Reserv is an insurtech company and technology-enabled third-party administrator based in the United States and United Kingdom that specializes in modernizing property and casualty insurance claims processing through AI and automation, making data science, reporting, and APIs easily accessible and consumable for claim leaders, underwriters and partners alike.
To start, please talk about how you both had the opportunity to confound a startup as a four-person founding team. What sparked the idea for founding Reserv, and how does someone find their way onto the founding team of a company at such an early stage?
Matthew: Getting to be a founding team member is a lot like surfing: half of it is putting in the effort to paddle out to the surf break and the other half is serendipity, being at the right place at the right time on that surf break.
David: I’m a runner, not a surfer, but I share Matthew’s sentiments! For me, becoming a founding team member at Reserv comes down to sustained effort, earning trust over time, and consistently driving real impact regardless of the role. Our paths to Reserv weren’t defined by any single moment, but rather by a series of intentional experiences where we built credibility through high-quality work.
For me, I started at BCG as an associate, gaining broad exposure across industries while developing a foundation in structured problem-solving. Wanting to apply that toolkit in an early-stage environment, I completed an externship at Snapsheet, working closely with CJ Przybyl, another cofounder and current CEO of Reserv, and the executive team on go-to-market and corporate strategy. I built trust by consistently driving impact on the problems that mattered most to the business.
Matthew: And when you were done with your externship, you recruited me to leave BCG to be your successor at Snapsheet! David and CJ had created from scratch the MVP of a SaaS business at Snapsheet, which was a totally new product and business model, an internal startup. David passed me the baton, and I built the foundations David had laid. Our work enabled that SaaS business to go from zero to $10 million ARR (Annual Recurring Revenue) in three years.
David: After that, CJ remained a mentor to both of us over the years—and that trust carried forward. A few years later, while I was in business school, Matthew and I began working with CJ again. It was half a year before Reserv’s formal inception, and what started as exploratory work on a hard problem in our free time quickly evolved as conviction grew and capital aligned—so when the opportunity crystallized, we were the natural choices to join the team.
Matthew: That was the “effort” half. The “serendipity” half was that lots of venture capitalists had been mulling this precise subject and wanted to incubate a startup under our leadership. Generally, the real secret is that the “effort” is entirely about being kind and generous with your time and consistently delivering great work.
David: Joining a founding team is rarely about positioning yourself for a specific opportunity. It’s about doing excellent work, being reliable, and letting that compound into trust. Timing and circumstance matter, but when opportunities emerge, they favor people who have consistently shown up, delivered, and earned the confidence of those around them.
Joining a founding team is rarely about positioning yourself for a specific opportunity. It’s about doing excellent work, being reliable, and letting that compound into trust. Timing and circumstance matter, but when opportunities emerge, they favor people who have consistently shown up, delivered, and earned the confidence of those around them.”
Tell us more about the “founder mindset” and approach you have as founding leaders. What lessons have you pulled from other parts of your career?
Matthew: Startups and BCG case teams have some surprising things in common: One, we are both resource starved; there is not enough time, people, or budget to do all the things you ideally want to do. Two, we are both solving hard problems in the fog of ambiguity; you rarely know if you’re chasing down the right things at day zero. Three, the consequences of inaction are dire!
The founder and BCG mindset is this: be 80/20, or even 60/40, in everything needed to build conviction about what the maximally impactful things are; decisively start building or executing all those things in parallel; and rely on pivoting or iterating to adjust and steer as you unearth new data.
There’s a final one that is indispensable: grit. Things don’t always go well, and sometimes a metaphorical live grenade gets dropped in the middle of your company -and you just have to dive on it. Every BCGer has been there; you grit and do whatever herculean effort it takes to make things right. None of the founder mindset works without generous helpings of grittiness.
David: For me, the founder mindset is rooted in ownership and bias toward action, both reinforced long before Reserv. At BCG, you’re trained to take responsibility for outcomes, step into ambiguity, and move things forward even when the path isn’t clear. It’s the exact same mentality needed in a startup.
The key lesson I’ve carried forward is ruthless prioritization. Just like on any client engagement, there are always more good ideas than resources. Success depends on focusing on the few things that truly move the business and making imperfect decisions, executing quickly, and adjusting as new information emerges.
Finally, resilience and adaptability are essential. As a founding leader, roles are fluid and progress is rarely linear. Staying calm under pressure and doing whatever the business needs at the moment is critical. The founder mindset isn’t about having all the answers; it’s about ownership, adaptability, and forward motion.
Too many efforts in this space have chased point solutions or incremental automation—digitizing the status quo instead of reimagining it. At Reserv, we started by asking what outcome we wanted to deliver, then built both the technology and the operating model backward from there.”
Switching gears to your work, what have Reserv’s successes taught you about insurtech? What is the future of tech and insurance?
David: What we’ve learned at Reserv has reinforced that insurtech isn’t about layering technology on top of legacy models, but rather about questioning the fundamentals and rethinking work at each stage of the value chain. Too many efforts in this space have chased point solutions or incremental automation—digitizing the status quo instead of reimagining it. At Reserv, we started by asking what outcome we wanted to deliver, then built both the technology and the operating model backward from there.
Matthew: This is spot on: in our space, the future belongs to disruptors with operations vertically integrated with cutting edge technology. The Reserv team had this strong insight early on and built the company around it.
David: The biggest learning has been watching what happens when you embed real-time data and automation directly into the flow of work, not as a reporting layer, but as the decision engine itself. When technology actively shapes how claims get triaged, managed, and resolved in the moment, you unlock step function improvements in speed, quality, and cost.
