Most health startups bill for the visit and move on. Sam Holliday designed Oshi Health to do the opposite - to put its own revenue downstream of whether a patient actually feels better. That is the whole bet. In an industry that has spent decades rewarding volume, he wired the incentives to outcomes and then went looking for the country's biggest health plans to sign off on it.
They did. Oshi Health is now the first nationwide virtual center of excellence in its specialty, available in all 50 states to more than 40 million in-network members. In October 2024 the company raised a $60 million Series C led by Oak HC/FT, with existing backers Bessemer Venture Partners, Flare Capital Partners, Frist Cressey Ventures, CVS Health Ventures and Takeda Digital Ventures all coming back for more. Reporters called the round "impromptu." Holliday's own framing was simpler: the evidence was too strong to wait.
The long apprenticeship
He did not arrive overnight. Holliday has been working in digital health since 2013, back when the phrase still drew blank looks in boardrooms. He started his career as a manager at Accenture, then moved through senior roles at Greenway Health and Everyday Health, building data-driven patient acquisition and population health tools inside one of the country's top electronic medical record companies. He served as chief operating officer of Cecelia Health, a digital chronic disease management company, and then as CEO of Emelie Scientific, a clinical trials recruitment platform.
By the time he co-founded Oshi in 2019, he had already scaled companies across diabetes management, patient acquisition and population health. The pattern across all of it is the same: take a corner of medicine that runs on friction, and re-plumb it around the patient. He has called the work "completely redefining what high-quality, comprehensive care looks like" - not, he is careful to say, just tweaking the system.
The strategy hiding in the word "in-network"
The quiet radicalism of Oshi is not the video visit. Telehealth is everywhere now. It is the contract. Oshi built itself as an in-network virtual clinic, which means its services sit inside members' existing health plan coverage rather than bolting on as an extra a patient or employer pays for out of pocket. That single design choice changes who has to say yes. To grow, Holliday has to win over the slow, skeptical, deeply incentive-driven institutions that actually move money through American healthcare - the payers. He treated that not as an obstacle but as the moat.
The model now runs on a growing roster of in-person practice partners across the country, paired with a virtual multidisciplinary team, and it keeps widening: more provider groups, more payer coverage, new employer partners, and a planned expansion into Medicare populations beginning in 2025. By the time of the Series C, Oshi reported raising roughly $119.5 million in total to fund the build. The October round was the one observers kept describing as unplanned - a company that did not strictly need to raise taking the capital because the demand and the data were both in front of it.
The two degrees and one campus
Holliday is a Penn lifer in the academic sense. He earned a bachelor's in engineering from the University of Pennsylvania and an MBA in healthcare management from Wharton - two very different ways of looking at the same problem, both stamped by the same campus. The engineer wants the system to work. The MBA wants it to pay for itself. Oshi is what happens when those two instincts refuse to compromise.
He did not build it alone. Oshi was co-founded with Dr. Sameer Berry, who serves as chief medical officer and has been named to Modern Healthcare's list of the most influential clinical executives - a clinician-operator pairing that gives the company both a credible medical core and a builder's instinct for scale. As the business has grown, Holliday has staffed up around the next stage, bringing on new heads of technology and partnerships to carry the load that a 50-state footprint demands. The org chart tells you what the pitch deck only implies: this is meant to be infrastructure, not a feature.
What advice does to a founder
Ask him for the hardest lesson and he does not reach for a war story. He reaches for the inbox. "You'll get a lot of different advice, and it's really good to ask for different opinions," he has said. The trick is the next part. "Being judicious and knowing which advice to take and which advice not to - it's a good skill to have, and it's not easy to develop." Sometimes the well-meaning input simply does not survive contact with his model, his business, his industry. Learning to let it go, gracefully, turned out to be a core founder muscle.
The other muscle is endurance. "Healthcare is a very hard industry to innovate in," he has said. "There are a lot of forces and structures that are hard to move, hard to change." His fuel for the grind is not a spreadsheet. "I always open our Slack channel that integrates our patient feedback - it's always the patient feedback that powers us." It is the first thing he reads.
The man off the clock
He lives in New York City with his family. He is a stubborn Philadelphia sports fan who has somehow also adopted NYCFC, which is its own kind of optimism. And he keeps a side interest in neuroscience and physiology - the wiring under the hood of the body, which is not a bad hobby for someone trying to redesign how care reaches it. Recognition has followed the work rather than the personality: Rock Health named him to its Top 50 in Digital Health as a "System Disruptor," the kind of label given to people who move structures that were supposed to be immovable.
What separates Oshi from the long graveyard of well-funded health startups is that Holliday refused the easy version of the business. The easy version sells software to a hospital and counts logins. The hard version takes responsibility for outcomes, signs value-based contracts where payment is tied to results, and lives or dies on whether the numbers hold up under scrutiny. He chose the hard version on purpose, because it is the only one that aligns a company's survival with a patient's. It is also the version investors as varied as a payer's venture arm and a pharmaceutical company's digital fund will underwrite together - an unusual coalition to find on a single cap table.
The ambition from here is unsubtle. Expand into Medicare populations. Add more provider partners and payer coverage. Prove, at national scale, that value-based virtual care can hold up in the parts of the health system everyone else finds too hard. Holliday has spent a decade being early. He seems comfortable being early a while longer.