Ten Q's for Qumis
Getting to know Dan Schuleman, the founder/CEO of Qumis.
Congratulations again to Dan Schuleman, Shiv Sinha, and the rest of the Qumis team on closing their $2.2 million seed round, which Armory Square Ventures had the privilege of leading. Not long after setting up shop in his new Chicago HQ, Dan sat down with ASV partner Neenah Jain and associate Preston DeGarmo to discuss his journey from insurance law to entrepreneurship, the inspiration behind Qumis, and how he’s leveraging his domain expertise to stand out in a crowded AI landscape.
ASV: Dan, tell us a bit about your background before founding Qumis.
DS: Sure. I started as an insurance coverage attorney, representing insurance companies in claims disputes. That role required deep expertise in policy forms and regulations, as insurance is state-regulated. Eventually, I moved in-house as the second legal hire at Kin Insurance, which is now a unicorn here in Chicago. At Kin, I transitioned into a general corporate counsel role, gaining insight into high-growth, VC-backed businesses and insurance operations. That experience, coupled with my frustrations with industry inefficiencies, inspired me to start Qumis.
ASV: Was there a specific lightbulb moment along the way?
DS: There were three, actually. The first was in my first week practicing law, when someone plopped a three-ring binder on my desk with a policy in it. They handed me some highlighters and Post-it notes and said “mark it up.” It seemed ridiculous, but that was how everyone did the job at the time. Second, I worked on a coverage lawsuit about damage to the roof of a hotel, where an insurer failed to send a crucial letter on time, leading to an unbelievably costly dispute and a huge mess to clean up — all over a silly mistake that could’ve easily been avoided. That inefficiency stuck with me.
Finally, when I was diving into financial reporting, I found that U.S. property and casualty insurers spend $20-30 billion annually just on adjusting claims — just adjustments, mind you, not even including the claims payouts. That revealed a huge opportunity to streamline operations: in claims alone there was a venture-scale business to be built.
ASV: Are there any existing tools halfway between the old-school, three-ring binder approach and what Qumis offers?
DS: Some folks use Adobe Acrobat to highlight PDFs, but the main competitors are spreadsheets, PDFs, and people’s brains. And phone calls. Apart from that, there really isn’t a modern solution automating policy analysis at scale.
ASV: Tell us about Shiv, your technical co-founder.
DS: Shiv is fantastic. We met through a mutual connection at Kin. He was looking for a vertical AI company, and after deep conversations — including a thorough co-founder and advisory vetting process, which he passed with flying colors — he came aboard. Our working style is highly efficient. I’m definitely a pace-setting leader, always hustling and rolling up my sleeves, and Shiv operates at a similar pace. He can build without needing traditional product development bureaucracy, which is extremely valuable at our early stage. I can describe an idea, an objective, and some solutions I’ve thought of, and he’s very adept at taking the baton and running with it, and just building. At Goldman, he scaled a team from five to 80, so I trust him to grow our technical team as we scale.
ASV: How did you come up with the name Qumis?
DS: It’s inspired by “Cumis Counsel,” a legal concept in insurance where policyholders have the right to their own, independent legal representation that’s paid for by the insurance company — the goal being to avoid a potential conflict of interest since the insurers are footing the bill. We changed the ‘C’ to a ‘Q’ for branding purposes, playing on ‘queries’ and ‘questions.’
After picking the name, I learned that there's a city called Qumis in Iran. And so for the first year of Qumis, our SEO did not beat out the Wikipedia page for Qumis the city, but I think now we finally have.
ASV: How do you approach branding and storytelling in an industry that’s often regarded as dry, ultra-technical, and inaccessible?
DS: We aim to simplify and demystify insurance, which is definitely a black box for many people who interact with the industry. It’s a really weird product because you’re literally buying a legal contract with a promise. Our goal is to make coverage analysis intuitive, saving time and reducing risk. The more we refine our messaging—like branding our three main workflows as ‘The Three C’s’ (Counseling, Checking, and Claims)—the better we connect with customers.
ASV: With AI moving at a blistering pace, how do you approach building a moat? Do you worry about copycats springing up? How much time do you spend eyeing the sideview mirrors versus building with your head down?
DS: It’s a balance. About 60% of our focus is on customer acquisition and growth, while 40% is on building a technical moat. Distribution wins in the early days, but our defensibility comes from being the most accurate AI for insurance. While AI infrastructure evolves, we believe specialization and deep domain expertise will differentiate us.
ASV: What was your experience fundraising in this climate, and what advice do you have for founders?
DS: It was tough. Early-stage investment has slowed, and enterprise SaaS — where big revenue milestones take time — makes it even harder. Investors expect both strong revenue and a deep technical moat, which can feel like a Catch-22. The process forces you to refine your vision, though. I initially started with a narrow focus, but investors pushed me to articulate a broader, venture-scale opportunity. Fundraising is also emotionally taxing — having people critique your business while you’re all-in on it is tough. But persistence is key.
ASV: Tell us more about that broader, longterm vision for Qumis.
DS: Ultimately, we want to redefine how insurance policies are read. The industry runs on PDFs and outdated processes, with an aging workforce still using methods from the typewriter era. There’s a massive opportunity to modernize how policies are interpreted, analyzed, and leveraged. By capturing institutional knowledge and embedding analytics into the reading experience, we can unlock efficiencies and transparency.
When I used to read the policies at the law firm, I would think to myself: I know this one sentence has ten documents in my system that references it, and I know this person—Bob, let’s call him—has three different ways to interpret it. But which one is correct? Each sentence contains a universe of information that aids comprehension, and the same applies to the next sentence, and the one after that. Layers of meaning emerge from every word in these policies, shaped by history and the vast body of work that has gone into them.
The challenge is how to aggregate, condense, and distill this knowledge into a seamless experience. Doing so will unlock countless opportunities — not only accelerating the business of insurance but also ensuring that policies deliver on their promises. By making insurance more transparent, we empower people to understand what they’re buying, what’s covered, what’s not, and what to expect.
Unlike some startups that focus narrowly, replacing brokers or optimizing claims, we’re tackling the core of insurance: the documentation and the coverage itself.
ASV: Any entrepreneurs or companies that have been particular inspirations?
DS: Kin’s CEO, Sean, has been a huge inspiration — his approach to culture and execution is something I want to emulate. I also admire Apple and Brian Chesky of Airbnb. Apple’s design philosophy — where even a toddler can intuitively use an iPad — is something I want for Qumis. Too much enterprise software is clunky and frustrating. We want our product to be the opposite: powerful but simple.