Steve Carroll and the trouble with getting a yes

Steve Carroll knew something about the money inside a building before he knew how to get comfortably into one. At Nomura, he worked in securitized products, a world that makes cash flows legible to investors. As a young renter in New York, he encountered a more mysterious system: the one between finding an apartment and receiving permission to live there.

The contrast is a useful place to begin his story. Housing can be described in portfolios, income streams, and financial instruments. Then someone wants a set of keys, and the conversation becomes a collection of forms. An industry capable of organizing complicated investments can still leave a prospective tenant waiting for an answer. Carroll had a professional view of one side and a personal stake in the other.

He now runs Findigs, the company he co-founded with Keith Gilvar in 2018. Its work concerns rental underwriting and leasing decisions. The business has moved a considerable distance from its first rent-payment app, while staying close to the frustration that prompted it. Carroll’s career is interesting in the space between those two facts: a problem he kept, and a solution he was willing to replace.

A roommate before a co-founder

Carroll and Gilvar met at Colby College’s orientation, over lunch in Dana Dining Hall, with their families present. Carroll’s explanation was pleasingly ordinary: their mothers were worried about whether they would make friends. The mothers’ intervention produced a relationship that would eventually acquire a company attached to it.

They became roommates, studied government, and took part in debate. Carroll also played squash and golf. By senior year, the two were thinking about their move to New York and how to find somewhere to live. One early idea was a marketplace that would let people pass along rentals without the usual broker-mediated search.

There is something recognizable about that sequence. Graduation brings the promise of a new career, followed almost immediately by the question of where the graduate is supposed to sleep. An apartment search has a way of making a future feel wonderfully specific. It also supplies an education in other people’s rules.

Carroll went into finance; Gilvar became a consultant. The housing idea waited. In 2018, they started Findigs. Years later, Carroll credited Gilvar’s capacity to learn and apply unfamiliar technical concepts, saying, “I don’t know what I’d do without him.” A founder biography usually makes room for the moment of inspiration. Here, the enduring relationship deserves at least as much room.

The rent check was only the beginning

Before Findigs, Carroll helped build Seated, the restaurant app, and served as its chief operating officer. His work had already taken him from financial markets into the mechanics of a consumer transaction. A reservation and a rental application are different commitments, but both start with a person trying to arrange something in the real world.

Findigs initially tackled paying rent. Carroll has described a bank bill-pay failure in which checks stopped going out without his knowledge, nearly getting him evicted. The incident gave a familiar administrative task a sharp edge. Money moving through a system is reassuring only when it actually reaches the person expecting it.

The team went looking for other renters’ experiences, collecting about 1,000 survey responses in New York bars. There are more solemn settings for market research. A bar at least has the advantage that a stranger can decline the conversation without scheduling a follow-up meeting. The experiment put the founders in direct contact with people who had to deal with rent every month.

The business subsequently moved toward the point at which someone becomes a renter. Feedback from prospective brand partners helped direct attention to move-in, and conversations with landlords exposed problems in leasing. The payment app led them to a different place in the same relationship.

That change gives the early story its shape. Fixing the recurring task was one possibility. Working on the decision that starts the tenancy became another. The first product had supplied an entrance to the market; it did not dictate where the company had to remain.

The question at the end of the form

Carroll’s 2022 account of why he started Findigs laid out an ambition beyond faster paperwork. He wanted people to see homes they qualified for, receive a quick decision, and have a dependable move-in date. Booking a hotel supplied his comparison for the experience he hoped renting could eventually offer.

That is an aspiration rather than a description of every rental transaction today. Its appeal lies in the sequence. A person should be able to understand what happens next. Finding a listing, submitting an application, and preparing to move ought to connect, instead of feeling like separate negotiations with separate clocks.

For Carroll, the product had to address both sides of the relationship. A renter wants access and clarity. A property manager needs reliable information and a process that can carry a decision through. His argument makes empathy part of the design problem: a team needs enough perspectives to question what feels fair and straightforward to different applicants.

