and the Sea of Sameness

When every team can generate thousands of assets with AI, the panel agreed: production is no longer the constraint. Differentiation is.

Ashley tied the challenge directly to Prove’s mission. “Authenticity really becomes the moat, and taste is how you build that authenticity,” she said. For an identity company whose entire purpose is helping people prove they are real, operating in a world of AI-generated content carries a specific weight. “We have no choice but to operate by that standard ourselves.”

Kathryn argued that taste extends well beyond campaigns.

“The brand is not just the campaign. The brand is how your product works. It’s their product working every single time someone goes to use it at a critical moment in their day.”

Veronica screens for taste during hiring. What she pushes her teams toward is bravery. “Can you not worry too much about what has worked in the past or looks the same as everything else?” she said. “Let’s take a big swing and learn fast because now we have the luxury of time.”

Don’t Shrink the Team. Multiply It.

The fourth topic pushed back on the narrative that AI-native marketing teams must be smaller.

Ashley cut through the noise immediately. “If your team does not look like five marketers and 100 agents, you’re fine. Normal,” she said. She called out a growing, unspoken pressure. “A lot of marketers are silently sitting in AI shame jail right now because they feel like their team should look different than it does.” Her team at Prove is 25 to 30 people, and she has no plans to reduce it.

“The things that move the needle right now still require humanity.”

Kathryn pushed the conversation to a structural level. “It’s rethinking completely how this team operates,” she said. “What is this team accountable for delivering? And where in that system does the human judgment need to sit?” As AI removes the resource constraint, the real challenge shifts to decision-making: teaching more junior people how to make strategic calls they have never had to make before.

Veronica described the AI-native org as resembling “the scrappy and lean startup marketing orgs of the past,” but with a meaningful upgrade. Marketers can redirect time from execution to strategy. “The question starts to become less of ‘can we get it all done’ and more of ‘are we doing the right things?’”

Attribution Was Never a Perfect Science

The closing topic was the most provocative prompt of the night: is attribution is a lie everyone keeps paying for?

Veronica did not need convincing. “I have always been an attribution skeptic,” she said. She started her career in search marketing at the dawn of pay-per-click, the clearest attribution line possible: last click to purchase. But as she moved up funnel, the clarity disappeared. “If any vendor was promising clarity, it felt very disingenuous to me. It would be based on a set of assumptions that were clearly going to be biased. There was never a perfect science here, and there has just always been a lot of hand-waving, and it was all in the pursuit of credit.”

Her solution: stop chasing perfect attribution and align with finance. “When we can align with our buddies over in FP&A on CAC, on ROAS, it gives you the freedom to play within those constraints and take the swings that you can afford to swing at,” she said. That alignment breeds better cross-team partnership because everyone operates toward one goal instead of fighting over credit.

Kathryn traced the problem back to its origin. “I blame the beginning of digital marketing for this,” she said. “CMOs were finally able to go to their CFO friends and say, ‘Look what we can do now.’ That was really exciting. That probably wasn’t very true then, and it’s certainly not true now.” The answer is not better dashboards. “It’s about unlearning that truth and relearning a new set of truths that are credible across your organization so that there is that collective buy-in.”

The panel also called out the structural incentive problem: media vendors report on the efficacy of what they sell in silos, and when CMOs try to stitch those reports together, the result is what one panelist called “a little bit of a house of cards.”

Glasses Up on the Rooftop

Nicole closed by asking the crowd to raise their glasses. “We went through the round robin. They were honest,” she said, noting with a laugh that the panelists were drinking water.

Across all five topics, every panelist landed in the same place: the tools keep changing, but the decisions that matter, what to prioritize, what to say, and how to earn trust, still belong to people.

Ashley put it most succinctly when describing the new reality of site visitors.

“In a world that runs on AI, the most important visitor that’s landing on your site now is not even human.” The challenge for CMOs is making sure the humans behind the strategy still are.

This season of CMO Uncovered is supported by CleverTap. CleverTap is the world’s leading engagement platform, helping brands build meaningful relationships through data-driven personalization. Powering over 2,000 customers globally, CleverTap’s AI-powered engine processes billions of data points daily to help marketers predict behavior and automate engagement at scale. From onboarding to advocacy, CleverTap provides the infrastructure needed to optimize every stage of the customer journey. For the CMOs building the next generation of iconic brands, CleverTap offers the precision and scale required to win in a crowded market. To learn more, visit clevertap.com.

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When Demand Is Not the Problem

Neu Money’s credit card was nine months old when the affiliate channel started producing applications at a pace the team had not expected. The demand signal was there. Yogesh Mehra’s response was to slow down and look harder at who was actually applying.

“The demand is not the problem,” he says. “The right kind of demand is what we are optimizing for right now.”

Neu is a credit card built for two groups of underserved customers: people who are new to credit, including students, recent graduates, and recent immigrants; and people who have experienced financial hardship and are working to rebuild. In both cases, Neu can only deliver on its promise if the customer coming through the door is someone the product can genuinely serve. Volume without fit could weaken the unit economics and undermine the mission entirely.

That pressure, acute at any startup but more consequential here given Neu’s customer base, is where Yogesh’s marketing philosophy begins.

A Product Designed to Be Outgrown

“I did not have a credit card for many, many years,” Yogesh told us. “I have a chip on my shoulder and I want to do something about it.” The experience of being credit-invisible in a system that assumes everyone already has a score informs how he reads customer reviews, sits in underwriting meetings, and defines what a successful customer outcome actually looks like.

His path to Neu was a deliberate accumulation of builder experiences across institutions of very different sizes. At First Republic Bank, he was brought in to build and grow the marketing for Eagle Lending, an internal consumer lending fintech focused on professional loans and student loan refinancing, operating with startup-like velocity inside a large institution. When JPMorgan Chase acquired First Republic, Yogesh served on the transition team. Alongside his institutional roles, he built advisory and mentor relationships at both Techstars and Plug and Play, two separate startup accelerators, working with early and late-stage founders before stepping into a true founding-stage seat himself. “I thought I was ready,” he says of joining Neu.

“And we have done very well. But a true zero to one in a startup is unbelievably hard. It is pushing multiple boulders up the hill with little to no direction and little support. And that is very different from being in a startup role inside an established institution.”

Neu serves those two distinct customer groups through a framework Yogesh calls the graduation ladder: a defined progression from a thin or damaged credit profile toward a score that opens real financial options.

