Building healthcare technology is hard. Bringing it to market is harder. We’ve spent the past 3 years interviewing healthcare founders and operators to unpack their GTM journeys: earning trust in risk-averse buying committees, navigating multi-stakeholder economics across payers, providers, and patients, proving clinical credibility through evidence, shortening long sales cycles with partners, and scaling adoption inside complex institutions without breaking workflows. The 46 founders featured here have built and scaled across digital health, medtech, payer services, pharma, AI, and provider operations. Here are 46 lessons from their go-to-market journeys.
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GTM Lessons
Arif Nathoo
CEO & Co-Founder of Komodo Health
Product Evangelism Beats Enterprise Sales Playbooks
Arif built Komodo’s enterprise growth engine by creating evangelists inside large organizations rather than relying on traditional sales motions. “We have folks within these large enterprise healthcare companies that love Komodo. They go to bat for Komodo, they speak about Komodo, and they evangelize us in their own companies.” These internal champions came from marketing teams using the software to understand patient journeys, then told colleagues in analytics and IT about specific outcomes. “When somebody on the marketing team that’s using Komodo software to deeply understand the journey of a patient is then telling their colleagues and analytics, it’s telling their It team, it’s telling their manager that we use Komodo to actually identify this unmet need.” Arif described the underlying principle bluntly: “it’s really not great products that win, it’s just less sucky products that win.” But evangelism created the right to have the next conversation and push the next sale. “The evangelism around your product allows you to have the right to have the next conversation, to push the next sale.”
Gregory Stein
Founder of Shadowbox
Credible Partners Unlock Risk-Averse Enterprise Buyers
Gregory built Shadowbox’s healthcare GTM around partner credibility as the primary door-opener in a notoriously slow-moving industry. “Getting your foot in the door with a credible partner as a reference is probably the most important thing in healthcare. Healthcare is one of the slowest to adopt industries out there.” He structured partnerships in layers, starting with vendors selling to the same customers (RCM vendors, lab information systems) before moving to larger strategic partnerships. The HC1 partnership exemplified this strategy: “The credibility that having a much larger partner like HC1 as our partner brings to the Shadowbox technology” opened access to their customers “in a way that is scalable and helpful for both our partner and for us because it improves their own relationships to bring our services.” In risk-averse markets, the partner’s credibility became more valuable than product features in shortening sales cycles.
Teodor Grantcharov
Founder of Surgical Safety Technologies
Win the Hardest Customers First to Prove Category Value
Teodor built Surgical Safety Technologies’ credibility by deliberately targeting the most challenging buyers instead of easier early wins. “We had a very clear hypothesis of who we saw as customers or the right customers in the early stage. And our hypothesis was, let’s shoot for the most challenging customers. Let’s shoot for the top hospitals in the United States, top hospitals in Canada, and the largest academic centers in Western Europe.” These institutions had sophisticated internal systems and knowledgeable professionals, creating a high bar. “In order to succeed there, you need to meet a very high bar. But we said, okay, let’s take this challenge early on, and if we can make the best in the world even better than we can make anyone better.” Landing top academic centers as early adopters created proof points that made selling to everyone else significantly easier, turning demanding customers into category validators.
Mike Desjadon
Chief Executive Officer of Anomaly
Anchor Deep Before Scaling Sales in Long-Cycle Markets
Mike rejected what he called “annual curiosity revenue” – customers trying AI products for a year with easy exits – and instead built Anomaly’s entire capital structure around deep relationships with 1-6 anchor customers. “We wanted was a much smaller amount of very deep relationships. Like even if it was just one customer, we wanted to be sticky as all get out because in this space it’s rare that it’s like one you’re never going to get somebody on a pitch of like oh you have screen X, we have screen X plus whatever.” With 14-month sales cycles, he focused on “individual customer growth” by forward-deploying engineers and prioritizing customer success over premature sales hiring. “What is the smartest thing we can do as a company…to get a real customer that we’re going to live and grow with, that we’re not going to churn out of, to really show unimpeachable value, to make that front end sales conversation two years from now significantly easier.” The strategy worked because healthcare buyers needed case studies, not investor brands: “show me the six organizations that I know that you work with that are going to tell me I should work with you.”
Nabeel Kaukab
Founder & CEO of Phamily
Solve Provider Economics First, Patient Outcomes Second
Nabeel learned that leading with patient benefit messaging killed deals in healthcare because providers already felt maxed out on unpaid care. “Coming into a doctor’s office and saying you need to do the following for your patients or your patients deserve this. That is not going to go well.” Doctors responded: “I’ve been taking care of people by paying out of my own pocket. And I can’t afford to do any more than I already am.” He repositioned Jaan Health around provider economics instead: improving reimbursement qualification, expanding care capacity, and fixing workflow. “If you can’t fix the economics of their business, you are dead on the run…doesn’t matter about anything else you do.” This economics-first approach enabled Jaan to build an eight-figure ARR business without discounting: “We sold value. We created value for our clients, created value for their patients and then created value for ourselves.”
Cody Simmons
Co-Founder & CEO of DermaSensor, Inc.