By June 2024, Findigs had announced a $27 million Series B led by Nyca Partners and introduced DecisionAssist. The offering combined automation with specialist support, bringing screening and decision guidance together. The announced product included multilingual assistance and options for underbanked applicants. These are practical details in a business whose result is experienced by people with different circumstances.

The current platform describes its outputs as approval, approval with conditions, or decline. That small list carries the weight of the application. A document can contain information without resolving the person’s next step. Carroll’s focus increasingly rests on completing that step, with the decision itself becoming the thing the business sells.

“If people aren’t comfortable challenging the CEO, something is broken.”

Steve Carroll, April 2026

The CEO needs an answer, too

Carroll has described another kind of gap: the distance between what Findigs promised a new client and what it could deliver when the client went live. Growth made that gap visible. Signing an agreement and being ready to serve it were arriving at different speeds.

His response was to rebuild onboarding. The detail matters because it places responsibility inside the company. A business that asks customers to trust its decisions has to make its own promises carefully. A launch date is easy to put on a calendar; readiness requires work before that date arrives.

In his account of leadership, weekly office hours provide another mechanism for correction. Anyone can come, without an agenda. A salesperson can discuss a deal that went wrong. An engineer can push back on a product choice. The person with the CEO title remains available for an argument.

There is a particular logic to that practice in housing technology. The work reaches beyond the people in the meeting. An applicant may experience the consequences of a product choice without ever knowing who made it. Giving employees room to challenge that choice brings an additional perspective into the room before the consequence reaches the applicant.

Carroll’s advice to other founders also includes keeping relationships distinct from transactions and staying willing to move beyond the first product. Together, those ideas explain a recognizable tension in his story. He values a long partnership while permitting the business built around it to change. The continuity belongs to the people and the problem; the product still has to earn its place.

What he asks when he hires

On LinkedIn, Carroll has written about more than 2,000 interviews conducted while building the Findigs team. Looking back through notes on strong performers, he found a recurring feature: they had asked good questions. He describes a startup as a place where asking the right questions constitutes a substantial part of the work.

That observation returns the biography to the habits he associates with Colby: listening, speaking clearly, and responding when a conversation changes. These are modest skills to put beside a technology company’s ambitions. They also happen to be useful when the person across the table knows something the founder does not.

Carroll’s interests outside work add a few more points of texture. He has described himself as an avid bridge player and spoken about his rescue dog and helping foster animals in New York. They are small details, but welcome ones. A person’s life need not consist entirely of evidence for why he was destined to become a CEO.

The bridge table need not be recruited into a theory of underwriting. The dog can remain a dog. In a profile full of applications, revenue, and decisions, there is some pleasure in letting a hobby occupy its own corner. It makes room for the person alongside the professional argument.

A bigger company, an unfinished task

In June 2026, Findigs announced a $32 million Series C led by RPM Ventures, bringing its reported total funding to $80 million. The stated plans included advancing the decisioning platform, expanding affordable-housing capabilities, and launching Rent Guarantee products. Each extends the company’s work further into the rental relationship.

The current company overview puts its network at more than 500,000 rental units. That describes the reach of the platform across operators, rather than homes owned by Carroll or Findigs. In 2026, Carroll also received recognition from NYREJ’s Ones to Watch and Inman’s Future Leaders in Real Estate.

Those milestones locate the business at a different scale from its early renter surveys. They leave the original question intact. When someone applies for a home, what information is needed, who takes responsibility for the answer, and how long does the person wait?

Carroll encountered that question as a renter after learning to look at housing through finance. He brought a college friend into the attempt to solve it, changed the product when the opportunity moved, and later changed the company’s onboarding when its promises needed firmer support. The path contains revisions as well as milestones.

An approval is a small word with a large consequence. On one side sits a company trying to make the process work. On the other sits someone who wants to know whether to book the moving van. Carroll’s working life now takes place between them.