“What does success look like to the customer?” he asks. “Were we able to get customers there? Were we able to make a meaningful difference in the financial wellness of the customers over a certain period of time?”

The graduation ladder also explains why acquisition quality carries so much weight at Neu specifically. The product can only deliver on its graduation promise if the customer who comes in the door is someone whose profile the product actually fits. Acquiring the wrong customer does not produce a bad quarter. It produces a customer Neu cannot help, which defeats the purpose of the company.

The Quality Problem: Why Paying More Is Sometimes the Discipline

That framing puts a familiar industry concept in sharper relief. “The CAC trap is when you do not consider the quality of the vintage that you get from that channel,” Yogesh says. A channel can look efficient on the surface while delivering customers whose actual lifetime value (LTV) makes the economics deeply unfavorable. Optimizing for customer acquisition cost (CAC) alone measures the cost of acquiring a customer without accounting for the value that customer produces over time.

The correction, in Yogesh’s framework, is the LTV-to-CAC ratio: measuring the lifetime value of the customer relative to what was spent to acquire them.

“If you layer that dimension, you’ll make a very different decision... It’s totally okay to pay a little bit more to get the right kind of customer in the door. Even if you have to pay up a little bit, that’s the right trade-off.”

He extends that argument to paid acquisition as a long-term growth foundation. “Paid acquisition channels are an addiction and a tax on weak product defensibility,” he says. The channels themselves have become less precise over time, as third-party cookie deprecation limits targeting and privacy constraints tighten. The auction-based nature of digital media means that every competitor who throws budget at growth drives up costs for the whole market. In Yogesh’s observation, cost per thousand impressions (CPMs) have risen between 4% and 7% annually over the last decade.

“If your growth is coming from putting money in an auction, that’s not the best way to grow in the long term.”

The acquisition mix Yogesh is building at Neu favors channels with better structural durability. Third-party publications covering Neu offer higher credibility rather than the company promoting itself. “Somebody else talking about us is better than us talking about ourselves,” he says. App store reviews reflect the same sentiment, with customers writing that nobody took a chance on them before Neu did. For Yogesh, those reviews are both a brand signal and a measure of whether the graduation ladder is working.

Yogesh is also focused on where discovery itself is heading. He writes publicly about generative engine optimization (GEO), the discipline of ensuring a brand surfaces in AI-generated answers and large language model (LLM) outputs, not just traditional search rankings. His approach centers on earning credibility through third-party validation and building an authentic presence in the spaces where real financial conversations happen.

“Discoverability is very important,” he says. “Where discovery happens is going to shift over time."

Building the Team for What Comes Next

In his Substack article “5 AI Marketing Roles That No One is Hiring For (Yet),” Yogesh laid out a vision for how marketing departments will need to reorganize around artificial intelligence. He has since started building toward that vision at Neu, and his framework divides future marketing work into three lanes.

The first is human-led, covering strategy, ethics, judgment, and the fair lending guardrails that carry particular weight in a regulated fintech environment. The second is fully agentic, where AI handles programmatic media buying, landing page variations based on customer personas, and the orchestration of repetitive execution tasks. The third is a hybrid zone of co-creation, where humans and AI iterate together on creative concepts and messaging.

“Things that would have taken me three to four times as many people, we are doing right now because we have been able to orchestrate some of that work,” he says.

His approach to hiring reflects the same framework. As a guest faculty member at San Jose State University, Yogesh tells students the same thing he applies to his own team decisions. “Don’t focus too much on the tools. Focus on the frameworks, focus on the critical thinking, focus on the broader disciplines.” The concern running underneath that advice is specific. Leaning on AI too heavily, without maintaining genuine analytical effort, gradually erodes the thinking the tools are supposed to support.

“When I use AI too much without thinking too much, I feel like I get dumber over time and there are now conclusive studies to prove that.”

Graduation as a Growth Strategy

Neu's belief is that underserved credit customers deserve to be treated with the same respect and transparency as any other borrower from day one. When you lead with honest expectations and a clear path forward, the customer relationships that follow naturally become your strongest growth engine

“The best way to understand these customers is to go beyond the numbers and talk to them. Really understand what their day looks like.”

Transparency, the right product fit, and the graduation ladder make that possible. And for Yogesh, every acquisition decision, every channel trade-off, every debate about CAC and LTV, ultimately comes back to the same question: did the right person come through the door, and were we able to make a meaningful difference in their financial life?

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When Your Best Customer Has Never Heard of You

Andrea Leewong has a marketing problem most CMOs never face. The company she represents has likely already touched 20% of U.S. small businesses with employees via platform partnerships. Its products sit inside platforms that millions of restaurant owners, fitness studio operators, and e-commerce sellers open every single day. But almost none of those people know Parafin’s name.

“It’s called DoorDash Capital. It’s called Mindbody Capital,” Andrea says. “Here and there, there’s a little bit of information about Parafin.”

For most of her career, Andrea worked in businesses where the entire model depended on being seen. At NerdWallet, organic search was the focus every function in the company worked toward. At Opendoor, personalized direct mail placed a specific dollar offer in someone's hands. Visibility was the mechanism. Now she runs marketing for a company that operates, by design, in the background. She’s navigating a fundamental tension point: how do you build brand equity for something that is structurally invisible, and should you even try?

Her answer is yes. But the path to get there is unlike anything in her prior playbook.

Meet Andrea and the Company She’s Building For

Andrea joined Parafin after years working across some of the more data-intensive marketing environments in fintech and real estate. NerdWallet taught her what it looks like when an entire company locks onto a single growth objective. “Everyone across every function was driving to that goal of organic search,” she recalls. “I haven’t seen that level of alignment and ownership across a company before.” Opendoor taught her the power of a personalized, well-timed offer delivered at the exact moment someone is ready to act.

Both experiences shaped how she thinks about the small business financing problem Parafin is trying to solve. Small businesses, she explains, have historically been misclassified. They are too small to qualify for enterprise lending, yet too complex to be treated like consumer borrowers. Banks have long defaulted to evaluating them through the lens of the owner’s personal credit score, personal guarantees, and personal financial exposure.

Parafin works differently. The company embeds its lending infrastructure directly inside the software platforms that small businesses already use to manage their operations. A restaurant running on DoorDash generates real revenue data inside that platform. Parafin builds data-sharing agreements with partners like DoorDash, Mindbody, and Jobber to run machine learning models against that anonymized transaction data. The underwriting is based on how the business actually performs, not on who owns it.

