Jen Rapp's marketing education began with chalked hands. She was a rock climber first, then a college copywriter for Black Diamond Equipment, a company whose customers could tell when the person writing about an ascent had never left the parking lot. The job rewarded fluency before polish. Rapp knew the culture, talked her way into the work and discovered that participation can be its own credential.
That origin remains unusually useful. The modern executive biography often begins in a consulting firm or a rotation program. Rapp's begins inside a subculture with its own equipment, ethics, heroes and unforgiving definition of authenticity. Her route since then has crossed consumer brands, delivery technology, baby products, marketing software and creative services. The surface changed. The task underneath did not: understand what people hope to become, then make the business feel relevant to that hope.
A route drawn across three operating worlds
The long pitchPatagonia taught her to sell the summit, not merely the jacket
After Black Diamond, Rapp spent roughly a decade at Patagonia. Longevity is an unfashionable line on a technology résumé, but this one reads like an apprenticeship. She learned how a company could tell stories the public might not yet be ready to hear, and how mission could shape communications rather than decorate them. By 2010, she was Patagonia's director of communications and public relations. She later described the company as the place where she learned storytelling and brand building.
The outdoor industry also gave her a durable picture of aspiration. The climber shown on the side of Everest is not necessarily the buyer. A person walking through New York may purchase the jacket because it carries a fragment of the imagined life. Rapp would later apply the same logic to software and services. The scenery changes from a mountain face to an overworked marketing department, but the emotional mechanism survives. A product matters because of the problem it solves and the person it lets the customer picture becoming.
“You're still selling to that human being.”Jen Rapp on carrying emotional storytelling into B2B
Roles at TOMS and Arc'teryx kept her near products with identities larger than their specifications. Then she faced a fork. The obvious path led toward another outdoor brand. Recruiters, however, kept calling from technology companies. Rapp grew up around Silicon Valley and engineers - her father worked as a NASA engineer, and her mother was an engineer too - yet she once regarded the outdoor world as the more compelling one. Curiosity won. She crossed over.
A new kind of exposureDoorDash put the brand under a performance microscope
DoorDash was not yet the household name it would become when Rapp took a senior marketing role. The job introduced a different altitude. Data arrived quickly, channels could be inspected, and the effect of an idea could be argued in numbers. The brand work still mattered, but now it worked in public beside acquisition costs, conversion rates and a marketplace growing in real time.
This was the hinge in her career. Outdoor marketing had trained the right brain: image, identity, community, aspiration. DoorDash demanded the left: analytics, performance and the daily accounting of whether the story moved anyone to act. Rapp did not abandon one for the other. She became interested in the seam.
At Owlet, she served as Chief Brand Officer. At Klaviyo, beginning in 2021, she led brand and communications through a period that culminated in the company's September 2023 debut on the New York Stock Exchange. She marked the occasion with an object from her other life: vintage Chouinard Equipment pitons pulled from a big-wall rack. Klaviyo's name was inspired by a word for the climbing hardware. To Rapp, the worn metal represented a difficult ascent and the team required to make it.
It was an executive's metaphor, but it was also a copywriter's prop. An IPO can dissolve into abstractions about journeys and milestones. A scarred piece of protection brings weight, history and danger into the hand. Rapp wrote that her Klaviyo years had felt like one of the biggest climbs of her life. The pitons made the sentence visible.
The customer enters firstSuperside hired someone who had already bought the service
Rapp joined Superside as Chief Marketing Officer in 2024 with an advantage that no onboarding deck could supply: she had been a customer. She knew the buyer's predicament. In-house creative teams held ambitious briefs and finite hours. Every department could label its request urgent. The work backed up, the most capable people became production bottlenecks, and the large ideas lost oxygen to a queue of necessary assets.
A Superside study of 206 creative leaders gave the predicament a numerical outline. Seventy-eight percent said their teams felt burned out. Fifty-five percent of incoming requests were marked urgent. Rapp's response has been operational rather than romantic. Prioritize by impact. Use outside partners differently. Give internal talent room for the distinctive work. Test AI where it can speed briefs, storyboards, first drafts, localization and variation.
Her AI case is emphatic but conditional. A tool can multiply the ability of a trained creative; it does not supply taste to an untrained operator. Superside experimented away from client work before bringing new methods into production. Human creatives improved the first drafts. Customers could opt out. The criterion was not novelty. The criterion was whether a workflow saved time, improved quality or helped work perform.
“Today, what is judged as a good creative is a creative that performs.”Jen Rapp on connecting craft to an observable result
The company becomes the case studySix months to rebuild a brand from the inside
Superside's 2025 rebrand joined the pieces of Rapp's résumé in a single assignment. The company had grown into enterprise work, while its identity still described an earlier version of itself. Instead of hiring an outside agency, the team used its own service and completed the project in six months. AI assisted with ideation and production. Human designers defined and refined the system.
A Cape Town photo shoot supplied a particularly tidy example. The team photographed its astronaut mascot, trained a brand model on the original imagery and used it to generate consistent variations for future campaigns. One shoot could produce a longer runway. The savings bought experimentation, not an excuse to remove the people who knew what the brand should feel like.
The work also generated a small, useful failure. While the team concentrated on the new brand, its usual flow of fresh paid creative slowed. Pipeline dipped. They checked channels, targeting and campaigns before someone identified ad fatigue. The team released new ads with updated calls to action. Rapp said performance began to return within a day.
This episode is the practical spine behind her most repeated line: “Creative is the new targeting.” Advertising platforms and their targeting machinery are broadly available. When competitors can rent similar distribution, the visible work becomes a decisive variable. Her claim is not that data has vanished. It is that optimization cannot rescue an exhausted idea forever.
A broader briefFrom marketing the promise to owning more of the experience
By 2026, Superside's current leadership page listed Rapp as Chief Customer Officer. She described a remit touching more than 650 creatives, marketers, commercial leaders, operators, recruiters and talent managers. The change makes narrative sense. A marketer who entered as a former customer now carries responsibility closer to what customers receive. Josh Mendelsohn, Superside's vice president of marketing, appears alongside her on the leadership team.
On a May 2026 podcast, Rapp described an “agentic front end”: AI helps customers build a context-rich brief from previous brand information before a human team carries the work forward. The idea extends the rebrand's logic into the service itself. Machines can gather memory and reduce repetitive alignment. People remain accountable for the finish.
Her public life still carries the climbing world with it. Rapp is an active climber, mountaineer, skier, skydiver, paraglider and Cessna pilot. In 2026 she appeared as a former Patagonia publicist in The Dark Wizard, a four-part documentary series about climber Dean Potter. It is a rare executive biography in which an HBO documentary credit and a B2B pipeline lesson occupy adjacent years, but the proximity feels honest. Both concern risk, judgment, teams and the stories people tell about difficult routes.
Rapp's career offers no promise that every creative problem has a clever technological answer. It offers a more durable operating habit: go close to the culture, learn its language, measure the result and keep the skilled human near the controls. The climber became a copywriter because she knew the terrain. The copywriter became an executive by learning new kinds of terrain without pretending they were the same.
Now the terrain is crowded with models, agents and tools that appear faster than most teams can absorb them. Rapp's response is to experiment, train and remain optimistic, while asking the severe old question of performance: did the work do what it came here to do? It is the sort of question a climber might respect. The view matters. So does the route.