How Chapter achieved 10x revenue growth while keeping corporate headcount flat for 2 years

Cobi Gantz

CEO & Co-Founder

Bio

Cobi is the CEO of Chapter. Prior to Chapter, he led US government teams at Palantir Technologies, where he supported federal US government agencies on their most complex data challenges. He holds undergraduate degrees in Business Economics and History from the Wharton School and the University of Pennsylvania. He also received a Masters in Public Policy from the University of Cambridge, where he was a Thouron Scholar.

Cobi is the CEO of Chapter. Prior to Chapter, he led US government teams at…

Company:

Chapter

Location:

New York, New York, United States

Description:

Chapter was founded to ensure that every American preserves their health, wealth, and purpose in retirement. We started with Medicare, because good health is central to living a good life. Medicare is confusing and many bad actors profit from that confusion. We saw many of our own parents and grandparents being exploited and we decided to build a platform that put seniors first. Our advisors compare every plan nationwide, and recommend the best plan for each individual, regardless of whether or not we get paid. It’s the right thing to do and it’s what every American deserves.

Chapter was founded to ensure that every American preserves their health, wealth, and purpose in…

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Actionable
Takeaways

Execute government engagement yourself—consultants and lobbyists are value destruction:

Gantz cold-emailed high-level government officials and secured meetings directly, applying enterprise sales methodology to regulatory advocacy. The process mirrors complex deals: "navigating the bureaucracy, knowing whose motivations lie where, understanding overall prioritization...it can take months or years." His hard rule: "Do not spend a lot of time and money on consultants and lobbyists. That is quite obviously not going to work." The founder CEO is dramatically more effective than intermediaries because you control narrative crafting and bring authentic conviction. Prioritization matters in politics—even obvious policies don't pass without someone making them a priority.

Recognize when trust-building channels hit cost ceilings and pivot to trust networks:

Chapter launched with Gantz personally delivering Medicare education seminars at synagogues and churches—valuable for feedback and initial traction but clearly unscalable. When they tested direct-to-consumer ads, Gantz discovered seniors "inundated with a lot of ads, some scams, some not scams" made trust-building prohibitively expensive. He pivoted to enterprise partnerships with organizations that already held trust: health systems fielding Medicare questions they couldn't answer, wealth managers whose clients needed guidance, and later content creators with established audiences. The unlock was accessing existing trust infrastructure rather than building it customer-by-customer through paid ads.

Treat influencer partnerships as complex enterprise sales with unique power dynamics:

Chapter's influencer motion started accidentally through a Dave Ramsey introduction, then scaled after inbound from YouTubers. Gantz emphasized critical nuances: entry point matters intensely (going through talent versus agents/managers with misaligned economics), creators are "very skeptical, for good reason because most Medicare organizations are pretty slimy," and the relationship requires ongoing excellence because "they hear from their audience all the time." Structure deals as exclusive, long-term partnerships where you must deliver exceptional product experience. Create low-stakes testing frameworks where both sides can exit cleanly if fit isn't there. User referrals became Chapter's largest volume source—validating that product quality, not creator scale, drives sustainable results.

In industries with broken practices, hire zero people with domain experience:

Chapter has never hired anyone from healthcare or their specific distribution channels. Gantz's philosophy: "We look for very smart, hungry people who we think are good at their craft but have never done it in the industry we're doing it in. Because there aren't any great companies in this industry. So there's not really a talent pool to draw from." When the industry has systemic reputation problems and no excellent companies to source from, domain experience imports bad habits and limits imagination. Prioritize raw intelligence, hunger, and craft excellence in adjacent domains.

AI enables tech-enabled services to achieve better unit economics than traditional SaaS:

Chapter's corporate headcount stayed flat for two years during 10x revenue growth. Gantz observed that "LLM costs are not immaterial cogs so you have lower gross margin businesses in these LLM heavy companies. Tech enabled services and the best AI companies are actually converging to similar financial outcomes." The arbitrage: as software becomes easier to build, pure SaaS loses defensibility. Meanwhile, AI makes high-touch, premium experiences cost-efficient. Chapter now has "financials that look better than any SaaS company actually because we're so good at using AI." The lesson: resist proportional headcount scaling—most companies are "dramatically overstaffed" and "hiring more people often slows you down more than speeds you up."

Conversation
Highlights

How Chapter Scaled Medicare Navigation to 10x Revenue Growth While Keeping Headcount Flat

Most founders scaling tech-enabled services face a predictable trap: revenue grows, headcount grows proportionally, and unit economics compress. Chapter CEO Cobi Gantz broke this pattern entirely.

In a recent episode of Unicorn Builders, Cobi shared how Chapter achieved 10x revenue growth over two years while keeping corporate headcount “almost flat.” The secret wasn’t grinding harder—it was rethinking everything about how Medicare navigation companies operate, from customer acquisition to talent philosophy to the role of AI in operations.

From Senate Testimony to Strategic Pivot

Before Chapter became a Medicare navigation leader, Cobi found himself in an unusual position: testifying before the Senate about protecting seniors from predatory practices. The experience was “really nerve wracking,” and the preparation revealed critical insights about how policy and business intersect.

The testimony focused on ending a common industry practice where companies would sell senior data “to 100 or any number of third parties to call” after capturing lead form information. This created what Cobi described as “a lot of cold calls for seniors or perceived cold calls. It creates a really bad experience, and it reduces trust in the Internet writ large.”

Chapter successfully advocated for regulations requiring that lead form data only go to one party—the company displaying the form. But Cobi’s biggest learning wasn’t about policy mechanics. It was about founder-led government engagement.

