Kevin Denny – LendingTree

Years before he ever reviewed a contract or briefed a regulator, Kevin Denny spent his days sitting across from older adults, walking them through cognitive tests and asking about their lives. As a research assistant in a brain imaging lab at Duke University, he was part of a team studying functional MRI data in older adults with early Alzheimer’s disease and late-life depression. The science was demanding, and Denny admits it wasn’t always his strong suit.

Kevin Denny | LendingTree | Assistant General Counsel

“I was probably a little in over my head on the science side,” Denny says. “But talking with people, running through their histories, listening to what they had to say — that part I loved.”

That distinction mattered. The lab work taught Denny that he wanted a career built around people and communication, not just data. He didn’t grow up around lawyers and had no built-in roadmap toward law school, but he found one anyway, largely by accident. At the time, he was living with a close friend from undergrad who was attending law school at UNC. Night after night, his roommate came home with stories about cases, cold calls, and legal arguments, and Denny began to recognize something familiar in them.

Finding a fit for the analytical mind

“Hearing him talk about his cases, I realized that’s how my brain already worked,” Denny says.

He went on to the UNC School of Law after earning undergraduate degrees in political science and psychology from UNC Chapel Hill. From the start, he gravitated toward litigation. First-year law school immersed him in fact patterns and competing arguments, and he liked the exercise of picking a position apart as much as the answer.

“I liked taking a fact pattern, seeing where the strong arguments were and where they’d fall short,” Denny says.

After law school, he clerked for a federal judge in Greensboro for about thirteen months, reinforcing his instinct for litigation. From there, he joined McGuireWoods, where he spent roughly 6 years building a financial services litigation practice. He handled matters under major consumer finance and regulatory statutes, including the Fair Credit Reporting Act, the Equal Credit Opportunity Act, the Dodd–Frank Wall Street Reform and Consumer Protection Act, and the Telephone Consumer Protection Act, as well as related government investigations. Denny credits the firm with shaping the lawyer he became, even as he sensed, four or five years in, that the partner track wasn’t where he wanted to end up.

A courtroom foundation, then a different front

That realization didn’t come with a plan attached. It came instead with an opening: a regulatory attorney role at LendingTree, the online marketplace connecting consumers with lenders and other financial service providers across products, including personal loans, mortgages, credit cards, and insurance. The subject matter overlapped closely with what Denny already knew from litigation and government investigations, but the vantage point was different. Rather than stepping in after a dispute had taken shape, he would help the business make decisions before problems became lawsuits or government inquiries.

“I wanted to be part of the conversation before a problem became a lawsuit, not just cleaning it up afterward,” Denny says.

Denny joined LendingTree in September 2021 and moved into his current role in February 2024. Today, he is one of five lawyers on a legal team within a broader group of compliance and contract professionals reporting to the general counsel. He and one colleague handle the bulk of the company’s regulatory and compliance work, while others focus on litigation, contracts, and employment. When a new product idea or business initiative surfaces, Denny is usually one of the first calls: can the company do this, what regulatory risk does it carry, and what needs to be built into the process before launch. Because LendingTree operates in every state and touches heavily regulated products, that question comes up often, and Denny works closely with the company’s litigation attorney whenever a regulatory issue intersects with a legal dispute. He also supports the compliance team’s marketing review work, offering a second set of eyes before campaigns go out the door.

Adjusting to that environment took some getting used to. A large firm comes with layers of administrative support and has more attorney resources to handle specific matters; in-house, much of that falls to a small team working things out itself. What Denny didn’t necessarily expect was how much he’d enjoy the shift. Law firm life left him researching and writing independently for long stretches. In-house work put him in regular contact with business teams, compliance professionals, product managers, and marketing colleagues who don’t share his legal background, and translating regulatory complexity into something they can use has become one of the most rewarding parts of the job.

Learning as the price of admission

Nowhere has that adjustment been more constant than with privacy and artificial intelligence. Denny didn’t handle privacy work at his old firm, and he didn’t expect to grow into what he now half-jokingly calls a privacy attorney. His responsibilities grew after his manager, then deputy general counsel, was elevated to general counsel and needed someone to absorb the privacy portfolio. Denny stepped in, earned a certification through the International Association of Privacy Professionals, and has kept up with the field through annual conferences as data privacy and security become more central, especially as AI reshapes what information companies collect and how they use it.

AI itself has become one of the busiest corners of his practice. Internally, Denny has helped build policies and guardrails around tools employees want to use, including a note-taking feature that required weeks of discussion with senior leaders and pilot testing before rollout. Externally, LendingTree is constantly exploring customer-facing AI applications, from chatbot tools that answer questions about mortgage rates to features that could help consumers compare offers or make sense of an existing loan.

“It’s a little bit like drinking from a fire hose,” Denny says of the pace of AI-related work.

That work became particularly tangible when LendingTree set out to build a ChatGPT plug-in that allows consumers to explore mortgage and refinance rates through a conversational experience. The project moved quickly, with Denny working closely with product, engineering, and compliance teams through the final stages of development. His involvement stretched from reviewing designs and mockups to understanding the tool’s methodology, developing necessary disclosures and determining how to present them without cluttering the user experience, and testing how the plug-in responded to a range of questions. For Denny, the project captured the kind of legal work that drew him in-house in the first place—not reviewing a finished product from the sidelines but working alongside the business as it was being built.

Asked where that leaves him, Denny doesn’t claim to have it mapped out years ahead. What he has instead is a rhythm.

“I don’t have a five-year plan,” Denny says. “But year to year, I set some goals — areas I want to grow in, people I want to work with. Maybe that’s just how it works when your team is lean.”

It’s a fitting way to describe a career that started with a young researcher more curious about people than about data, and has led, years later, to a lawyer who still measures success the same way: one conversation, one problem, one year at a time.