“It doesn’t matter who the owner is, actually,” Andrea says. “We think that creates a more inclusive approach to financial services.”

The company handles underwriting, servicing, customer support, and the full lending lifecycle. The platform partner handles the relationship with the merchant. Parafin handles everything behind it.

The Engine: Two Acquisition Problems Running in Parallel

What makes Andrea’s job structurally unusual is that Parafin has two entirely separate acquisition challenges happening simultaneously, and progress on one does not automatically produce progress on the other.

The first challenge is enterprise B2B acquisition. Before a single small business can access a Parafin product, the company must first land a partnership with a major software platform. These integrations are deep, complex, and slow to negotiate. “You cannot easily launch a deep integration with Amazon,” Andrea notes. That difficulty is also the moat. Once a partnership is operational, it is not easy for a competitor to replicate.

The second acquisition challenge is what happens after the integration goes live. Getting a small business owner to notice, trust, and act on a financial offer inside a platform they use for something else entirely is its own problem. The best version of that moment, in Andrea’s view, is one where the offer is contextual and appears at the exact point of need.

She points to Parafin’s partnership with Gusto, the payroll platform, as a concrete example. Small businesses can access a line of credit right at the moment they need it most to ensure their teams get paid on time. “A lot of times it’s really about cash flow,” Andrea says. “It’s not that they don’t have revenues coming in. It’s a matter of customers maybe not paying them for a few weeks.”

The offer often reaches businesses that were not actively looking for financing but are genuinely well-positioned to use it. “We find that we are able to attract better businesses because of that,” she says.

Outside of those embedded moments, Parafin uses email triggers and platform notifications to drive awareness. Andrea is also exploring direct mail, drawing on her Opendoor experience, where personalized offers delivered to physical addresses converted well. The translation is not one-to-one. “Who is the recipient of the mailer? Is it actually someone who can make a decision or is it someone who’s just working at the business?” She is testing, not declaring victory.

The Craft: Brand as a Competitive Moat

For most of Parafin’s history, the question of brand was largely set aside. The company was infrastructure. It was white-labeled. It did not need a name in the market. Andrea’s arrival signals a shift in that thinking, and she credits her CEO and founder, Sahill Poddar, with pushing it forward. Sahill shared an article with her about the luxury watch industry, in which brands that competed on precision and technical specs eventually found those differentiators commoditized. The ones that endured did so on the strength of something harder to copy.

“We can’t just, and we don’t want to, compete on features,” Andrea says. “I don’t think we can necessarily claim to be the only ones who can ever do it.”

The brand she is building has two audiences. Platform partners need to see Parafin as a design partner, a company that goes above and beyond on integration, ease, and long-term commitment. Small businesses, once they encounter the product, need to feel that the company behind it cares about their actual situation.

When asked which brands she admires, Andrea does not cite a financial services company. She mentions Trader Joe’s. “They are so consistent. They have a whimsical nature to them. I’m literally shopping for groceries, and it shouldn’t be that exciting, but it’s so fun.” She also mentions Costco: unwavering in its identity, clear about what it stands for, committed to the members who keep coming back. “You know who they are and you know what they care about.”

In the B2B space, she points to Ramp. She admires how Ramp uses individual voices within the company, its founder, its chief economist, its team members, to carry ideas that resonate more than a brand speaking to itself. She also notes how Ramp has found a tone, light enough to be entertaining, serious enough to be trusted. “They’ve toed the line with some lightheartedness, but people take them seriously still.”

For Parafin, she does not think humor is the right register. The subject matter is financial pressure and the audience is people who work hard and have a lot on the line. The brand, when it fully emerges, will need to reflect that seriousness while still feeling like a partner rather than a vendor.

The AI Question: Treating the Tool Like a Junior Analyst

Andrea’s most direct advice to other marketers has nothing to do with channels or campaigns. It is about how to use AI to answer the questions marketers always have but rarely get answered.

“Marketers often do not have enough access to data scientists,” she says. “I think that is a significant, significant unlock.”

Parafin has connected its enterprise AI tool directly to its backend database, giving Andrea’s team the ability to ask questions in plain language against a dataset covering millions of small businesses. She is careful to frame what that actually looks like in practice. “It is a back-and-forth dialogue and a conversation with AI. You need to not be lazy and take V1. You need to probably be getting to V10 or V15 or V20.”

The mental model she uses is direct: treat the AI like a talented junior analyst who is excellent at certain things but does not yet know what matters. The marketer still supplies the judgment, the taste, the knowledge of what an interesting insight would actually look like. The tool helps surface patterns and validate directions faster than a SQL query submitted to an overstretched data team.

The Open Question Ahead

The most candid moment in the conversation comes when Andrea describes the challenge that does not yet have a clean answer. Parafin has strong distribution through its platform partners. It has proprietary data that most lenders could not access. It has a defensible model. What it does not yet have is a name that small businesses recognize or seek out on their own.

Some of them find Parafin anyway. “People are still going directly to our website and actually filling out a form,” she says. That direct pull is a signal, a small one, but a real one, that the brand has value even before it is fully built.

Her task now is to close the gap between the infrastructure Parafin has already built and the identity it has not yet claimed. In a market where platform partnerships take years to develop and underwriting models run on data that competitors cannot easily replicate, brand may be the last remaining differentiator that is both meaningful and genuinely hard to copy.

“The sum total of experiences that a person or a company has with you,” she says, “is probably more important because of how easy it is to spin things up these days.”

Andrea is building for a future where platform decision-makers and small business owners know exactly who Parafin is and choose it because of that knowledge. The infrastructure is already there. The name is still catching up.

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The Moment the Story Changed

Alex Braman will tell you that Greenlight’s customers handed him his biggest strategic challenge without knowing it. Parents who had trusted Greenlight with their children’s spending were coming back with a different kind of question. Not “how do I set a spending limit?” but “how do I know where my kid is right now?” They weren’t asking for a better financial product. They were asking Greenlight to solve the next problem in their lives because they already trusted the company with the first one.

That shift, from a company known for a debit card for kids to something that might be called a family technology platform, is the defining challenge Alex is working through today as the CMO of Greenlight. It raises a question that sits at the heart of modern growth marketing: when your product is expanding beyond the category that made you, how do you tell a new story without abandoning the one that built your audience?

“How do we take ‘the debit card for families’ and move it toward a financial and technology platform for families?” Alex said. “We’re thinking through how we communicate that. It’s still a little clunky, so we’re working on it.”

