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Strategic Communications Advisory For Visionary Founders
Actionable
Takeaways
Test enterprise distribution earlier than your assumptions suggest:
Brian assumed Paytient needed a million users before insurers would engage. Instead, one of the nation's largest insurers partnered early because they recognized out-of-pocket costs as a critical experience gap they couldn't solve internally. The insurer's product team understood the problem but lacked control over member finances. When building in complex ecosystems, large strategic partners may engage earlier than expected if you solve a problem outside their core capabilities.
Prioritize partners with longer planning horizons:
Brian discovered insurers planning 2027-2029 health plans in early 2025, while employers focused on last month's challenges. This planning horizon difference fundamentally changed Paytient's GTM strategy. Insurers became the majority of their business because they could "invest and reshape for the long term" as part of broader strategy. When choosing between customer segments, prioritize buyers who think strategically over those managing tactical, short-term needs—they'll invest in solutions before acute pain points emerge.
Regulatory tailwinds can create massive distribution overnight:
A law passed four years after Paytient launched required all Medicare insurers to offer exactly what Paytient provides—prescription cost flexibility with insurer-fronted payments. This regulation instantly created a 50-million-person addressable market. Brian now powers this for "almost half the country." When building in regulated industries, track pending legislation that could mandate your solution category, creating instant distribution through compliance requirements.
Build different GTM engines for concentrated vs. fragmented markets:
Healthcare is "a very concentrated industry" at the top 40 insurers, where Paytient focuses enterprise efforts. For the fragmented small business market (under 200 employees), they launched a self-serve platform at patient.com this month, immediately gaining traction with venture-backed employers seeking simple subscriptions. The dual-motion approach—high-touch for concentrated markets, self-serve for long-tail—maximizes coverage without burning capital on inefficient sales motions.
In trust-based sales, delivery quality drives expansion velocity:
When Paytient launches with a Fortune 100, "tens of thousands of people have access to patient now." The benefits stack is "sacred and sacrosanct"—a trust-based, relationship-driven sale. Brian emphasizes the product must work "exactly how you said, even better" because performance creates referrals through benefit brokers and consultants. In high-stakes enterprise deployments, your product quality directly determines sales velocity through partner and customer networks.
Navigate regulatory constraints as creative boundaries, not barriers:
Brian's core advice for healthcare founders: "You have to work with the system as it is." Many founders approach healthcare "as antagonist" with solutions "too foreign or too different" that threaten the status quo. Instead, innovate within existing regulatory and operational frameworks. There are "plenty of space" and "data requirements for how healthcare can work today" to build billion-dollar businesses while respecting industry structure. Fighting the system guarantees slow adoption; working within it enables scale.
Conversation
Highlights
The Insurance Pivot: How Paytient Discovered Their Real Buyer Had a 3-Year Planning Horizon
Brian Whorley assumed he’d need a million users before any major health insurer would return his calls. He was building Paytient to solve healthcare’s payment problem—enabling patients to pay for care over time without interest—and the logical path seemed obvious: sell to employers for five to ten years, build massive scale, then approach insurers.
Six months in, one of the nation’s largest insurers reached out. His entire go-to-market thesis was wrong.
In a recent episode of BUILDERS, Brian, Founder and CEO of Paytient, explained how misunderstanding his real buyer nearly cost him years of growth—and how a Medicare regulation passed four years after founding created a 50-million-person addressable market his company now dominates.
The Scale Assumption That Almost Derailed Everything
Brian identified healthcare’s structural flaw clearly: “For decades, you have not been considered a consumer. Even in some health systems, that word has been a dirty word.” Patients lacked financial agency to transact. Providers had atrophied muscles for setting transparent cash prices. The entire buy-side and sell-side dynamic that defines functional markets simply didn’t exist.
Paytient’s solution: employers and insurers front out-of-pocket healthcare costs. Members get care immediately, then repay over time with zero interest. It eliminated the need for thousands of dollars in the bank at the moment of care.
But Brian made a critical GTM error. He assumed insurers—the strategic, long-term buyers—would only engage after he’d proven massive employer traction. “I thought I would need to sell to like a million people. Like I thought I needed to sell to thousands of employers and have a million lives on platform before a health insurer would pick up the phone and start working with us.”
This assumption locked him into a bottom-up employer sales motion: founder-led outreach to his network, one small employer at a time, grinding toward some theoretical scale threshold.
What the Early Insurance Partnership Revealed
When a top-three national insurer engaged early, the conversation exposed something Brian had completely misread about buyer motivation.
The insurer’s product team already understood the problem with granular precision. “They were like, hey, we know the out of pocket is like the worst part of the experience. It’s the shittiest part of healthcare,” Brian recalls. “We’re not unaware of that. It’s just the out of pocket’s out of our reach. That’s the Member’s responsibility, not ours.”
The insight: insurers couldn’t control member bank balances or income. They had zero leverage over the financial friction that directly impacted care decisions and member satisfaction. They needed an external solution to a problem they’d already diagnosed but couldn’t solve with internal capabilities.
