For Steven Caldwell, leadership starts with showing up.
It means being close to the work, close to the team, and close to the people learning how to build careers of their own. It means late nights, hard conversations, mentoring younger colleagues, and helping people push beyond what they thought they could do.
“We ask our team to do a lot,” he said. “They’re committing to clients’ goals. They’re committing to the work. You become so close to each other as a team through that intensity. You watch lives and careers take big steps and given our business community is pretty small, you tend to watch people develop beyond the days of working alongside one another. The experience that they have here is so important to how the develop and who they become in the future.”
That belief has shaped Steven’s career in commercial real estate finance. Today, he is Managing Director and Head of Large Loan CMBS within Real Estate Securitization and Capital Markets at Wells Fargo, where he is responsible for originating and structuring large-balance commercial mortgage loans for securitization. He oversees transaction execution across property types and capital structures, working with borrowers, investors, and internal partners to deliver customized financing solutions in the CMBS market.
Steven joined Wells Fargo in 2025 after 12 years at Barclays, where he served as Head of Originations. He brings more than 20 years of real estate finance experience to Wells Fargo, with deep expertise in large loan origination, underwriting, execution, and client relationships across both CMBS and balance sheet lending.
But his path into real estate finance was not straightforward. Early in his career, Steven had to fight his way into the field. After a difficult stretch trying to make a career shift, he remembers being told no again and again. When he finally got in front of the CEO of a public company, he could feel another no coming. So he made the case the only way he knew how: with hunger.
“I said, ‘I will work for free,’” Steven remembered. “I just need to make this happen.”
For Steven, that moment still carries a lesson he shares with younger colleagues: no one owes you anything. You have to demonstrate your commitment and show what you are willing to put into the world before you expect anything back.
That perspective connects Steven’s story to CitizensNYC. Across the five boroughs, the grassroots leaders CitizensNYC supports are also people who see a need and decide to act. They do not wait for someone else to fix the problem. They gather neighbors, build solutions, and push forward with the resources they have.
“Don’t assume that someone else is going to solve the problems for you,” Steven said. “Try to figure out solutions on your own; and if you can’tdo it on your own, figure out who can help you solve it….just don’t stop pushing forward.”
That is the spirit CitizensNYC exists to support. A small grant can help a neighbor become an organizer, a block association launch a project, a youth leader bring an idea to life, or a community group meet a need no one else has addressed.
Steven works on some of the largest commercial real estate transactions in the world. But he also understands that impact is not only measured by scale. Sometimes a small amount of support, placed in the hands of someone with vision and determination, can have an outsized effect.
Steven grew up on Long Island and started coming into the city for internships before eventually making New York his home. He now lives on the Upper East Side, in Carnegie Hill, where he and his family have been in the same building for 16 years. It is home. But he also loves the energy of SoHo — the architecture, the vibrancy, the young people out in the streets, the sense of the city constantly moving.
For Steven, New York is more than a place. It is possibility made visible.
“I love New York so much because, to me, it truly exemplifies the American dream,” he said. “Despite whatever circumstances you come from you have unparalleled opportunity in New York, which is complemented by the deterministic energy of people who are destined to succeed.”
He sees that in his own story, and in the “million stories” that make the city what it is: not one path, not one neighborhood, not one version of success, but a dense, vibrant mix of difference.
That is why being honored as a New Yorker for New York means so much to him.
“It is an incredible, incredible honor,” Steven said. “New York is full of millions of stories. It’s all of these things smushed into a tiny island that creates diversity in the experience and unmatched vibrance.”
When asked what makes him hopeful about New York, Steven chose one word: relentless.
New Yorkers, he said, are sturdy. They take risks. They come here to challenge themselves, build lives, find fulfillment, and push through uncertainty toward something better.
“New Yorkers push through barriers to create a a great and fulfilling life,” he said. “And I do think that ties back very well to what this organization does. It is people who are looking to improve their lives and the community around them in small-dollar ways that have big impact.”
We are proud to honor Steven Caldwell as one of this year’s New Yorkers for New York: a leader who understands that opportunity is builtthrough commitment, mentorship, trust, and the willingness to keep pushing forward.
His work reminds us of something CitizensNYC sees every day: New York’s strength comes from people who refuse to wait for someone else to solve the problem, and choose, instead, to build.