That honesty is characteristic. Alex is not a marketer who reaches for polished language when the work is still in progress.

Meet Alex, Meet Greenlight

Alex stumbled into marketing. His career started in management consulting, building decks for large companies trying to allocate their resources more wisely. He was good at structured thinking and getting ideas to land with skeptical audiences. But marketing came later, almost by accident, and when it did, it stuck because of what he calls the immediate feedback loop.

“With digital, you could test and learn immediately,” he said. “Do truck owners like a picture of a truck on an ad for their mortgage? Turns out, no, they don’t. But they react well when you give them a big number.”

That combination, analytical rigor from consulting and empirical curiosity from early performance work, is still how he operates. He thinks about internal alignment the way a consultant thinks about client management: you have an idea, you know it might face resistance, so you build your case, pressure-test it with data, and get the right people on board before the big meeting. That skill, which he describes as “shepherding and growing ideas until everyone buys in,” translates directly to running a marketing organization where spending decisions require sustained conviction across multiple quarters.

Greenlight, based in Atlanta, offers a debit card and financial platform for children and their parents. Kids get spending controls, chore-linked allowances, a 6% savings rate on the premium tier, and access to educational investment products. Parents get visibility, guardrails, and something harder to name: confidence that they are teaching their children something real about money. More recently, Greenlight has added family location tracking and driving alerts, products that extend the platform into what Alex describes as “a family tech suite that is finance-enabled.”

The trust barrier Greenlight is working against is not skepticism about the product. It is category awareness. Most parents do not think they need a specialized financial platform. They assume the problem is manageable without one, right up until the moment their child wants to spend freely on a family vacation or buy items in a gaming app without a ceiling. Greenlight’s marketing job is to make that moment feel familiar before it happens.

The Engine: Growth in a Noisy Media Environment

Alex runs a media mix that covers paid social, search, display, TV, audio, podcasts, and Reddit. Each channel plays a different role, and he thinks carefully about which channels can serve two purposes at once.

“TV is compelling because you can do direct response and awareness with it,” he said. “And audio is relatively cheap, so you can figure out a way to still get those impressions.” Reddit has become a more deliberate part of the mix, not as a conversion driver but as a top-of-funnel tool. “It’s more like how do you start a conversation with someone for our business,” he said.

On Meta, the team is building analytical models to process creative metadata and flag when the algorithm’s performance starts to shift. The goal is to move from reactive diagnosis to predictive monitoring, using AI to surface patterns in the ad library that would take a human analyst weeks to find manually.

The most interesting growth challenge Alex described is the one every scaling company eventually faces: you’ve captured the people who were already looking for you, and now you need to find the people who don’t know they should be. His approach is demographic and behavioral gap analysis. If women in a certain age range convert strongly through Facebook but men in a comparable range convert better through live events, that difference tells you something about where your awareness problem lives, not just your conversion problem.

“Who should be using your product but isn’t?” he asked. “When you look at persona data or demographic data, you usually will find out that some segment loves you, but another doesn’t, even though the product is good for both.”

Solving that incrementally means protecting an idea long enough to measure whether it worked, which brings him back to the consulting skill set. Getting buy-in for a long-cycle awareness investment requires the same internal storytelling discipline as presenting an unpopular recommendation to a Fortune 500 client.

The Craft: Brand and Performance Are the Same Function

Alex does not separate brand from growth, and he is direct about why.

“If you’re putting a direct response ad out there, it’s still your brand,” he said. “Growth is going to be brand and performance together.”

He owns both at Greenlight, and that structural choice reflects a philosophy: every dollar in the market should serve the dual purpose of telling people who you are and telling specific people why they need you right now. When those two goals operate in separate silos, the creative drifts, and the story becomes incoherent.

The category pivot from fintech to family tech is making that philosophy harder to execute and more important to get right. The new positioning needs to feel earned, not declared. “We need the product to be able to deliver on these promises so that they feel progress from their use of the product, or they feel joy from their kid learning about money,” he said.

That combination of functional value and emotional payoff is what Alex means when he talks about storytelling. A good storyteller, he argues, can entertain, educate, or motivate. A great one can do all three without losing the audience before the arc lands. His example of Liquid Death, a water brand that led people to believe they were buying something edgier than it was, is instructive. The product did not change. The story changed reality around it.

The Road Ahead: Fewer Steps, Sharper Inputs

Alex’s view on AI in marketing is less about what the tools can do today and more about where the leverage will be in 12 to 24 months. He believes the middle steps of campaign production, channel allocation, landing page builds, and creative formatting are already being compressed. What remains irreplaceable is the upstream judgment: what do you stand for, who are you talking to, and why does your story earn attention in a crowded market?

“The execution and solid campaign management, recommending which channel does what, what broke with your pixel, that’s going to be a lot easier to solve soon,” he said. “The remaining extremely valuable talent is nailing the competitive positioning and owning that.”

For his own team, that changes what he looks for in a hire. Process fluency matters less than the instinct to break the process and find a better outcome. A person who has figured out five ways the system fails and rebuilt it each time will always outperform someone who can describe the system accurately. The difference is more obvious now because the tools can handle the description.

Building the Category From the Customer Up

What Greenlight is doing in 2026 is not a brand refresh. It is a category construction project, and the brief came from customers. Parents who trusted the platform with their children’s money started asking it to solve adjacent problems, such as location tracking, schedule management, and the general anxiety of raising kids in a connected world. That trust, built transaction by transaction on the financial product, became the permission structure for something broader.

Alex’s job is to translate that expansion into language that feels natural rather than overreaching. The category Greenlight wants to own, family tech, does not fully exist yet in the way consumers think about it. Defining it, in product, in marketing, and in the story the brand tells every time it runs an ad, is the work of this year and probably the next several.

“Long-term, the category we want to be in and we’re defining is what family tech is,” he said. “What’s the suite of products for a family? And we’re very excited about that.”

The debit card was the beginning. The rest of the story is still being written.

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No Playbook, No Problem.

There is a specific kind of operator who thrives without a playbook. Someone who has been dropped somewhere unfamiliar, forced to orient quickly, and trained by necessity to move before the picture is fully clear. Kendall Bazan is that operator. She just happened to train for it in Siberia.

Meet Kendall

Ask Kendall Bazan for her happy place, and she does not hesitate. It is Berlin, late fall, a cafe table at 7 p.m., German beers on the table, her partner beside her, a show to catch later. Two weeks, no agenda, music in the air. It is a window into someone who genuinely likes being somewhere, absorbed in the texture of a place rather than just passing through it.