Turn Clinical Publications Into Self-Service Sales Collateral
Cody built Dermasensor’s private practice sales motion around published clinical validation that allowed physicians to verify claims independently without sales involvement. “We have seven published studies and two of them specifically showed that the device is as accurate as in person dermatologist assessments for a given suspicious lesion.” This academic validation replaced traditional enterprise sales proof points and accelerated private practice adoption. “Many studies and publications we’ve seen really fast kind of uptake, especially private practices” because doctors could evaluate clinical validity themselves before purchase conversations. Publications functioned as automated credibility builders that enabled “hundreds of private practices have already come on board. Just a year” – the studies did the technical selling while the sales team handled logistics and implementation.
Veer Gidwaney
CEO and Founder of Ansel Health
Turn Incumbents Into Distribution Partners With Platform Model
Veer built Ansel’s GTM around a platform model where incumbent insurance companies ran white-labeled versions of Ansel’s product on Ansel’s infrastructure. “We came up with this model where we would use the platform that we built to power other insurance companies to bring their own versions of Ansel to market” – partners took on the risk and used their own brand while Ansel provided the technology. Early strategy was to “form a coalition of companies that can help us accomplish this goal together” rather than compete head-to-head. “That go to Market Motion has allowed us to gain the credibility of those brands, to gain the access to their own distribution channels because they’ve been around much longer than we have, much more strong and broad than we could do on our own.” The partnership model let Ansel scale through established distribution while incumbents got a superior product they couldn’t build themselves.
Thomas Knox
Founder & CEO of VitVio
Recruit Top Clinicians As Advisors To Unlock Hospital Access
Thomas cracked hospital access by recruiting leading surgeons as advisors instead of cold-calling executives who ignore vendor outreach. “Go on LinkedIn, find the top surgeons at certain hospitals and say, hey, I want to talk to you and show you what I’m thinking and I want to get your opinion.” Surgeons “don’t get in as many of these” pitches compared to administrators, making them more responsive. The tactic worked because “no hospital on the planet will reject a meeting with their top surgeon” – advisors became door-openers rather than just product validators. “If you go and you try to reach out to like a hospital executive, they’re going to tell you from the outset, no, I don’t want to talk. Or they won’t even respond.” VitVio used surgeon advisors as “leverage to open the door in the first place” by having them request meetings executives couldn’t refuse.
Trey Sutten
Chief Executive Officer of Siftwell
Sell Business Outcomes, Not Technical Accuracy Metrics
Trey rejected the technical positioning common among healthcare AI vendors and instead positioned Siftwell on business outcomes operators actually cared about. “I think a lot of technologists have entered the healthcare industry and thought that…it was a better model, a better mousetrap…They wanted to talk about accuracy measures like area under the curve” – metrics that meant nothing to buyers. His operator experience revealed what actually mattered: “This isn’t about how accurate your model is, it’s about your model telling me that an individual needs an intervention and so that their use of an emergency department or their readmission rates go down.” He framed this as a former operator perspective: “What way more important to me is getting the results that I’m trying to get.” Siftwell sold on reducing ER visits and readmissions, not on model performance – a positioning shift that came from understanding the buyer’s actual job.
Torben Nielsen
CEO and Co-Founder of Uptiv Health
Target Awareness Gap, Not Direct Competitors
Torben focused Uptiv’s GTM on category education rather than competitive differentiation because most buyers didn’t know retail infusion centers existed. “There’s still a lot of specialists and a lot of patients that don’t necessarily know about the retail based model that we are providing at Uptiv. And so getting awareness out is really key.” Instead of attacking hospitals as competitors, he positioned them as potential partners facing capacity constraints: hospitals posed “a threat or an opportunity to partner” depending on how Uptiv approached the conversation. The primary competitor wasn’t other ambulatory infusion centers but rather market ignorance – specialists and patients defaulting to hospital-based infusion because they didn’t know alternatives existed. Uptiv’s sales motion prioritized educating the market that retail infusion was possible over explaining why Uptiv was better than other retail options.
Ignacio H. Medrano
Founder of Savana
Build Scientific Credibility Before Commercial Traction
Ignacio prioritized peer-reviewed publication over commercial scale because academic validation mattered more than revenue in healthcare markets. Savana generated first revenue “less than one year” after launch, proving commercial viability quickly. But “it took us more time to convince the journals, the scientific journals that they could publish what we’re doing. That took us three, four years” – scientific validation took 3-4x longer than getting paying customers. Journal publications became the critical credibility signal that enabled mainstream adoption beyond early innovators. Academic acceptance through peer review preceded and enabled mass market commercial traction, not the other way around. Ignacio invested in the longer, harder path of scientific validation knowing it was the unlock for category credibility in a market where clinical evidence trumped customer logos.