Brian discovered “actually stronger, more resonant product market fit with health insurers much earlier in the journey” than his business plan contemplated. This wasn’t just about accelerated timeline—it fundamentally restructured who Paytient sold to and how they positioned value.
The Planning Horizon Gap That Changed Everything
The real differentiator between employers and insurers wasn’t company size or budget—it was temporal orientation.
“There’s health insurers today that we are working with literally today, like this morning, talking about what health plans will look like and function like in 2027, 2028, 2029,” Brian explains. These weren’t quarterly planning cycles or annual renewals. Insurers were architecting multi-year product strategies and capital allocation.
Contrast that with employer buying behavior: “I had an employer conversation earlier this morning. They’re just trying to figure out, hey, it’s January 23rd. Like we’re trying to figure out last month, this month.”
This planning horizon gap has direct GTM implications. Insurers think in terms of “lower cost plans” and “increased access for their employees” as strategic positioning—they’re willing to invest before acute pain points emerge. Employers operate in crisis mode, solving immediate problems with limited bandwidth for strategic infrastructure investments.
Health insurance companies now constitute the majority of Paytient’s revenue. The company focuses on the top 40 insurers—a function of industry concentration where “that’s a place where there’s incredible expansion and you have incredible impact and ability to deploy product at scale.”
How Medicare Regulations Created Mandatory Distribution
Four years after founding, a law passed requiring Medicare insurers to offer prescription payment flexibility—the exact capability Paytient had built.
The mechanism: beneficiaries walk into pharmacies, get prescriptions, walk out. The insurer fronts the copay and deductible in full. Members receive a month-end statement and repay the insurer—either in full or over time at zero cost.
“Fifty million Americans have a health insurance plan where they’re able to walk into a pharmacy and their health insurer actually pays the pharmacy their copay deductible on their behalf,” Brian explains. Paytient now powers this for “almost half the country.”
The regulation didn’t just validate product-market fit—it mandated distribution. Every Medicare insurer had to provide this capability. Paytient went from selling a nice-to-have to fulfilling a compliance requirement across 50 million lives.
This positioned Brian to testify before the House Committee of Oversight and Government Reform on December 10th as an expert witness on healthcare affordability. He represented “the voice of the millions of people that we represent, the voices of the 6,000 employers we work with” directly to policymakers shaping future healthcare legislation.
Dual GTM Engines for Concentrated vs. Fragmented Markets
Despite the insurance pivot, Brian didn’t abandon employers—he segmented GTM by market structure.
For the top 40 insurers: high-touch enterprise sales with multi-year deal cycles. These are strategic partnerships where insurers integrate Paytient into core benefit design, affecting millions of members.
For employers under 200 employees: self-serve at patient.com, launched this month. “If you’re a small business, less than 200 employees, you can go to patient.com and actually buy patient online now.” The MVP immediately gained traction with “venture backed employers who are like hey, I want to do something for my employees and they just want a simple subscription.”
The dual-engine strategy solves unit economics. You can’t profitably run enterprise sales for 50-employee companies. You can’t efficiently serve thousands of SMBs with strategic account management. Different market structures demand different acquisition and servicing models.
This approach enabled Paytient to close multiple Fortune 100 accounts last year—companies where “tens of thousands of people at those employers have access to patient now” at launch. When you deploy at that scale, product delivery becomes your sales engine. “The benefits stack is sacred and sacrosanct. It’s a trust based and relationship based sale,” Brian emphasizes. Performance drives expansion and broker referrals.
The Constraint: Healthcare’s Regulatory and Trust Infrastructure
Brian’s core GTM lesson for healthcare founders: “You have to work with the system as it is.”
The failure pattern he sees repeatedly: “Folks will kind of come at the system sort of as antagonist and come at it with something that’s sort of foreign, that maybe works against how it is today, that’s just almost too foreign or too different or that threatens the status quo in a way that it just won’t pull you in.”
Healthcare operates within regulatory constraints around data handling, compliance, and established workflows. The benefits stack is relationship-driven—HR teams trust specific brokers, consultants have established networks, decisions involve credit committees and multi-stakeholder approval.
“There are regulatory requirements for how healthcare can work today and so you have to sort of be considerate of the data and the way it can work,” Brian notes. “The art is innovating within those constraints but there’s plenty of space in there.”
His advice isn’t about compromising on innovation—it’s about understanding that healthcare’s regulatory and trust infrastructure creates boundaries that determine what’s adoptable. “There’s plenty of space for a lot of people to do a lot of good and build successful multi billion dollar businesses” within those constraints.
The lesson from Paytient’s journey: your initial GTM assumptions about buyer scale requirements, planning horizons, and market structure may be fundamentally wrong. Brian’s willingness to pivot from employers to insurers when he discovered stronger product-market fit—and then build differentiated GTM motions for each segment—enabled Paytient to serve 6,000 employers and power payments for nearly half of Medicare’s 50 million beneficiaries. Sometimes the market signals a better strategy than the one you planned, but only if you’re paying attention.
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