This instinct traces back to a Fulbright fellowship in the early 2010s, when she was placed not in the western Russian cities she had been angling for, Sochi or somewhere near Moscow, but in Irkutsk, a city in Siberia on the shores of the world’s deepest freshwater lake. It was, by her own description, a random draw.

She spent 12 months there, experienced negative 40 degrees Fahrenheit, the precise point where the Celsius and Fahrenheit scales converge and came away with something harder to quantify than a credential. “You learn very quickly when you don’t have a playbook and when you’re the singular person doing something,” she says. “You’ve got to learn to move quickly and to adapt a lot within an ecosystem that is changing every day.”

That operating style has carried through everything since. She is now VP of Revenue at Groundfloor Lending, a real estate private lending platform that is actively scaling its borrower acquisition engine from the ground up, and Kendall was brought in to build that program.

The Audit Before the Build

Groundfloor’s lending unit was in its early stages as a standalone business unit under the Groundfloor Finance brand when Kendall arrived. A small number of early-stage marketing channels were running. Her first move was a spreadsheet, not a campaign.

“When I jump in to either building from the ground up or inheriting a small marketing team, I tend to start with an audit. Give me the rundown of everything that we have running or not running right now. Let’s just get it all documented.”

From that baseline, her next step is to identify constraints: which metric are we actually trying to move, and what is the gap between where we are and where we need to be? At Groundfloor Lending, the mandate was clear. Grow the lending pipeline quickly and build a sales motion. That translated directly into a focus on lead and demand, with marketing-qualified leads (MQLs) as the early North Star.

What she discovered was a channel mismatch quietly limiting results. Groundfloor’s brand equity, built over more than a decade, was concentrated on the investing side of the business. The channels that had performed well for a self-directed retail investor audience (content-driven, comparison-site-adjacent, direct-to-consumer) were not a one-to-one match for borrower acquisition.

“I knew exactly where to plug in to get those borrowers,” she says, drawing from nearly a decade spent building the borrower demand engine at the company that would later become Upright, a real estate lending platform she helped scale from 12 people and around $1 million in revenue to $65 million in annual revenue across three business units. “Because you’re right, it’s a smaller, total addressable market that hangs out in very different places.”

Where the Borrower Actually Lives

The first channel correction was directional. Real estate investors, fix-and-flip operators, new-construction developers, and rental-portfolio builders who are Groundfloor Lending’s target borrowers do not spend their days at a desk. They are in trucks, moving between job sites, managing subcontractors, pulling draws on active loans. The content formats that work in traditional B2B SaaS-type demand generation motions do not reach them.

Kendall learned this through ride-alongs. Early in her time at Upright, she joined salespeople on site visits and in conversation with borrowers. “Sit in the car or the truck with your borrower or tail behind them and understand what their day looks like,” she says. It was a revelation that directly shaped her channel strategy.

The formats that actually reached this audience were audio and short-form video content, social platforms where working investors actually spend time, and niche industry communities built around real estate investing. Specialist trade publications and industry directories offered immediate, practical entry points. Paid search, targeted around the specific financing terms real estate operators use when they’re actively looking for capital, was an area where Kendall had scaled results in her previous role and is now building out at Groundfloor Lending.

What did not work: long explainer videos, dense blog content optimized for broad search terms, and any format that assumed a seated, distraction-free audience.

The Deferred Loan: A Product Story That Was Not Being Told

One of the clearest early wins Kendall identified at Groundfloor Lending was a product-differentiation story that had never been told in the right language. The company offers a true deferred payment structure: origination points and fees are financed into the loan, and interest accrues throughout the project and is paid in full at maturity. No monthly payments. For an operator running three or four active projects at once, that means a cash flow architecture that changes how many deals they can carry simultaneously.

“No one else at scale is doing what Groundfloor Lending is doing with a deferred payment product,” she says. “In nearly a decade as a lending marketer, I had never seen it. The product existed. The story didn’t.”

The messaging had stayed internal — operational, structural, lender-speak — without ever reaching the borrower’s actual experience. Her first move was to put a borrower on camera. The output was specific and unscripted: no $16,000 leaving the account every month, more capital available for materials, more deals running in parallel.

That is the approach she brings to product marketing in a commoditized space: stop describing the product from the inside out. Lead with the borrower’s operational reality, then let them describe the impact in their own language.

Loyalty in a Loan: Servicing as a Revenue Function

In real estate lending, the loan closes, and many lenders move on. Kendall’s view is that the close is where the relationship actually begins.

Borrowers draw down on their loans at project milestones. The speed of that draw process — how fast the lender disburses funds once a milestone is verified — directly determines whether the borrower can pay subcontractors, acquire materials, and keep the project moving. Delays are costly in ways that compound quickly across a portfolio.

“Being in lockstep with our servicing team and treating them like a customer success team, and recognizing the impact they have on revenue, that allows you to have a lot of really interesting marketing-driven touch points.”

A loan operates more like a SaaS contract than a one-time transaction, often running 6 to 18 months. The borrower’s decision to return for the next loan is earned or lost during that window, through every draw, every check-in, every moment the lender is either easy or hard to work with. Kendall views the servicing team as a partner to the revenue function because, in her model, they are.

The Handcrafted Bet Against AI Noise

Kendall uses AI to compress the analytical middle: the cohort analyses, the model building, the reporting. Tasks that once consumed weeks of a junior marketer’s time. Her approach to building teams follows what she calls a “first who, then what” philosophy, prioritizing curiosity as a leading indicator, including curiosity about AI itself.

She is also watching a pattern develop in lending, marketing, and building deliberately against it. “You start to sniff it out that content or posts are created by AI, and it hasn’t been totally edited,” she says. “Everybody’s kind of saying the same thing.”

Her term for the alternative is unpromptable. Marketing that could not have been generated by a prompt, because it required direct human observation, genuine customer insight, or a spontaneous act of generosity that no model would think to produce.

One example from her time at Upright: when investors closed with the company, the team sent handwritten notes with a cocktail (or mocktail) kit. “Thanks for taking a shot on us.” Assembled in the office, personalized by preference, nothing was asked in return. It was not designed to scale. That was the point.

In a space where lender messaging is nearly indistinguishable, she argues that the brands that earn repeat business are the ones that feel like they were made by someone paying attention. That standard does not come from a prompt. It comes from knowing your customer well enough to surprise them.