Amar Kendale
President and Co-Founder of Homeward
Design For All Three Stakeholders: Patient, Provider, And Payer
Amar designed Homeward’s product for the entire healthcare ecosystem because “you can’t afford to neglect anyone because that’s going to be your Achilles heel.” Each stakeholder could kill the GTM motion independently: “If you focus on the patient and the provider, you leave out the payer and you may not get paid. And if you focus on the patient and the payer and you leave out the provider, well, you may never get prescribed and you may never show up in the provided workflow.” Multi-stakeholder design created unexpected benefits beyond market access – it built a defensive moat because competitors couldn’t easily copy the complexity. “Ankle biters…doesn’t show up very often in healthcare…the fast followers” struggle to replicate solutions designed for multiple stakeholders simultaneously. The added complexity scared off competitors while solidifying Homeward’s market position.
Rafid Fadul
Co-Founder / CEO of Zivian Health
Start With The Beachhead That Unlocks The Market
Rafid chose compliance as Zivian’s entry point because it was “so messy” and “not core to any practitioner’s practice, but it poses an existential risk to everyone.” The beauty of this beachhead was that it created urgency without requiring behavior change—practitioners needed this whether they wanted it or not. Compliance wasn’t sexy, but it was mandatory: “if you don’t do this right, you remember in high school or in elementary school they said, oh, if you don’t do this, it’s going to go on your permanent record. So I didn’t know this, but doctors actually have that.” By solving a problem that was both high-stakes and highly fragmented across state regulations, Zivian built a wedge that made the sale inevitable rather than aspirational. The practitioners weren’t choosing between solutions—they were choosing between Zivian and existential professional risk.
Mark Lehmkuhle
CEO & CTO of Epitel
Ignore Early-Stage VC Advice When Your Product Timeline Doesn't Match Their Fund
Mark received “a lot of bad advice of, oh, you should go through kind of seed investors, seed stage investors, when really our NIH grants were that seed stage for us.” He wanted to raise $20M but advisors pushed him toward $1.5M-$2M seed rounds that made no sense for a regulated medtech product. The core issue was timeline mismatch: “any seed stage investor is just not going to see the return on that investment for a long period of time.” Instead, Mark skipped seed entirely and went straight to Series A investors who “know what it takes to develop a medical device, and they’re in it for the long haul.” For products with regulatory timelines, matching your fundraising stage to investor patience mattered more than following conventional fundraising sequencing.
Kristen Valdes
Founder and CEO of b.well Connected Health
Show Analyst Firms Consistent RFP Patterns to Trigger Category Creation
When Forrester initially pushed back asking “where do you fit?” Kristen had to prove market demand through buying behavior, not vendor positioning. She demonstrated “there are now RFPs that are specifically designed around this rearchitecture, around interoperability, around having access to a longitudinal health record” to show the category was real. The analysts needed evidence that “there’s intentional buying and you see the same sets of people over and over again in these categories” before they’d create the classification. Kristen’s approach worked because she understood “a vendor is not going to create a category, not in healthcare. It has to be the buyers saying I have budget and I am putting money aside for this pain point.” The category materialized almost ten years in once consultants consistently wrote similar requirements and the same vendors appeared across multiple RFPs.
Nick Soman
Founder and CEO of Decent
Find A Movement Bigger Than Your Company And Become The Arms Dealer
Nick realized direct primary care wasn’t just a product feature—it was “a true movement” of 8,000 clinicians who had “realized after working their whole lives to be able to do this special thing, that they took real serious to take care of people, that their job had been perverted.” Instead of creating his own movement, he positioned Decent as “the arms dealer to this movement” by solving DPCs’ distribution problem: bringing them employer members. His pitch became devastatingly simple: “we bring you members, you take care of them, we pay your rack rate” with a 95%+ close rate. Nick explicitly prioritized movement growth over company growth: “I am much more interested at this moment in supporting the growth of direct primary care than even supporting the growth of decent, because I know the good things that will happen for decent if we can be in service to this movement.” The movement’s momentum became Decent’s distribution engine—DPC doctors lined up at their booth because “we brought their friend members.”
Avi Singer
CEO/Founder of Showd.me
Don't Create Demand—Position As The Partner Who Understands Why Previous Solutions Failed
Rather than competing on features in a crowded compliance market, Avi positioned Showd.me around demonstrating deep understanding of past failures: “we’re not just coming and saying, hey, we sell online compliance training, but really come in and say, we understand why this has not worked for you before. We understand why you’re hesitant to move from classroom to online.” His sales approach centered on proving domain expertise: “we understand the market, we understand the users. We understand what you’re trying to do. We understand your business, and then we want to partner with you.” This converted prospects because “when that comes across as authentic” they realized “this isn’t somebody just trying to sell me a product. This is somebody who’s taken the time to understand what our business challenges are.” The positioning worked because compliance training demand already existed—Avi didn’t need to create it, just capture it by addressing why buyers had rejected previous vendors.
