A spotlight on Sully.ai
How serial founders built a culture designed for former founders
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All successful companies have at least one thing in common: they have effective people making decisions and getting things done. This sounds rather simple but if you ask any successful startup founder what is keeping them up at night—they will 99% of the time tell you something to do with people. Coordinating people. Hiring people. Empowering people.
People, and people-related stuff, can get (very!) complicated. And it gets all the more complicated when things are going well—when you are hiring like crazy and expanding very quickly. Software, by comparison, scales easily. Just buy more servers. Expand your architecture. Iterate. You will figure that stuff out eventually.
But people stuff? Culture? Not so easy to get right.
None of this should be shocking—you probably know all of this stuff already: “It’s hard to find great people.” “It’s hard to scale your culture.” “It’s hard to make lots of decisions quickly as a business.”
Right. Obvious. So what’s the solution?
We haven’t yet found a universal answer—but at least one tactic that seems to be working well for many startups we have talked to is to hire people who specifically have experience “being responsible for taking a project zero to one.” Basically, hiring people with some sort of entrepreneurial experience.
It could be at any scale—perhaps they previously worked on a side project or started their own startup or even ran a blog—because simply having had the experience of being responsible for starting something, and needing to deal with all of the associated challenges, is enough to teach you so many valuable lessons that are useful to scaling startups.
Having former founders around the company makes everything easier. They welcome chaos. They tend not to get spooked by hard times. They can thrive in ambiguous environments. They prioritize getting the important things done. And much more.
Most startups _want_ to hire people with entrepreneurial experience but rarely actually attract many. That’s because their approach isn’t conducive to actually attracting, converting, and retaining those types of people. But what would happen if you explicitly architected your company culture around that entrepreneurial identity?
Well that’s what Omar, Nasser, and Chaitanya, the founders of Sully AI did when they started their company in 2023. (Sully AI builds solutions to automate doctors’ administrative tasks with the aim of reducing misdiagnosis and enhancing efficiency. They are building what they describe as “the app store of AI agents for healthcare” - designed to help healthcare providers end to end deliver a better experience. They already have hundreds of healthcare organizations paying for their product. Here’s a video with customer reactions to some of their experience using Sully.).
Designing their culture began with the simple idea: “What if we created a team full of people with entrepreneurial experience? Who shared that entrepreneurial mentality…people who have started or made things (at any scale!). People who know what it’s like to really be responsible for something. People who have dealt with things breaking (because they inevitably do). People who actually understand the feeling of being a founder.” How great would that be?
Then they went out and built their entire company with that persona in mind. The culture. The processes. The vibes. Really everything they did was designed to attract, retain and empower entrepreneurial people in a way that’ll make them productive and effective at their jobs.
Fast forward just a few years and it seems to have worked. They have successfully hired numerous former founders and people with experience building their own companies and projects, and then united them together under a shared mission and purpose. (All the while building a product, getting hundreds of customers, and raising millions of dollars from top investors. Oh and, yes, they are hiring for basically every role!)
And so we thought it would be interesting for people to get an insider look at what this looks like in practice. What does it mean to architect your culture this way? How can other companies learn from this approach? How can you hire former founders? How does a team full of former founders actually perform?
All that and more below. Thanks again to the Sully AI team for sharing behind-the-scenes details with us.
So what’s the formula for building a culture that attracts and empowers former founders?
Well there’s not a single answer. Or at least not one we could find. But there are a bunch of things you can do that, when combined, seem to set your culture up for success (and have worked for Sully).
The first is to choose an ambitious problem. It’s tempting to start small and narrow in scope—perhaps it seems less scary. But small problems rarely attract people who think big. Start with an opportunity that’s sufficiently large so that an ambitious person could see themselves working in and around it for many years.
In Sully’s case, the opportunity is rather obviously ginormous. We do not need to write out a bunch of zeros to convince you that the healthcare industry is large or that healthcare organizations spend hundreds of billions of dollars a year paying administrative salaries. Though I guess we just kind of did. You get the point.
The next is to choose a problem-space that can motivate people by the potential for impact.
Sometimes people work on/in companies where even in the successful scenario, it’s not obvious the world will be so much better. Remind you that success is not easy or guaranteed—and so if you are going to take on a big challenge, you may as well make sure that the optimistic case is worth grinding for.
Again, this is not really a problem with healthcare. Everyone you meet has a personal story connected to times where the healthcare system failed them in one way or another. The Sully story is perhaps particularly personal for the founders: “Omar (CEO) grew up watching his mother, confined to a wheelchair and unable to walk. He later understood that her condition was due to a medical error. Chaitanya (CTO) endured two years of chronic illness. Nasser (COO) experienced significant inconveniences when navigating healthcare for his pregnant wife in the Bay Area.”
Finding an industry plagued by problems, ideally lots of problems, is very much a good thing to aim for. The thornier the better. And then what you want to do is give your team exposure to the problems (and/or hire people already familiar with the numerous problems in the industry).
In Sully’s case, they have a number of people on the team intimately familiar with all of the problems (and opportunities!) in the healthcare world.
“I’ve spent years in healthcare consulting and saw firsthand how broken clinical workflows are — the documentation burden, the staffing shortages, the burnout. I also founded a mental health company and have family who are clinicians, so I’ve seen both the system-level and human cost of inefficiency.”
“With a medical background and over a decade of experience building my own healthcare AI startups—followed by years in venture capital evaluating countless companies in the space—I developed a deep understanding of the challenges involved in selling into the healthcare industry.”
“My wife is a Nurse Practitioner at Children's Hospital in Denver, CO and I've seen too many nights where she has to spend 3-4 hours/night doing post visit notes. “
And then perhaps the most important step—the thing that so many founders get wrong—is you want to manage these people effectively by giving them the appropriate amount of space and guidance.