“One of the most common mistakes I see founders make is they go spend a lot of money and time with consultants, with lobbyists and all these people who are selling to them,” Cobi explained. “And that is the biggest mistake. The reality is especially early, you have to do it yourself.”

His approach? Cold emailing government officials directly. “I’ve cold emailed pretty high level government officials and I’ve gotten meetings through cold emails which I think people just don’t even think to do,” he said. The key insight: treat government relations exactly like enterprise sales. “It often takes navigating the bureaucracy. It takes knowing whose motivations lie where. It takes understanding overall prioritization. It takes a lot of touch points. It can take months or years.”

The Synagogue-to-Enterprise Journey

Chapter’s go-to-market evolution reveals how sophisticated B2B distribution often starts with radically unscalable tactics. In the first year, Cobi personally delivered educational seminars at religious institutions. “The first year was me giving and a couple members of my team giving educational seminars at religious institutions, local synagogues, local churches, just saying, here’s how Medicare works. If you’re interested in talking to us, give us a call.”

It worked for building initial trust and gathering user feedback, but the limitation was obvious. As Cobi put it: “Wouldn’t scale to hundreds of millions of dollars of revenue, but it was pretty good to get started.”

The natural next step seemed obvious: direct-to-consumer advertising, the dominant channel for reaching seniors across television, direct mail, and Facebook. Chapter tested it and quickly discovered why trust doesn’t scale through paid ads in broken markets.

“We realized very quickly that it’s hard to build trust there because seniors are inundated with a lot of ads, some scams, some not scams,” Cobi explained. The problem wasn’t the channel—it was the cost of building trust when your industry has a reputation problem.

So Cobi pivoted to what he knew from Palantir: enterprise partnerships. Chapter began working with three types of organizations: health systems like Mount Sinai that field Medicare questions but can’t answer them due to regulatory constraints, wealth management firms whose clients need Medicare guidance, and content creators with established audience trust.

The insight was elegant: instead of building trust customer-by-customer through expensive advertising, access existing trust infrastructure.

Treating Influencers as Enterprise Deals

Chapter’s influencer strategy emerged accidentally. After an introduction to Dave Ramsey’s team, the channel started working. Then YouTubers began reaching out inbound, asking to partner because “they have a lot of people who ask them about Medicare because they talk about Medicare and Social Security.”

What makes Chapter’s approach different is how Cobi structures these relationships. “We really think about this like an enterprise sale. It’s not easy to convince these creators to work with us. They are very skeptical, again, for good reason because most Medicare organizations are pretty slimy.”

The deals are typically exclusive and long-term. Quality isn’t optional—it’s required. “They hear from their audience all the time, so they’ll hear good things. And if we mess up or if they have a bad experience, they’ll ask us,” Cobi noted. “So it is much more like an enterprise partnership where we have long term relationships, we’re usually exclusive and we have to do a really good job in terms of the product and the experience.”

The approach paid off. “This past year, it was really cool. For the first time, user referrals were our largest single source of volume, which are also unpaid,” Cobi shared. And of the paid partnerships, the economics are striking: “Only half of our enrollments are from paid partners. So the vast majority of our partners are unpaid.”

The Anti-Conventional Talent Philosophy

Chapter’s hiring strategy is deliberately contrarian. “We have never hired someone who’s ever worked in healthcare,” Cobi stated flatly. “We have never hired someone who’s ever worked in enterprise influencer sales.”

The logic is uncompromising: “We look for very smart, hungry people who we think are good at their craft but have never done it in the industry that we’re doing it in. Because there aren’t any great companies in this industry. So there’s not really a talent pool to draw from.”

When an entire industry has systemic reputation problems, domain experience becomes a liability. It imports bad habits and limits imagination. Better to hire exceptional people from adjacent domains and teach them the specifics.

AI-Powered Operational Leverage

The most counterintuitive aspect of Chapter’s growth is the headcount discipline. “For our corporate team, our headcount has been almost flat for 2 years as we’ve over 10x the company in terms of revenue,” Cobi revealed. “That’s because we hire really good people, we use really good technology and AI to grow.”

His philosophy challenges conventional scaling wisdom: “I think most companies are just dramatically overstaffed. You actually don’t need nearly as many people as you think. And hiring more people often slows you down more than speeds you up.”

This approach reflects a broader thesis about how tech-enabled services and AI companies are converging. “LLM costs are not immaterial cogs so you have lower gross margin businesses in these LLM heavy companies,” Cobi explained. “And so like tech enabled services and the best AI companies are actually converging to similar financial outcomes.”

The result? “Our financials look better than any SaaS company actually because we’re so good at using AI.”

Building the Trust Layer

Chapter’s long-term vision extends far beyond Medicare navigation. Cobi wants to “change the narrative of what it means to be older first in this country and then the Western world.”

The opportunity is demographic and technological. “People who are 65 today are actually quite young. They are going to have very long lifespans. They can use technology in different ways, but very capable ways, as you and I can,” Cobi observed.

Chapter’s strategy is sequential: establish trust through health and financial services first, then expand to help seniors “find purpose, find volunteer opportunities, figure out how to spend their time, how do they spend more meaningful time with their family and friends.”

Cobi calls this “the trust layer between seniors and AI.” It’s a positioning that acknowledges the fundamental challenge: technology adoption requires trust, and trust is exactly what seniors lack when navigating a predatory industry.

By solving Medicare navigation with exceptional product quality, building distribution through trusted partners, and maintaining operational discipline through aggressive AI deployment, Chapter is demonstrating a new playbook for tech-enabled services. The lesson for B2B founders: the best way to scale isn’t always adding headcount—sometimes it’s rethinking everything about how work gets done.

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