Elad Ferber
CEO of Synthpop
Sell Labor Replacement, Not Software, To Change Budget Category And Buying Behavior
Elad repositioned Synthpop entirely outside traditional SaaS sales by declaring “we don’t sell software, we sell labor. It’s not the same category of expense for our customers, because when you delegate a task to one of our agents, you don’t need to do it, and you don’t need to do it anymore.” This wasn’t just messaging—the pricing model enforced it: tasks like calling payers and navigating phone trees for an hour were fully automated, and “if we miss even one thing…we don’t charge our customer at all.” By framing the product as labor replacement rather than software, Synthpop changed both the budget line item and buyer psychology: customers treated agents “like an employee or like a contractor” that “saves real work” rather than evaluating it as “a SaaS product per se.” This positioning unlocked faster adoption because it competed against staffing costs, not software budgets, and eliminated the need for customers to change their existing workflows or systems of record.
Justin Dearborn
CEO of Praia Health
Position As Platform That Accelerates Existing Investments, Not Replacement Technology
Rather than forcing health systems to rip out existing patient engagement and digital front door investments, Justin positioned Praia as the integration layer that made those sunk costs more valuable: “a platform that’s going to make all those investments that have happened in patient engagement, digital front doors, and make those more beneficial to the health system and the patients consumers using them.” The core value proposition centered on time compression for IT teams: “a health system might take six months to enable a use case under traditional methods that you’re integrating with the EMR” but “once PRIA is implemented that can be down to a couple days because we’ve already done that heavy lifting, integration and synchronization with the electronic medical record or the CRM.” This “better together” positioning unlocked channel partnerships with companies that had “a decent established footprint” by enhancing rather than replacing their solutions. The strategy worked because health systems didn’t have to defend past purchasing decisions or battle internal politics—Praia made existing investments perform better, which turned IT from potential blockers into advocates who could “plug into” the platform for faster implementation.
Dimitrios Skaltsas
Co-Founder & CEO of Intelligencia AI
Target Forward-Looking Functions Within Conservative Industries For Early Adoption
In pharma, which Dimitrios acknowledged was “a conservative industry, for all good reason” due to regulation and patient safety, he found his entry wedge not in core R&D but in innovation-mandated functions. His first customer was “a major pharmaceutical company” that had built “this external innovation function where they look for new drugs from smaller companies, from biotech, and by default, they were building something that was forward looking and they want to embed innovate elements.” These teams were “the perfect match” because their organizational mandate required adopting new approaches, unlike traditional pharma functions where “the innovation propensity” for technology was “unfortunately a bit backwards.” By targeting functions explicitly chartered to experiment with emerging tech, Intelligencia avoided the “moneyball moment” friction of selling data-driven decision making to an industry that hadn’t yet adopted it broadly. This strategy let them prove the technology with early adopters who had air cover to take risks, then use those reference accounts to expand into more conservative functions once the approach was validated.
Stacy Edgar
Co-Founder & CEO of Venteur
Benefit From Category Pioneers' Mistakes Without Being First Mover
Stacy deliberately positioned Venteur in the strategic middle ground of market timing: “no longer the new kid on the block, but we’re not the first mover at all, either.” This let her exploit a critical advantage—learning from competitors who had already paid the education and execution costs: “we’ve kind of benefited from others educating the market and kind of getting a few black eyes, unfortunately, to an implementation. And that’s where we’ve incorporated those lessons learned on product.” Being second or third in an emerging category meant Venteur avoided spending cycles and capital teaching buyers why ICHRAs mattered (pioneers had done that work) while building superior product by studying where early movers had failed in implementation. Stacy was “super excited” when newcomers entered because it provided “market validation that this model is picking up” without threatening Venteur’s improved execution. The lesson: first-mover advantage is overrated when you can let others absorb the arrows while you build a better mousetrap informed by their wounds.
Nan-Wei Gong
Founder CEO of FIGUR8
Identify Who Has "Most To Lose" To Find Economic Buyer In Multi-Party Markets
In healthcare’s three-party system of payer, provider, and patient, Nan-Wei used a straightforward heuristic to cut through complexity: “understanding there are different types of payers, I started like, okay, who has the most to lose? So we really just follow the information and follow the money and find these big larger insurance companies and call them on LinkedIn.” This approach prevented the common founder mistake of selling to end users who don’t control budgets—she warned that “it’s very easy for a technology founder like myself to think that the doctors are the buyers and they are just not.” Her “detective work on who makes decisions, who should be signing the contract” became “the top one priority” because even though the “doctor’s therapist might be the one using it, they’re not the one that’s going to be in the commercial transaction with you.” By identifying which party had the most financial exposure (insurance companies facing claims), FIGUR8 found the true economic buyer and built their GTM motion around that stakeholder rather than the obvious but wrong target.
Joshua Miller
Chief Executive Officer of Gradient Health
Work Within Existing Frameworks While Pushing Incrementally In Regulated Markets
Unlike aggressive disruption strategies that work in other sectors, Josh learned healthcare demands a fundamentally different GTM approach: “you kind of want to work within the existing frameworks that people are comfortable, but push a little bit on what’s acceptable, what should be done.” He recognized that medicine’s incremental pace exists “for good reason” because “you want things to kind of move at a pace that is, let’s say, has its checks and balances in medicine and doesn’t move too fast. Right. That’s how you end up with problems.” The fatal mistake was the arrogant outsider positioning: “you don’t push too hard and come in and say, oh, I know the better way to do this. Right? You’re never going to get buy in if you do.” This meant Gradient Health positioned as an evolution of existing clinical trial processes—making them 10x cheaper and faster—rather than claiming to reinvent medical research entirely. The lesson: in regulated markets, frame innovation as improvement within accepted paradigms, not revolutionary replacement of them.