The right amount of guidance typically involves giving your team a compelling long-term vision. In the case of Sully, this means: "One Human, One Doctor" - they believe “access to a doctor is a basic human right and they want to build the best fully autonomous AI doctor to fix both the cost and access issues in healthcare. What motivates them every day is getting to the point where someone comes to us and says Sully saved their life, a friend's life for a family member's life because it prevented a misdiagnosis, caught something the doctor missed etc.” That’s their long-term vision.
They pair that with a near-term product plan, which is to build an AI Agent App Store specifically for Healthcare—a bunch of agents working in unison to help providers deliver an end to end experience (supporting with decisions, scribing information, interpreting results, being a receptionist, etc.).
There’s a lot more nuance but you get the idea. The combination—long-term vision paired with nearer-term product plan—is a useful mix to give entrepreneurial people.
Entrepreneurial people, while not always the best at picking company ideas, tend to be pretty effective at finding solutions to problems (even ambiguous problems!). They just need to know the general direction to run in - so if you can give them that exposure (i.e. help them see all of the opportunities and give them a high-level path forward to keep in mind), then they can start to solution-ing, so long as you stay out of their way and remove any blockers for them.
“Leadership is great at removing blockers. If there’s red tape, they’ll cut it. If you need resources, they’ll get them.”
“I think we have implemented just the right amount of structure to keep everyone focused without creating unnecessary bureaucracy.”
And then you basically repeat. You keep making sure your team is close to customers so they get continuous exposure to the real problems going on. And you keep iterating on solutions as you scale.
“Most days, I’m deep in customer conversations — discovery, demos, follow-ups — helping health systems and providers understand how Sully can actually solve real operational pain. That’s the core of it.”
“Even leadership is always out in the field—demoing, selling, troubleshooting. There is no hiding in ivory towers thinking anyone knows best.”
“The mornings typically kick off with a few standing engineering calls, followed by customer meetings focused on product feedback and implementation needs.”
The good news is that service-based industries—healthcare, law, finance, etc.—are so very much full of inefficiencies. There is really just so much opportunity for technology, especially nowadays with some of the advances in AI, to actually make a real difference.
“If you want to build and ship real AI that saves doctors hours every day — not just decks and demos, but actual deployed products — this is the place.”
“When I came across Sully, it was clear the team wasn’t just chasing buzzwords. They were building real tools that actually save time for providers — not just make admin work prettier. The AI agents are fast, flexible, and can slot directly into how clinicians already work, whether it’s scribing, coding, reception, or even workflow automation.”
That difference and impact is often beyond economics. These technologies are enabling you to impact the day-to-day life of your customers in a way that’s never before been possible.
“One provider told me Sully gave her “the first dinner with my kids in three years where I wasn’t thinking about charting.” That hit hard. Another time, we closed a deal where the CIO told us we out-executed three billion-dollar vendors in a two-week head-to-head — just by showing up, moving fast, and actually listening.”
“Ones that stick with me most are when a customer tells us Sully literally changed their life - not in some fluffy way, but in a real, measurable one.”
The same was probably not true a decade ago. It would have probably been really hard/even a bad idea to try to forcibly apply machine learning to these sorts of legacy industries. It would have not really worked in a reliable enough manner, and probably caused even more inefficiency. As a company, you may have gotten stuck in a sort of research mode with no real customer feedback loops.
AI has really unlocked an entirely new wave of opportunity.
“Sometimes it's just a matter of being at the right place at the right time. An investor told us a few weeks ago - if we had started this company in 2019, we wouldn't be in the great position we are in today as our architecture would be outdated. (We are really built for the AI era!)”
This presents a particularly exciting opportunity to entrepreneurial people—people who can stare at an ambiguous, uncertain problem and come up with ideas and experiments to find solutions.
That’s one thing the Sully team particularly looks for: “people who have shown the ability to take something from zero to one in the face of uncertainty. People who have resilience in coming up with hypotheses, seeing them succeed and also fail, and then trying again.”
Vetting for this mentality in an interview process is not particularly straightforward.
The Sully team approaches interviewing by doing a few different things - but probably the unifying thing they try to do is to get the candidate out of “interview mode,” where people tend to tense up and not really be themselves, and instead just be genuine. The Sully team wants to know what you are really like, so they can really figure out a win-win situation.
“I spoke with leadership early on, and it was clear they cared less about flashy resumes and more about whether you can execute, think critically, and communicate clearly. We skipped the typical drawn-out process you see at bloated orgs — no endless loops, no hypotheticals. Instead, it was real conversations about product-market fit, sales motion, and where they actually needed help.”
“One of the most memorable parts of the process was the hackathon-style challenge. I was asked to build a full application from scratch in under a day, while also sharing my thinking around product strategy and business impact. It was an intense but rewarding experience. I found this approach to be a thoughtful and effective way to evaluate engineers—it gives candidates the space to showcase not just their technical skills, but also their creativity, product sense, and problem-solving abilities in a fast-paced, real-world, startup context.”
“Our COO has a very unique interview style where he just asks you questions for 15 minutes non stop. Overall from the day I got in touch with the company to the day I got an offer it was a little over 2 weeks. So things move quickly here!”
Seeing what you are really like helps them figure out if you are more of a “missionary or mercenary.” The latter—perhaps the people just looking forward to a 9 to 5 right now, are not really a fit for Sully. As they are entering a period of rapid growth, they are looking for people who can get behind the long-term mission and really help do whatever it takes.
Sully is hiring for 26 roles right now across basically every department: customer support, engineering, partnerships, sales, and even an open-ended “former founder” opportunity. They are hiring remotely and in SF. You can learn more and apply here.
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