Stephen Ambrose has built his career in the crucible of startup sales—where deals are complex, cycles are long, and every move matters. From Oracle to founding his own consulting business, and now as a leader in Quilter’s go-to-market strategy, Ambrose brings both resilience and rigor to the table. His story shows how a startup’s first enterprise contract doesn’t happen by accident; it’s forged through persistence, adaptability, and the ability to build credibility fast. “You want to go into a household name big electronics company and sell a full price contract for six figures right out of the gate as your first customer. Like, yeah, you’re crazy, man.”

Humans in the Loop highlights these people behind Quilter—where ambition meets collaboration, and craft scales into lasting impact.

Origins

Ambrose’s path started with a blend of technical curiosity and sales ambition. Growing up in Conneticut, he joined a four-year engineering program in high school called Project Lead the Way. “I have a little bit of technical knowledge—enough to be dangerous. I know how to use AutoCAD and some more common CAD solutions.” But it was sales where his career took flight.

After graduating from UC Berkeley with a marketing degree, he cut his teeth at Oracle as an enterprise account executive. Then came a fast climb through agencies and consulting firms, where he learned the craft of diagnosing sales problems and delivering 70-page audits to companies struggling with growth. That combination of technical appreciation and go-to-market focus shaped his career as the person companies trusted to rebuild and scale sales programs from scratch.

Journeys in Engineering

Stephen’s journey has been defined by building sales machines in places where none existed. At Full Funnel, he became the only non-partner flying around the country to sell multi-year consulting retainers. Later, with Data Advantage Group, he grew revenue from $1 million to $10 million in ARR and landed deals worth half a million dollars each. “These were long sales cycles, small company… but the dollar amount on the sales cycles was usually around half a million dollars.”

That success led him to an ongoing role with a metadata management and data governance company where he manages major accounts. But it’s at Quilter where Ambrose has applied all those lessons most directly—rebuilding HubSpot from scratch, creating sales processes, and closing the company’s first enterprise customers. “The deal we closed was the initial point that Sergiy wanted me to come in at for pricing. Being able to close at the exact dollar amount with your first enterprise customer is just uncanny. It just doesn’t happen.”

Ambrose thrives in the chaos of startup sales, where scrappiness isn’t just encouraged, it’s required. “It comes down to being scrappy, but also being smart. Hustle culture is important at startups, but you want to make sure you’re hustling on the right thing—not just being busy to look busy.”

Why Quilter?

Stephen came to Quilter not through formal recruitment, but through cold outreach. “I saw Sergiy on LinkedIn living not too far from me, and I did some cold outreach to him. We ended up meeting in person… he ended up bringing me on board to lead the sales efforts.”

What excites him about Quilter is the freedom to build. With no legacy sales team, he had the green light to design strategy, pricing, and processes from scratch. “When you’re building it from the ground up, you’re getting someone that’s giving you the authority to do what you want and put that trust in you. It makes it a little bit easier.”

That culture of autonomy and trust mirrors what ambitious engineers value: the ability to execute quickly without waiting for layers of bureaucracy. “In the world of startup sales, it’s like, hey, I want to try this new sales strategy… cool, do it. You’re just able to accomplish what you need, and that’s great.”

Beyond the Workbench

Outside of work, Ambrose is a fierce competitor in the pool. A lifelong water polo player, he now coaches, manages, and competes with a men’s 30+ team that recently won back-to-back national championships. “We just got no budget and we were super scrappy, and anyway, we smashed [Olympic Club] in the championship this year by three goals and it was awesome.”

For Ambrose, water polo is more than a hobby—it’s a lifelong passion that mirrors the same grit and teamwork he brings to startups. “Yeah, man, this is what I’m most proud of. These are national championship trophies… I’m just very proud of that. It’s a beautiful sport that I hope to keep playing forever.”

And when it comes to food, he’s equal parts Italian flair and classic sales swagger: “Carbone is my favorite—Caesar salad tableside, spicy rigatoni, veal parm. Like any good salesperson, I know how to wine and dine.”

A Line to Remember

“In startup culture, we don’t have all the folks hired in different departments. Everyone’s got to wear multiple hats. Some people don’t like that. But for me—it’s about being scrappy, being smart, and making it happen.”