Devin Wells’ Intriguing Career Path: From Westfield To Westport

Devin Wells did not expect to wind up in a place like Westport.

The son of a 19-year-old mother who immigrated from Portugal, and a 20-year-old Black father, he grew up in Westfield, a working-class town outside of Springfield, Massachusetts.

His parents were great role models. Devin’s mother worked her way up from receptionist to chief operating officer of a law firm — without a college degree. His father is a truck driver. Both modeled hard work, and consistency in their relationship.

Wells was an All-State (and All-Scholastic) basketball player at Westfield High School. He still holds the school’s rebounding record.

He went to local Westfield State University — the first person in his family to attend college — and lived at home, to save money. In addition to classes, he worked full-time at the YMCA.

A marketing internship led to a full-time position senior year. That in turn led to interviews PURE Insurance, focusing on high net worth clients.

Wells won the job, over others from Ivy League universities.

He worked in Charleston, South Carolina for 3 years. When he was named sales marketing manager for Connecticut, he and his wife — a registered nurse at Yale New Haven Hospital — moved to Avon.

Wells traveled all over the state.

Devin Wells, and his wife Victoria.

 He was recruited by Berkley One, handling the Northeast territory. Organizing golf outings at Longshore, he became familiar with the town.

Wells was very good at his work. But, he says, “I didn’t feel I was making an impact on anyone’s life.”

Eighteen months ago, he took a risk. He changed his career path, and became vice president at Howard & Gay. He had met the partners while working at Berkley One.

Devin Wells

Wells calls it “the best decision I ever made. Making clients in Westport is more like making friends. I speak daily with people who were complete strangers  before. We talk about our lives.

“I have clients everywhere. But the ones I have coffee and dinner with are here.

“Where I grew up, people were just trying to get by and survive. There is such a strong sense of community in Westport. I don’t think a lot of places have that.”

Under partners Livy Howard & Willis Gay, the company has always been community-oriented. Wells likes that approach.

The company sponsors Staples High School sports, including football, soccer and basketball, along with other local events.

For Wells, the community feeling is especially meaningful.

“One of my biggest fears coming into high net worth insurance was that my family wasn’t wealthy,” he admits.

“But I never felt that my opinion was not valued.”

Howard & Gay’s recent Client Appreciation Day at Compo Beach — complete with food trucks and a fun vibe — was a chance for Wells to greet clients he’d never met in person.

The Howard & Gay team, at Compo Beach.

“I’m a large man of color,” he notes. “But I never felt unwanted there, or in any room.

“Having that burden off my shoulders is huge. Still, it’s a real issue in a job dominated by white men.”

Wells is enjoying meeting the many Westporters who come from different countries and cultures. This is a town he feels increasingly at home in.

“I plan to be here for a very long time — working, and hopefully living,” he says. “Over the past 18 months, Westport has proven itself as the right place to make a career.”

His story is “not a miracle,” he knows. Still, he says, “I hope other people can relate, and be inspired by it.”

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