The Practitioner’s Edge

Across nearly a decade in real estate lending, Kendall has built the same engine multiple times: start with a clean audit, find out where the customer actually spends their day, then build for that reality rather than a theoretical one.

The channels, the product stories, the servicing touchpoints, the handwritten notes. These are the specific decisions of someone who has built this from scratch before and knows where the leverage lives. At Groundfloor Lending, she is doing it again.

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The Brand Beneath the Platform

Jess Wen does not separate brand from growth. After eight years and more than 150 venture-backed companies, she has stopped treating them as competing priorities.

“Brand is what people say about you when you’re not in the room,” she says. “It’s the sum total of all touch points.”

That definition sounds simple. The execution is not. For Jess, brand is not a logo refresh or a tagline. It is every product decision, every certification pursued, every member story told, and every moment a company chooses to act in accordance with what it says it believes. When a company does that consistently, over time, something measurable happens. Retention improves. Referrals increase. Word of mouth compounds.

That is the financial case for brand. And it is the operating thesis behind her work at SoLo Funds.

Meet Jess

Ask Jess about her ideal environment and she does not hesitate. A cozy room, a stack of books, a cup of hot tea, and what she calls her “fat lazy dog.” She is currently reading “The Anxious Generation” by Jonathan Haidt. She gamifies her personal life the way she structures her professional one: with deliberate quests. Last year, during a sabbatical in San Francisco, she set a goal of 100 new experiences in the city. She completed it.

When she returned to full-time work, she found herself slipping back into routine. So she set a new side quest: introduce deliberate newness into daily life and keep wandering down the small alleyways of a city she already knows well. “Continue to discover, continue to be curious,” she says. For Jess, that restlessness is not a personality quirk. It is a professional discipline.

She also teaches. Jess runs a creative entrepreneurship course for undergraduate design students, a 15-week class that, in her words, makes her a better operator. “Teaching actually makes me better at my day job,” she says. “I see the parallel of people leaning into the skills they have and immediately wanting to flex that skill set.” Watching students default to building before defining the problem taught her something she now applies every day at work.

From Client Service to In-House: Two Very Different Maps

Jess spent the majority of her career on the client service side, working as an outside consultant across a broad range of venture-backed companies spanning sectors and stages. She describes the work as pattern recognition at scale. “I’ve probably seen a version of every possible problem within venture-backed companies,” she says.

That breadth trained her well. The transition to an in-house leadership role, however, required a different kind of map.

In client service, brand strategy begins with a bird’s-eye view of the customer journey. The team identifies key touch points across awareness, consideration, and engagement, scopes the work, executes with precision, and exits. The time horizon is short. The brief defines the boundaries.

In-house, the exercise runs in the other direction. Jess starts with the annual business roadmap and reverse engineers into the touch points worth prioritizing. “What is reasonable, given resources and dependencies? What are the A, B, C we should focus on to improve brand and experience for Q1?” The horizon is longer. The constraints are internal. And unlike a client engagement, there is no clean exit.

“I want to run with B and C initiatives, but the dependency results in a lot of reality checks and rescoping,” she says. “Picking the battles, when wearing an in-house leadership hat, is about having my immediate function’s priorities and goals but also handling curveballs with grace and a collaborative spirit.”

The Patterns That Keep Repeating

After working with more than 150 venture-backed companies, Jess has catalogued a short list of brand failures that repeat across stages. Two stand out.

The first is what she calls the founder-as-brand trap. In the earliest days of a company, this is not a trap at all. It is necessary. Founders typically carry the charisma, the conviction, and the credibility. The brand and the person are inseparable by design. “Any entrepreneur who goes into a startup scenario usually has a certain charisma to really believe in what they’re building,” she says.

The problem arrives at the growth stage, when the company begins to scale and the founder cannot duplicate themselves five times over. If all of the brand equity has accumulated in a single person, the company has not built a brand. It has built a personal platform.

Jess uses an education metaphor to describe the transition. Early-stage companies are the grade schoolers. There are very few rules. The founder leads. But moving into the growth stage requires separating individual personal brand from company brand.

“The company brand needs to be strong enough and firm enough to stand on its own, without over-relying on the individual charisma.”

Her diagnostic question for founders who want to self-assess: when you walk into a conference and introduce yourself, do people think of your company name first, or do they think of you?

The second pattern is the “if we build it, they will come” assumption, most common among technical founders. Jess sees this clearly in the current AI funding environment, where some companies are getting away with skipping the story because capital is flowing fast. But she does not believe that lasts. “Those companies will not be the most stable ones going forward,” she says. The mirror image of that failure is the founder who sells aggressively before the product exists and then scrambles to build it after. Both profiles skip the same foundational question: what problem are we solving, and who actually cares?

She points to consumer brand companies as a model for tech founders to study. Omsom, a direct-to-consumer sauce brand co-founded by two Asian American sisters, earns her admiration not because of its size but because of its clarity. The company solved a specific problem: busy professionals who want to cook flavorful, internationally inspired meals without stocking dozens of bottles and knowing what to do with them. “They found their story early on,” she says. “They are solving a very clear problem that people care about.”

SoLo Funds: Humanity Inside a Financial Product

Jess first encountered SoLo Funds in 2020 as an outside consultant, brought in to lay the initial brand foundation for a peer-to-peer lending and borrowing platform still finding its language. She joined full time as Vice President of Brand and Growth in December 2025.

SoLo Funds operates as a community banking platform. Roughly 50 percent of American households live paycheck to paycheck, a figure the company tracks each year through its Cash Poor Report, produced in partnership with academic research institutions. When an unexpected expense hits, which it does, frequently, the traditional options are either a big bank or a predatory lender. SoLo offers a third path. The platform connects members who want to lend with members who need to borrow. Nearly three million members strong, the platform recorded close to 600,000 individual peer-to-peer transactions in 2025 alone. SoLo also holds the distinction of being the first and only B Corp certified lending company in the United States.

The brand work Jess began in 2020 had a clear brief: bring humanity into fintech. “Every messaging, visual, and brand touch point needed to really honor that,” she says. The founders, both Black, built the company from direct experience. They had been the person who needed to call a cousin or an aunt for help getting by. That sincerity, in Jess’s view, is not a marketing angle. It is the actual brand. “Over time, it’s not just a founder story,” she says. “It’s about actual member stories, people who are benefiting from our platform.”

