Sherwood Callaway

Real talk, let me break down Sherwood Callaway, this dude is the real deal in the startup game. He’s a YC summer ’21 guy, so he’s been around that fast, high-stakes world for a minute. Before jumping into his own thing, he crushed it at Brex, one of those unicorns everyone’s talking about. He was the second infra engineer there, so he’s the type who’s been in the trenches during hypergrowth, building stuff that scales like crazy. That kinda experience? No cap, it’s gold.

Then, he jumped into founding his own company, Opkit, in 2021. This guy saw a huge problem in healthcare, insurance verification for telehealth and virtual clinics. Basically, he built a SaaS platform that makes insurance checks way easier and faster. And get this, Opkit wasn’t just some side project. They raised over a million bucks from big names like YC, Global Founders Capital, Mischief (yeah, the VC firm from Plaid’s CEO Zach Perret), and others. That’s major. They even launched some wild stuff, like one of the first AI-powered phone calling services for healthcare, holy shit, that’s next level.

And here’s the kicker, Opkit got acquired by 11x in 2024. That’s a huge win. After the buyout, Sherwood didn’t just kick back. He became the first engineering manager at 11x and led the charge on Alice, their AI SDR product. This guy’s all about making sure the tech actually works at scale, pushing boundaries with AI and automation. Building startups is just the start, he’s about creating real impact with the tech that moves the needle.

What does all this say about Sherwood? Dude’s driven by solving real-world problems, especially in healthcare and finance. He’s not just chasing fame or VC money, he’s about making a dent, building stuff that actually helps people. He’s got that rare combo: the deep technical chops from his time at Brex, plus the startup hustle to turn ideas into real companies that get acquired.

He’s based in Brooklyn, but his impact? Yeah, it’s nationwide. He’s proof that if you jump into the deep end, learn fast, and stay relentless, you can crush it. Sherwood Callaway is one of those founders who’s just getting started, and honestly? No Cap, he’s gonna keep pushing boundaries and changing industries.