The first time Gavin O’Connor left Dix Hills, a small Long Island town about an hour from New York City, it was mainly for a change of scenery—and to further his education.
At Baltimore’s Loyola University, O’Connor got plenty of both: four years in a diverse and dynamic city; and a marketing degree he knew would come in handy.
“Where I lived, it was half crabcakes and football, and half ‘The Wire’,” O’Connor recalls, referring to the groundbreaking HBO crime drama, which takes place in the city. “I had a chance to play club lacrosse and experience a part of the country I wouldn’t have otherwise. It was a great experience.”
After graduating in 2012, O’Connor moved back to Dix Hills. His first job was selling ads for Yellowbook—producer of the Yellow Pages, the massive business directories once delivered to people’s doorsteps—at a time when the company was transitioning to a digital enterprise.
It wasn’t easy. Or much fun.
When Superstorm Sandy wreaked havoc throughout the mid-Atlantic later that year, O’Connor quickly discovered just how difficult the business could be.
“When you’re working out of your car and knocking on people’s doors with a book that’s been sitting out in the rain for months and trying to sell them ads in it—that’s pretty rough,” O’Connor laughs. “What it taught me was to always be wary of being pitched sales jobs by people who only care about sales. So that was a good lesson.”
Jaded but undeterred, O’Connor went to work for his stepdad, who owned a successful elevator-parts company in nearby Farmingdale. Before long, he was handling everything from sales and marketing to overseeing warehouse operations.
For O’Connor, the sheer range of responsibilities—crafting email campaigns, interfacing with clients, conducting inspections, ensuring timely deliveries—proved invaluable. But it was the experience of working with so many personalities that left the biggest impression.
“It definitely taught me how to communicate,” O’Connor says. “Having to deal with different people, different expectations, different demands: It’s a really good skill to have.”
At a Crossroads
While he enjoyed the work, after six years, O’Connor realized that mixing business with family (his mom was the company accountant) made for a challenging dynamic.
It was around this time his struggles with substance use took a turn for the worse. During his brief stint in rehab, a doctor recommended seeking long-term treatment options outside of New York—somewhere close enough to home, but far enough away to give him the space he needed to address his health.
“I heard great things about the sober community here in Maine—a lot of success stories,” O’Connor says. “I’d never been to Maine. I didn’t know a single person here. But I was willing to take a chance. And I’m glad I did.”
In September 2019, O’Connor moved to a sober-living facility in Portland. His first three days were spent at the library, applying for whatever job openings he could find. The following week, he got a call from Sean O’Reilly, director of sales for Trueline.
“I’d applied to so many jobs that I couldn’t remember what Trueline was off the top of my head,” O’Connor recalls. “But it became clear in talking to Sean, and later with Haj, that this would be a good fit for me—and the right environment.”
Home Away From Home
Joining a seasoned Vanguard team, O’Connor quickly found his groove. And while the clientele was different than any he’d worked with—Ivy League graduates; Fortune 500 attorneys; people whose professional philosophies were as varied as the companies they worked for—the role felt familiar.
“For me, the thing I enjoy most hearing people’s perspectives on their positions: what excites them, what they’re passionate about. There’s always a lot of nuance there,” O’Connor says. “It can be really inspiring.”
Just as O’Connor was settling into his new role—and Trueline’s welcoming culture—the COVID pandemic forced everyone to adjust on the fly. As was the case across the company, that first month was a challenging one for O’Connor. That’s when Trueline’s culture really kicked in.
“It was a struggle at first, for sure,” O’Connor says. “But then people started reaching out with words of encouragement: Sean, Nick Randall, Matthew Warner, Julianna Roche and Matt Schwach. Everyone stepped up. That’s when I realized that the culture here extends outside the office. That’s a rare thing.”
While his first summer in Portland hasn’t gone quite as expected, O’Connor is keeping busy: going to the gym, playing spike ball with friends (if you don’t know, check it out; it’s ridiculously fun) and enjoying the area’s many beautiful beaches.
More importantly, he’s found a home—and a community he can count on.
“When I came here, I was really down on myself, not knowing where my life was going,” O’Connor says. “To come to a company where I can enjoy the work, make good money and be with a great group of people—it’s something I’d have had a hard time picturing a year ago. But here I am.”
Most memorable lacrosse goal you’ve ever scored: I played defense, so there weren’t a lot of goals, but beating Navy—the number one club team in the country—during my junior year at Loyola was really memorable.
Strangest place you found a phonebook: Restaurant-owners using them as booster seats at their tables. Which was the only thing they used them for.
Favorite local beach: Willard Beach
Is it “on Long Island” or “in Long Island”?: On Long Island.
Best character from “The Wire”: Omar Little.