The B Corp certification is a concrete example of how that belief system translates into a business decision. Going through the certification process requires significant resources and a rigorous accounting of social impact practices. The company chose to do it anyway. “The willingness to commit the resource to go through it backs the belief system,” Jess says. That commitment is brand. The certification is the proof.

Why Brand Matters More Now Than It Did Before

Jess makes a specific argument for why brand has become more important in the current environment, not less. Product parity is accelerating. With AI tools now available to most teams, shipping a clean, functional product is becoming closer to a baseline expectation.

“Consumer expects the product to work. Beyond that, whether or not it can speak to people, relate to people, connect to people, all of that is the importance of brand.”

She frames it bluntly. “Everything looks the same.” Consumers are fatigued. Attention spans have shortened. The volume of content, advertising, and product noise flooding any given channel has never been higher. In that environment, the companies that earn trust are the ones that stand for something clearly and demonstrate it repeatedly. Not through campaign flags. Through consistent behavior over time.

The analogy she draws is a useful one. Nike does not put a consumer’s name on an ad to earn business. Nike earns business by consistently aligning with aspiration through the athletes it chooses, the stories it tells, and the standard it sets for what the brand represents. That distinction, between brand audience and acquisition audience, matters.

“Brand should always feel a little more aspirational versus the acquisition audience who will actually use the product.”

AI, Personalization, and the Limits of Automation

SoLo Funds recently built and launched SoLo IQ, a proprietary AI-powered personal finance tool available to members within the platform. The motivation was observational. The team noticed members uploading personal bank statements into open-source AI tools to get budgeting advice. Recognizing a significant data risk, Solo developed a GLBA-compliant, secure, and encrypted alternative inside its own ecosystem.

The response was immediate and overwhelming. Between September 2024 and now, the platform recorded 74,428 unique IQ users against 68,290 unique borrowers—an adoption rate of 109%. This figure exceeds 100% because the tool’s value extends beyond active borrowers to members simply browsing the app or exploring features. It isn’t just a novelty, either: SoLo IQ maintains 94.65% uptime, averaging 23 conversations per hour, with 93.34% of those interactions delivering measurable value to the user. The product did not begin as a growth initiative; it began as a response to a real and specific human need.

The retention data tells an equally compelling story—and reinforces that brand is built across every touchpoint a member encounters, not just marketing campaigns. SoLo IQ users retained at 69.4%, compared to 60.6% for non-users, a lift of 8.8 percentage points. The more striking figure is on the lender side: IQ-enabled lenders retained at a rate 13.5 points higher than their non-IQ counterparts. Because lenders represent the supply side of the marketplace, that number carries outsized weight.

On the question of AI within her own team, Jess is measured. She references a Harvard Business Review article that found people are working more, not less, after introducing AI into their workflows. She sees that pattern in her own department. Every Thursday, her team holds a learning session dedicated entirely to sharing new AI workflows with each other, a structured attempt to raise collective literacy rather than assume everyone will figure it out independently.

Her framework for how AI changes the role of the marketer: AI is excellent at repeatable tasks and detailed research. Humans remain responsible for weaving those outputs into a coherent point of view. “I need the human intelligence to tell me the so what,” she says. Her goal is to move team members from straight-line execution toward a higher altitude, where the job is connecting dots and understanding the strategic reasoning behind the work.

"I need to elevate my team from a straight-line execution perspective to an airplane view. A higher altitude where you see a wider picture, connect the dots, and understand the strategic thinking behind why we are running all of these tasks in the first place."

She gave a talk to roughly 200 creatives in San Francisco two weeks before our conversation. Her call to action: continue to imagine, continue to grow in creativity, and continue to elevate your taste. Not just from good AI output to acceptable AI output, but from acceptable to genuinely great. “It’s not prompt it and forget it,” she says. “How do we continue pushing apart and moving forward?”

Looking Ahead

Jess is thinking about what comes after SoLo IQ. The next chapter, she describes as a “bit of a spoiler,” involves using AI analytics to tell a larger data story about everyday American spending habits and financial behavior. SoLo sits on a rich and growing proprietary data set from millions of members across diverse economic circumstances. The team is working toward surfacing that data in ways that reveal something true and specific about how ordinary households manage money, not to sell a product but to anchor a public narrative.

For a brand built on the premise that the financial system has underserved a significant portion of the population, that kind of data storytelling is not adjacent to the mission. It is the mission made visible.

“I think there is a lot of very rich story there. AI for real human needs that realistically benefit not just the top one percent, but a much wider population.”

As AI tools spread further into daily consumer behavior, Jess believes the most durable brands will be the ones doing exactly what SoLo has always done: starting with what is real, telling it clearly, and earning trust one touch point at a time.

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Isla Dickerson has a framework she uses before she touches a campaign brief. She does not start with key performance indicators. She does not open a channel dashboard. She starts with a question most marketing teams have set aside: what does this person actually feel right now?

As Head of Marketing at Happy Money, a consumer finance company that has helped more than 350,000 customers achieve their goals with a personal loan that provides a path out of credit card debt, Isla centers her operating philosophy around the gap between behavioral data and experiential truth. In her view, that gap is where most modern marketing falls short — and where the next generation of great brands will be built.

Meet Isla

Ask Isla about her ideal life and she does not hesitate. In the summer, she would run a bed and breakfast on an island off the coast of Maine, cooking lobster stew and strawberry rhubarb pie for interesting strangers, listening to their stories, and photographing the food for a cookbook she would write during winters in Hilo, on the quiet side of Hawaii’s Big Island. Every detail has a purpose. Every element earns its place. That instinct, to find what is true and what resonates, runs through everything she does at work.

From Community Banking to Fintech: What the Jump Actually Taught Her

Isla’s career began at a large independent credit card issuer, where volume was the currency and acquisition was the objective. After years at that scale, she founded an award-winning marketing and communications agency that never advertised, then returned home where she spent eight years leading marketing, community relations, and public relations at Bangor Savings Bank. Out of the blue, a former colleague called to say he had co-founded a startup and needed help. She left the structure of community banking for the disorientation of fintech.

What she found on the other side reframed how she thinks about the entire discipline. In a startup, product and marketing are not separate functions. They are often the same person making the same decisions.

“You are building a product while you are designing a marketing campaign and oftentimes you are doing that before the product is even fully built.”

She had to create marketing for an unfinished product while simultaneously marketing the organization, its people, structure, and potential, to multiple audiences. No historical data. No established playbooks. The friction was the education.