Aasim Saeed
Founder, CEO of Amenities Health
Use Provocative Branding To Signal Category Differentiation
Aasim deliberately rejected traditional healthcare visual language to signal Amenities solves a fundamentally different problem than incumbents. “Healthcare is really bad at experience. We just established that, right? We don’t need establishment. Everybody knows that. If we’re coming in and we’re saying we’re really great at experience, why would we want to look as awful as healthcare does?” The branding choice wasn’t aesthetic—it was strategic positioning that reinforced their core value proposition. “We’re not trying to take over their brand. We’re not making Bailey, Scott and White put trees on their logo. We’re just saying that, like, we fill in a gap that you don’t have.” Rather than looking familiar to conservative buyers, Amenities used visual differentiation to demonstrate they possessed capabilities health systems lacked. “You need to stand out. Right? And honestly, but look, we are trying to be a lifestyle brand. But like, I would wear this, like, I wouldn’t wear, you know, like every other startup on my jacket type of thing.”
Cesar Herrera
Co-Founder & Chief Executive Officer of Yuvo Health
Understand True Buying Motivations Beyond Rational ROI
Cesar launched with messaging focused on capabilities and ROI, assuming rational business cases would drive partnerships with health centers. “When we first started, we really pushed that the most of, here are some capabilities that we know our health center partners are not allowed to build, do not have the capacity to build. And simply by selling that story, we thought that our health center partners would be compelled to partner with us.” He realized quickly this approach failed because health centers faced political and regulatory pressures that overshadowed capability gaps. “We realized really quickly that wasn’t the compelling story, but rather speaking to the political pressures and how we can work with them to support and uplift them.” His core advice became understanding “the motivations of your customer and their quote, unquote, buying decisions. Because if you don’t understand that, regardless of how great your solution is, you’re not going to be able to sell it.”
Amy Brown
CEO of Authenticx
Differentiate On Outcome And Scope, Not Just Technical Approach
Amy acknowledged direct competitors in speech analytics who listened for sentiment and helped contact centers intervene in escalating conversations, but positioned Authentics on a fundamentally different dimension. “There are companies out there that are speech analytics companies, right? That are listening for sentiment, that are trying to help businesses know how to intervene in a conversation when a customer is escalating or they’re frustrated to help that agent or that contact center do better.” Rather than competing on technical features, she differentiated on business outcome and analytical scope: “I think where we’re different is the outcome and what we’re trying to do with it. We like to take a very macro lens to solve big problems with this data. We are less focused in changing that individual, singular conversation between a contact center agent and that customer.” This positioning shift moved the competitive battlefield from feature comparison to strategic business impact, targeting executive buyers solving enterprise-level problems rather than operational managers optimizing agent performance.
Brock Leonti
CEO & Co-Founder of Prescribe FIT
Build Category Through Education-First Content When You're Competitorless
Brock positioned Prescribe FIT as the definitive voice in a new category by producing educational content that taught the market before selling to it. “We stand truly competitor less” in remote physiologic monitoring for orthopedics, which created both opportunity and obligation to define the space. His team “put out case studies, we put out white papers on different subjects, so that way it educates the market on what prescribed fit is. But even higher than that, what remote patient monitoring can do for the practice.” This layered approach established category-level authority before product-level differentiation. Brock’s VP of marketing built “a ton of content” that positioned them as thought leaders educating physicians on digital health capabilities, not just vendors pitching a solution. Without competitors to define the category, Prescribe FIT owned the narrative by teaching practices “how it helps improve the other treatment options that have been there in our traditional and orthopedic care.”
Danny Freed
Founder & CEO of Blueprint
Wait For Product-Market Fit Before Forcing Category Creation
Danny spent years pushing category creation uphill before realizing the sequence was backwards. “For many years we’re really trying to go and create this category and it almost felt like we’re climbing uphill without real product market fit.” The breakthrough came when he stopped forcing it: “Now that we have product market fit, it feels like that category is being created and it’s actually a good thing. We’re not the only ones pushing that category forward. We have competitors, which actually is a really good thing.” Competitors joining the space became an asset rather than a threat because “the education of the market is happening sort of with or without us, which we didn’t have as much in sort of the measurement based care space.” Category creation became effortless once the product had pull—the market educated itself through multiple players rather than requiring Blueprint to do all the evangelism work alone.