Matthew: We’ve done this for everything from rebuilding QA around agentic AI to detecting and acting on AI-driven insights, live scanning all claims data all the way to super-exciting AI applications to empower our claims adjusters. That’s why we have mind-blowing results to show for it: resolution timelines nearly twice as fast in books we’ve taken over or dramatically cutting indemnity spend driven by people failing to identify and surge care to claimants who are vulnerable or in need. We’re in the helping people business. The faster we can get care to people in a bad situation, the happier they are and, consequently, the happier our clients.
David: Looking ahead, the future of insurance belongs to platforms that tightly integrate technology, operations, and human judgment. The winners won’t be those with the most sophisticated tools in isolation, but those that redesign workflows from first principles and use technology to enable people to focus on the moments that matter most.
A major focus of yours is building high-performing organizations, whether going from zero to one or from one to ten. In four years, you’ve helped build Reserv from a four-person founding team to over 600 people and are honing in on that milestone of milestones: $100 million ARR. What have you learned throughout the process?
David: Scaling a high-performing organization isn’t about layering on process, but rather it’s about being ruthlessly deliberate about what you refuse to lose. Early on, speed, ownership, and clarity come naturally because everyone’s in the same room. As you grow, preserving those qualities requires real discipline and intentional design.
One of the clearest lessons has been that leadership capacity is almost always the constraint. The ability to move quickly at scale depends on having leaders who can own outcomes, set priorities, and make decisions without everything routing through the founding team. Moving quickly at scale depends on having leaders who can own outcomes, set priorities, and make decisions without everything funneling through the founding team. We’ve invested heavily in people with that ownership DNA, and it’s what allows the organization to maintain momentum as headcount and complexity multiply.
Matthew: I couldn’t agree more. I periodically revisit a book called Warfighting, which is the core doctrinal book for the US Marine Corps, that reinforces what David is saying. The doctrine assumes the Marines are vastly outnumbered, operating far from home, and outgunned. Relevant to startups!
A core concept is “tempo.” If you can’t count on winning on numbers or resourcing, then you must win temporally—learn faster, think faster, decide faster, and move faster than everyone else does. Aggressively rest and recuperate and be ready to act at a moment’s notice. The reason why the founder mindset we talked about earlier is so important is that it enables a high tempo. It enables it when you’re founding leaders like us; and it enables it at scale if you develop that bias to action and have a high-iteration mindset across all your leaders.
David: We’ve also learned that structure should follow the business, not lead it. The right systems reduce noise and clarify decision rights so teams can focus on impact. But systems are only as good as the culture that animates them. At 650 people, ownership and execution matter as much as they did at only 4. That doesn’t happen by accident. It happens because you hire for it, model it, and refuse to compromise on it.
Getting from zero to one is about balancing speed with quality, while continuously reinforcing that culture is a choice, not a byproduct of growth.
Matthew: A great example of how we’ve applied these concepts is a crazy launch we did back in fall 2023. We had the chance to grow more than 20x our ARR by winning a global logistics carrier in a head-to-head race with a competitor. Our customer gave us 60 days to launch. We led our then-17-person team to not only recruit, hire, train, and onboard 40 adjusters and 20 call center reps, but also design and build the software. We hit the impossible deadline and outperformed; our competitor took twice as long, with hiccups, and we ultimately won more share of spend in the coming years.
That’s winning through tempo, applied; that’s moving quickly at scale, applied. Of course, the unfortunate thing is that the market now knows we operate at high tempo and we’ve led this exact ramp-up five more times since! “The only reward for good work is more work,” as they say.
What separates winning startups from the pack isn’t ideation (everyone has ideas); it’s execution. The best executing teams are ones that are high trust and high cohesion—they don’t magically appear. They become that way from repeated acts of reciprocated kindness and generosity, freely given with no expectations in return during tough times when it isn’t necessarily easy to be kind and generous.”
You’ve credited BCG with a lot of inspiration in this conversation; what advice do each of you, as alumni, have for current BCGers?
Matthew: I’ll bookend this conversation the way we started it to tie everything together: kindness and generosity. You asked about high performing teams, earlier. What separates winning startups from the pack isn’t ideation (everyone has ideas); it’s execution.
The best executing teams are ones that are high trust and high cohesion—they don’t magically appear. They become that way from repeated acts of reciprocated kindness and generosity, freely given with no expectations in return during tough times when it isn’t necessarily easy to be kind and generous. I was so fortunate to know kind leaders, specifically Sara Codella and WuDi Wu, who looked out for me; their mentorship drove huge unlocks in my development. My advice to BCGers is to practice that kindness and generosity every day while you’re at BCG.
David: My response also centers around what I miss most about BCG: the people. Sara Codella and the broader insurance practice had a profound impact on me, both during my time at BCG and now beyond. I stumbled into insurance initially, but it became a pillar of my BCG experience because of the quality of leadership there. My advice: actively seek out leaders you respect and want to learn from at all corners of BCG. Some of my strongest relationships came from people I never formally worked with, colleagues I shared an office with or grabbed lunch with who became trusted mentors and sources of perspective over time.
Beyond the people, BCG is an exceptional environment for growth if you’re intentional about it. The firm invests heavily in development, not just through formal casework and training, but also through less-traditional paths like externships and internal rotations. Pursue those opportunities aggressively. They push you into unfamiliar environments, broaden your perspective, and help you become a more well-rounded leader. The skills you build matter, but the relationships you form and the judgment you develop matter more. Those are the elements that compound over a career.