That experience sharpened a belief she now holds firmly: the best marketing thinking happens before the metrics arrive.

“Performance Ready” vs. Performance Marketing: A Framework for Building Backwards

Isla draws a distinction that sounds subtle but carries real consequences for how a team operates. She calls it the difference between performance marketing and being performance ready.

Performance marketing, as it has been practiced for the past two decades, starts from the back end. You define your target cost per acquisition. You set your click rate benchmarks. You design creative to pass an A/B test window. You optimize. The numbers tighten. And then, slowly, something else happens: the campaign converts in the moment but does not stick. The customer clicks and then leaves. The brand registers and then disappears.

“You’re optimizing yourself into this corner where everything converts in the moment, but it doesn’t resonate and it doesn’t stick.”

Performance ready is the opposing motion. You start with a human truth. What does this person fear? What are they hoping for? What would make them feel seen rather than targeted? You build from that place. You honor that truth in the creative before you touch the measurement framework.

“It’s not anti-data. It’s not dismissing the need for measurement. This is actually the more data-driven, rigorous approach.” Being performance ready multiplies what you measure and how you build. It expands the system beyond conversion to include sentiment shift, brand recall, referral, and long-term value, because you are no longer optimizing for the moment. You are designing for what makes performance sustainable. That requires deeper analysis, stronger synthesis, and tighter integration between data and human understanding. You are not just measuring what happens. You are designing for why it happens.

The campaign still gets measured. It just gets built differently.

Emotional Precision: The Operational Problem She Is Solving Right Now

Isla uses the phrase “emotional precision” to describe where she believes marketing is heading and where Happy Money is actively working towards.

She is not talking about putting a first name in a subject line. That, she says, is a playbook that was already aging before email existed. “We transferred the way that we wrote direct mail pieces into the email journey. Same content, different medium, no evolution.” What she is describing is harder to engineer: understanding not just what a customer did on your website, but why they did it, and what emotional state they were in when they arrived.

For Happy Money, this is not theoretical. Two visitors can land on the same debt consolidation page through the same search. One is on their lunch break, casually comparing rates. The other is at 2 a.m., having avoided their credit card statement for three weeks and living with constant financial anxiety. The action that got them to the site is identical. What they need from you at that moment is not.

One needs a nudge. The other needs reassurance. A single campaign version serves neither of them well.

Operationalizing this requires segmentation not just by behavior or demographic profile, but also by stage of readiness. Isla frames it as a binary: is this person in problem-awareness mode, or are they in immediate-action mode? That distinction shapes message, tone, creative direction, and offer structure.

The data needed to make these distinctions exists. The constraint has been speed: the inability to extract and act on contextual signals fast enough for them to be meaningful. That is the opening for AI.

Machines for Intelligence, Not Wisdom

AI handles the mechanical layer: A/B testing, bid optimization, content variations, reporting. It gets the middle steps done faster. What it cannot do is understand why a customer who just consolidated $30,000 in credit card debt might feel simultaneously relieved and ashamed. “It can’t feel the difference between a headline that’s clever and one that’s really true.”

“It’s machines for intelligence. It’s not machines for wisdom.”

The practical implication for her team is that AI accelerates the pipeline to insight. It surfaces patterns in data that used to take weeks to extract and makes them available in hours. That speed frees up human judgment to do the harder work: identifying the emotional truth, building the creative that honors it, and making the call on where to press and where to pull back. The skill that appreciates in value is not execution speed. It is human interpretation.

On agentic commerce, where AI agents locate and evaluate financial products on a customer’s behalf, she is measured rather than alarmed. “We are already heading down that path,” she says, drawing a direct parallel to the early days of Google search and the emergence of SEO. The search tools change. The underlying imperative: to be findable, credible, and emotionally resonant when the moment arrives, stays constant.

Credit Risk, Product, and Marketing

At Happy Money, Isla does not run marketing as a standalone function. Her closest operational partners are the credit risk team and the product team. She describes the three as pillars: none of them move without at least informing the others, and most significant decisions surface through all three before any action is taken.

The credit risk partnership is particularly concrete. Happy Money receives leads through affiliates, email, prior customer lists, and pre-screened direct mail channels. Every campaign Isla runs is shaped in dialogue with the credit risk team’s modeling. They inform her segmentation. They help build out personas. They review creative, not for compliance alone, but to ensure that the people being targeted with a given message are the people the model has identified as the right audience for that offer.

“Designing creative that blends and serves the segmentation that credit risk models out is an art.”

The result is a pre-screened direct mail process that operates as a precision instrument: response rates, approval rates, and risk-reward weighed together. Marketing and credit risk are not running separate plays. They are co-designing the same one.

Loyalty as Forgiveness: The Long Arc of Retention

The definition of loyalty Isla operates from now is less about repeat purchase and more about forgiveness.

“Repeat purchases are the baseline. Loyalty is resilient trust—the kind that holds when something goes wrong and the relationship endures. And it’s that trust, not behavior, that ultimately defines customer long-term value. If we’re not measuring it, we’re missing the signal that matters most.”

Her example is L.L. Bean, a brand she grew up with in Maine. When the company changed its longstanding return policy, one she had relied on personally, they explained the decision in a way that made sense to her. The relationship held. She still buys from them. She still recommends them. The brand had built enough trust that a broken promise did not break the relationship.

That is the standard she is building toward at Happy Money. Campaigns that convert are an imperative. Relationships that survive a mistake are the goal.

Looking Ahead: The Marketer as Psychologist

The marketing team of the future, as Isla envisions it, still operates as a performance engine, but one increasingly powered by AI and machine learning. Automation takes on execution and optimization, making the system faster, more precise, and more efficient.

Alongside it, a human data lab emerges. Fewer specialists focused on channel mechanics. More psychologists, storytellers, and community builders. More people with experience beyond marketing: those who have run businesses, worked in customer service, or developed a deeper understanding of human behavior, capable of directing machine output with judgment and applied wisdom.

“You can never outsource humans. We’re selling things to humans. We need human wisdom to do that effectively.”

The technical layer scales through automation. The human insight layer directs it and becomes the competitive advantage. The role of the CMO expands accordingly: still building and managing a demand generation engine, and now requiring an honest read of what customers feel and experience with the ability to translate that truth into inputs that guide the system, so what gets optimized is not just efficient, but meaningful.

Start with insight. Build for stickiness.

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