Itzik Cohen
Co-Founder & CEO of PayZen
Don't Hire CRO Until Founder Has Complete Sales Motion Mastery
Itzik’s biggest hiring regret was bringing in sales leadership before nailing the motion himself. “Don’t hire your chief sales or chief revenue officer too early. You think you’re ready for scale, so you want to get your sales team growing and you need somebody who comes and scaled the business. You’re probably not ready.” The problem wasn’t talent quality—it was timing and tacit knowledge transfer. “You’re going to be the number one sales guy for the company for quite a while. And any professional you’re going to bring who’s potentially an amazing sales guy or a sales operator will not have the gut feel and will not have the iterative kind of discipline you have about what works, what doesn’t work, when needs to be improved.” Itzik emphasized understanding “how is that flowing into your sales material? How are we articulating the value of the company in the right way” before delegating. Even years into PayZen’s journey, “only now we’re thinking about it, we still don’t have one.”
Austin McChord
Chief Executive Officer of Casana
Trust Founder Gut Over Expert Advice When You See Differentiation
Austin’s biggest regrets at Casana came from deferring to domain experts when his instincts signaled a different path. “I think the places that I’ve stumbled most are the places where I’ve been talked out of something or experts have said, don’t do it this way, and then went with the experts when my gut was like, oh, maybe we’re different, and here’s why we might be different.” The cost was substantial: “wow, we lost six months because of that.” His advice to his past self was simple: “trust your gut more…I should have fought a little bit harder on the contrarian opinions.” The challenge wasn’t rejecting expertise entirely—it was maintaining conviction when the company’s unique positioning justified a contrarian approach. “It’s hard when you have a contrarian opinion, and I guess you’ve always got to be good at justifying it because you can’t just tell people to do it because you’re the boss.”
Kyle Kiser
Chief Executive Officer of Arrive Health
Customize Marketing Messages For Each Stakeholder With Veto Power
Kyle faced a complex B2B environment where multiple stakeholders held veto power over purchasing decisions, requiring completely different value propositions for each role. “There’s this role called a chief medical informatics officer…that person is there to only represent the voice of the user…And then there’s the chief information officer, who’s actually the one that likely is saying yay or nay on what goes into that electronic health record system. And then there are a bunch of other sort of business stake owners.” Kyle built distinct narratives for each: “In the user case, there’s a really important quality and objectivity argument to be made for our tools. For the chief information officers, it’s all about the ease of implementation and use and the support that we can provide so we make their lives easier, not harder.” His conclusion was direct: “the marketing message is mixed, really. It’s that it has to be very specific and targeted really specifically, because otherwise it’s just too complex a sales environment to just have one big blast marketing message.”
Andreas Cleve
Co-founder & CEO of Corti
Engage In Policy Formation To Shape Future Regulatory Landscape
Andreas recognized that operating at the edge of critical AI technology created opportunities to influence the rules governing his market. “We’ve been lucky to be invited to be a part of digital Europe where we’ve been a part of coming up with suggestions for legisl” on AI healthcare regulation. This wasn’t altruism—it was strategic positioning. Beyond Brussels, Corti extended this approach: “we’ve been doing that in Scandinavia and here in Denmark as well.” Andreas framed policy engagement as an inevitable responsibility: “that’s sort of a weird part of being at the edge of important technologies, that you sort of have a societal responsibility and skill involved.” For deep tech founders in regulated industries, shaping future regulations isn’t optional—it’s a competitive necessity that determines whether your category design aligns with or conflicts with emerging compliance frameworks.
Rishi Nayyar
Co-Founder, CEO of PocketHealth
Meet Consumer App UX Bar, Not Incumbent Healthcare Software Standards
Rishi’s outsider advantage came from benchmarking against consumer tech rather than healthcare incumbents. “Our bias is, how are these problems solved in the entirety of tech, in the entirety of consumer applications? Not, hey, what are other patient portals that we can look at? Because typically that’s not the bar that you want to be meeting.” He set the standard by asking whether users could transition seamlessly between best-in-class consumer experiences and Pocket Health: “You want to be meeting the bar where the patient can go from Uber into pocket health. And they feel that these are applications that feel similar, that have been thoughtfully designed in the same way that when you click a button, it responds, and the button is probably where you expected it to be.” Rishi acknowledged the opportunity this created: “these are pretty basic things, but a lot of healthcare doesn’t work like that. Again, the bar is low.” Coming in without healthcare baggage meant “you could take that high bar that you find outside of healthcare from a tech perspective and bring it in.”
Samson Magid
Co-Founder & CEO of HealthSnap
Use Top-Down C-Suite Sponsorship To Overcome Boots-On-The-Ground Resistance
Samson faced a structural challenge in large health systems where executive enthusiasm didn’t translate to physician adoption on the ground. “There is a weird dichotomy, because you have the enterprise systems that have their C suite and executives driving the initiatives like ours and saying, hey, we’re going to be progressive, we’re innovating in this space, we’re going to do this. And then you get the kind of boots in the ground physicians that can be resistant to actually adopting this for their patient populations.” His solution was deliberate bifurcation of messaging and stakeholder management: “There is a really tight balance of us working with executives at the C suite who are clinical in nature and saying, hey, here’s how this is going to work. Here’s how we’re implementing it and here’s why it’s better for your patients and our system. And then with us being able to execute and say, hey, we’re going to walk you through every step of the way. We’re not adding more work to your plate as a doctor.” The C-suite mandate created air cover for ground-level adoption: “that’s the type of like top down approach that we’ve taken that we found to be very successful.”
