2026 Ones to Watch - Industry Leaders: Steve Carroll, Findigs

“Steve co-founded Findigs with his college roommate and grew it into a leasing decision platform trusted by over 500,000 rental units. His company gives property managers an automatic yes-or-no on every applicant, backed by the industry’s only contractual fraud guarantee. He moves fast, holds himself accountable, and believes in protecting renters and property managers alike.” 

What recent accomplishment or initiative are you most proud of, and what impact did it have on your firm, clients, or community?

When renting a home, the biggest question is always “Will I be approved?” For decades, that answer has depended on slow, manual reviews by leasing teams, often taking days. Years ago, we made a bold bet: build an autonomous engine to handle the entire underwriting process, and that clients would want to take that work off their teams. The results have been transformative. Approvals now happen 24/7 in minutes, increasing conversion and reducing evictions by up to 90% without sacrificing accuracy.

What is one major challenge you’ve overcome as a leader, and what did it teach you?

Early on at Findigs, I thought speed and quality were the same fight. They’re not. We were growing fast, signing new clients and moving at a startup pace. But I saw gaps between what we promised and what we could deliver on day one. Not failures, but close calls that erode trust if you don’t catch them. So I made a change. Not to slow down, but to keep speed from coming at the client’s expense. We rebuilt onboarding to move just as fast and be ready when a client goes live. We didn’t get slower. We got more honest about what ready looks like.

How do you inspire, motivate, or mentor others within your organization?

I hold weekly office hours, open to anyone, no agenda. Sometimes a sales rep walks through a deal that went sideways. Sometimes an engineer pushes back on a product decision I made. I want that. If people aren’t comfortable challenging the CEO, something is broken. We’re making decisions that determine whether someone gets approved for a home. I take that seriously and expect my team to do the same. I also push people beyond their own perspective. You can’t build a fair product if everyone sees the world the same way.

What advice would you share with emerging professionals striving to become future leaders in commercial real estate?

Something my first boss told me that stuck: never treat your transactions like relationships and never treat your relationships like transactions. On Wall Street I watched people get that backwards all the time. When I left finance to start a restaurant tech company, and later Findigs, it was the relationships I’d built, not the deals I’d closed, that mattered. My other advice: don’t fall in love with your first product. We started Findigs as a rent payment app, but rebuilt around underwriting. That pivot was scary and the best decision we made.

Who has had the greatest impact on your career or leadership journey?

Keith Gilvar, my co-founder. Best friends since freshman year at Colby. Built two companies together.