I sat down with Ayo Omojola, VP of Product at Carbon Health, to unpack the craft behind building in regulated industries and the discipline of choosing the right problems. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas.
As we explored his time across healthcare and financial services, I was struck by how methodically he untangles regulation to reveal “the opportunities where it’s easy to stop.” That mindset—paired with his insistence on going “unreasonably deep” when building early products—mirrors the rigor I expect from high-performing product teams. It’s a reminder that in complex domains, product discovery starts with understanding constraints so thoroughly that they become catalysts for innovation.
Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. I couldn’t agree more. In my experience, a clear and deliberate bet at the outset compounds through product discovery, roadmapping, and execution—reducing thrash and sharpening the signal on product-market fit. The best product outcomes often stem from the discipline to say no until the “why now” and “why us” are undeniable.
If you’re thinking about starting a company someday, or you’re a product leader who hopes to help a new product take shape, this conversation will resonate. We talk about balancing speed with diligence, aligning teams around crisp context, and turning ambiguity into tractable work without losing sight of the customer. These are the muscles that separate good product management from product management leadership.
Even if company-building isn’t your immediate goal, there’s a lot to learn from the frameworks Ayo absorbed from exceptional operators. We dig into how to get better at process, how to set context so decisions scale, and why “optimizing for the outstanding” creates leverage across hiring, execution, and outcomes. I share where I’ve seen these approaches pay off in practice—especially during zero-to-one product discovery and early product roadmapping and sprint planning.
We also cover his management and hiring philosophy, including why he loves to hire former founders. I’ve seen the same pattern: ex-founders bring end-to-end ownership, a bias for outcomes over output, and a resilience that’s invaluable when the path is unclear. In fast-moving environments, those traits accelerate learning loops and raise the bar for the entire team.
You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App).
Inspired by this post on First Round.
Leave a Reply