Viral Patel
Founder and CEO of Radish Health
Build Convenience Into Behavior Change Strategy, Not Just Education
Viral learned that patient education initiatives consistently failed to shift utilization patterns because they ignored the convenience gap. “I think that people really value convenience. And if you want to change behavior, the behavior you want people to change into has to be a convenient thing.” He observed this pattern repeatedly across healthcare settings: “we talk to folks all the times that go, you know, we’re doing a lot of patient education around getting them to not use urgent care and go to their primary care doctor instead. But then if you ask the patients why they don’t do that, and they’re like, well, it’s not convenient. I call the doctor’s office and they’re not available till next week, but the urgent care is available in ten minutes.” His lesson from both Oscar and the ER was clear: “I think you need to provide a great service, and that great service needs to be convenient and accessible as well.” Education without convenience solves the wrong problem—users already know the optimal behavior; they need the optimal behavior to be easier than the suboptimal alternative.
Dipanwita Das
CEO & Co-founder of Sorcero
Quantify ROI In Time Saved, Cost Reduction, And New Capabilities
Dipanwita built Sorcero’s ROI story around three metrics that map directly to CFO concerns: faster, cheaper, better. “If they were spending three days doing something, they’re now spending two hours doing the same thing,” she explained, with customers averaging 92% faster on tasks. The cost reduction wasn’t just about software pricing—it was about collapsing the entire stack. “It’s cheaper for them to use a single piece of software rather than have a collection of tools and data subscriptions and also pay consultants and also hire people.” The third metric, better quality, unlocked the strategic conversation: “They are able to have insights into their data, their customers, and their products in a way that they were never able to do before. And they can measure it.” This framework gave customers concrete proof points while building the case for transformation.
Henry O'Connell
CEO, President / Founder of Canary Speech
Persistence And Patience Are Non-Negotiable In Healthcare GTM
Henry worked with one healthcare organization for five years from first board presentation to commercialization, staying connected because the relationship provided critical operational insights. “You’ve got to ask yourself, what is it I want to do? Because that’s the stake you put in the ground, and you hope that stake is just three years away,” he explained, before adding the reality: “that stake may be three years out, it may be eight years out, it may be 10 years out.” Healthcare markets resist change because “their processes, their procedures, the tools they use are being used in situations and circumstances that are critical, life saving in many cases.” When the pandemic hit, healthcare institutions became too busy for product development partnerships, forcing founders to maintain conviction through external disruption. Henry’s core advice was direct: “Be willing to recognize that and be persistent in believing you can get there.”
Kourosh Davarpanah
Cofounder & CEO of Inato
Avoid Overfitting To A Single Enterprise Customer, Even When Desperate For Traction
Kourosh’s advice for enterprise founders starting over was clear: “Partnering with enough clients so that you’re not overfitting to begin with.” Inato made the classic mistake of needing early validation: “We focused so much on a single one that we ended up building something that was super customized to them, which was a blessing and a curse because we ended up getting early traction, but we ended up doing 90% of our revenue with them.” The cost was substantial technical debt. “We actually then had to backtrack a ton to be able to understand what is completely specific to this pharma company. And how can we actually build a product that fits a need in the market and not just for a single customer?” The early revenue came at the expense of building something repeatable — a tradeoff that delayed their ability to scale beyond one anchor account.
Ty Allen
CEO of SocialClimb
Hire Product Managers With Domain Expertise Over Product Management Experience
Ty made an unconventional hire that shaped SocialClimb’s product-market fit: a healthcare marketer with zero product management background to lead product. “I made the decision that getting an expert in the product needs is more valuable than getting someone with expertise in product management,” he explained, betting that understanding healthcare marketing problems mattered more than knowing product frameworks. The marketer learned product management on the job while bringing deep customer insight. “This guy has learned how to do product management and couple that with his understanding of product or of marketing in healthcare. That’s helped us deliver the right features that seem to really hit the sweet spot with these groups.” The timing proved fortunate—their feature set matched exactly what private equity operations teams wanted when taking control of practices, something a traditional product manager without domain expertise likely would have missed.
James Bates
Founder, CEO and Chairman of AdviNOW Medical
Deep Operational Immersion Reveals Root Cause Economics That Customers Can't Articulate
James didn’t rely on customer interviews to understand the healthcare problem—he embedded himself in operations and ran a six sigma cost analysis. “I cost every single movement in the clinic from the time the patient goes in. What does a front desk do? Do they have to stand up three times? Do they go to the printer?” This granular economic modeling revealed the core insight: “2/3 of a Physician’s time was spent doing activities that there was no regulatory reason for them to do. They just happened to be the one with the knowledge. So they were doing it.” Physicians knew they hated the work—when asked “what is the worst part of your job?” they said “charting” and “documentation”—but couldn’t quantify why low single-digit EBITDA persisted despite massive healthcare spending. James’s operational immersion uncovered the economic root cause that shaped Advanow’s entire positioning: physicians had become “the most expensive clerk on the planet.”
