Mike Connolly had successful careers in sales at big-name, Boston-area companies like CarGurus and EverQuote. But after experiencing burnout and a loss in his family, Connolly stepped away from his career to focus on giving back.
He founded Pay Forward Coaching last year, which provides free career services to those who might otherwise not have access. And even more recently, Connolly joined the dog apparel brand K9Wear Inc. as president. He’s not taking a salary, and signed on for equity in the startup and milestone bonuses.
Connolly recently spoke to BostInno about his career transition, finding new purpose in his work and K9Wear’s fashion-empire plans.
Moments of transition
Connolly is a Boston guy. He grew up in South Boston and attended a Catholic elementary school before winning a scholarship to Milton Academy.
“Amazing experience. I think it just kind of just changed the trajectory of my life,” Connolly said.
Connolly studied computer engineering at Tufts University, but quickly transitioned to sales at companies like PAETEC Holding Corp. and Experian Data Quality. Then he found himself at CarGurus in 2015. He considers this move his second life-changing moment. Connolly said CarGurus was still pretty early with less than $100 million in annual revenue when he joined as director of sales and dealer relations.
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CarGurus went public in 2017, and Connolly was promoted to vice president of sales and service in 2018. That same year, his father died unexpectedly six months before his planned retirement.
“That really struck a chord with me, I’m working incredibly hard, I’m putting money away, I’m kind of banking everything for the future. But obviously we’re not guaranteed a future,” Connolly said. “That made me really think, how am I spending my time? If I die today, am I going to look back and say I lived my life the way I wanted to? At the time, the answer was 'no.'”
After experiencing that loss and realizing he was suffering from burnout, Connolly said he started thinking more about charitable work and spending time on mentorship. In 2020 Connolly moved to EverQuote and became a senior vice president of sales and customer success. Working remotely during the pandemic wasn’t bringing him joy, and he left EverQuote last summer. Not long after, he started thinking more about the startup he invested in back in 2019.
Building a canine fashion empire
Ironically, Connolly’s dog refuses to wear clothing. The one time Connolly tried to put a Christmas sweater on his then 2-year-old dog, he refused to wear it. It didn’t really fit right and the garment went down his legs, restricting his movement.
But Connolly saw potential in a dog apparel brand founded by James Straggas, a former coworker at Experian. The pair got drinks and Straggas explained that K9Wear’s clothes fit to the harness, not the dog. That way people can get a harness to fit once and have many different outfits to fit that harness. Connolly said this solves for fit and comfort.
“Most dogs, including mine, are used to wearing a harness. And then you’re fitting the clothes onto the harness — the dog doesn’t know they’re wearing anything. It just feels like the same harness to them,” Connolly said.
Connolly started as an investor at K9Wear. But after a Series A partnership deal with Frank Cammarata, a New England businessman and principal and CEO of The Enjoiya Group, which was previously Camtrade Footwear, Connolly agreed to join the team and help them go to market.
He said "volunteer" is too strong a word to describe his involvement in the startup — he gets equity and milestone payments. But rather than spending the new investment on his salary, Connolly said he’d rather see it go to product development, R&D and other expenses.
In 2024, Connolly said they’re aiming to do $3 million in gross revenue and be a $10 million business by 2026. The company is working with Tommy Bahama and Connolly said he wants K9Wear to have partnerships with at least two more premium fashion brands.
K9Wear has a showroom in New York City but about half of its team members are in Massachusetts, including Connolly, Cammarata and Straggas.