Dr Thomas Oakley
CEO of Feedback plc
Enterprise Healthcare Sales Require 10-30 Touchpoints Before Contracting
Thomas quantified what most founders underestimate about healthcare sales cycles: “It takes anywhere between 10 to 30 engagements before you get to the point of contracting.” The process didn’t end there—after those touchpoints came procurement, which “can take six to nine months, depending on the complexity.” Only then did implementation begin. Healthcare decisions happened “by committee because they have to involve multiple stakeholders from multiple areas of the hospital,” making abbreviated sales cycles impossible. When asked what drove Feedback’s 74% year-over-year growth despite these obstacles, Thomas’s answer was direct: “Persistence. It takes a lot of internal discipline and drive to keep pacing and chasing and pushing and to not give up on opportunities and to ensure that you close them.” Healthcare GTM required organizational endurance, not sales efficiency hacks.
Matthew Stoudt
CEO of AppliedVR
The "Three E's" Framework Prioritizes Ease Of Use Over Technical Sophistication
Matthew built Applied VR’s product philosophy around a strict hierarchy: “ease of use, engagement is the second one…and then the last piece is the efficacy.” His reasoning was blunt: “I don’t care how efficacious it is, I don’t care how engaging it is. If it is complicated, it is hard to use…the patient’s never going to use it. It’s going to sit in a corner and gather dust.” This wasn’t theoretical—they originally used a pulse oximeter attached to fingers via Bluetooth to drive breath experiences, which was “awesome” in labs but failed when deployed. “You send that into a home to a 55 year old male, female, whatever, and they got to put a pulse, what, on their finger? I don’t have blue teeth. What are you talking about? Right, it’s going to fail.” They replaced it with simpler breath detection, accepting technical trade-offs to eliminate adoption friction. Matthew’s principle: “If you get the first two, you’re going to get the third on this”—nail ease of use and engagement, and efficacy follows.
David King Lassman
Founder of GigXR
Trade Shows Provide Highest-Fidelity Demos For Experiential Technology
David built GigXR’s sales motion around a dual approach after learning remote selling during COVID, but recognized the hierarchy of conversion effectiveness. “It’s more powerful if we can get in the room with customers because when you see this up close and personal, it’s the most compelling experience of all.” For mixed reality technology that buyers had “had no experience of,” creating “this moment where the jaw dropping moment where they say, oh my God, that is so cool, I have to have it” required physical proximity. Remote demos through mobile phones worked and enabled global selling, but “trade shows are very good for us” because the experiential nature of the technology demanded the highest-fidelity demonstration environment. GigXR made sure “we represent the biggest and the best of them” in healthcare, using trade shows as their primary conversion channel while supplementing with remote sales for reach.
Alex Zekoff
Co-Founder, CEO of Thoughtful AI
Message To Outcomes Executives Care About, Not Technical Capabilities
Alex’s early website messaging was technical ego with zero business resonance: “I think we even had, were testing the tagline, our bots are better, faster, smarter which doesn’t really mean anything to anyone.” The pivot came when he stopped talking about bot superiority and started speaking CFO language. “We help mid market healthcare providers get paid all of their money faster,” he explained, translating technical capability into cash flow impact. The specificity mattered—moving collections from 65-70 cents on the dollar to 95 cents, and reducing day sales outstanding from 50 days to five days. This outcome-focused positioning made ROI modeling straightforward because it mapped directly to metrics executives already tracked in their P&Ls.
Daniel West
Chief Executive Officer of Prospection
Category Design Must Be CEO-Led Or It Will Fail
Daniel learned from multiple category creation efforts across his career that executive sponsorship determines success or failure. “If it’s not being led by the CEO, it’s highly unlikely that it’s going to work. It’s either got to be led by the CEO, or the CEO has to make it a core pillar or has to believe that it is a core pillar in their success and the success of the business. Otherwise, it’s probably not worth engaging in the first place.” Category design isn’t a marketing exercise—it requires “changing the way that you execute your business strategy as an organization” including messaging, sales enablement, buyer identification, and processes. Without CEO commitment, these organization-wide changes won’t happen. Daniel emphasized persistence: “This is not something that you do and you run it for six months. This is something that becomes ingrained in the business for the foreseeable future.”
Vicky Demas
Chief Executive Officer of identifeye HEALTH
Phase Your Go-To-Market Launch Around Awareness In Targeted Segments First
Vicky resisted the temptation of a broad launch, instead focusing on “creating awareness is key, but it’s in a very targeted way” before scaling. Her approach was deliberately sequential: “we’re starting in a very phased and thoughtful way, trying to build the right partnerships” with early customers and KOLs who could validate both product and messaging. She leveraged KOLs as “sort of like the influencers in our space” to “help us build our brand and gain earned media” rather than making broad marketing claims. This let Identifi work “in partnership with our customers to solve the problem that is most important to them” before expanding, using early adopters to prove the concept worked in real workflows. The narrow focus allowed them to be “agile in implementing changes” based on partner feedback, building credibility through earned media rather than paid awareness.