Avery Insurance – A 27-year-old business development manager reflects on joining his family’s insurance company and modernizing it for the next generation.
A 27-year-old now sits in a familiar chair—one that, for decades, belonged to his grandfather—and the path there has been shaped as much by everyday family moments as by business ambition.
Evan O’Dowd, a business development manager at Avery Insurance, grew up with the company woven into daily life.. He remembers even small childhood moments turning into business lessons: around age 10. when his younger sister lost one of her Webkinz stuffed animals. he suggested selling her “Webkinz insurance” as a playful way to protect against future losses.. That lighthearted idea was his first step into the family business world.
The connection goes deeper than that early episode.. O’Dowd’s great-grandfather started an insurance company, and both of his parents still work there.. Avery Insurance. he said. has been part of his life since birth—showing up in conversation on drives to sports practice and around the dinner table.. While that constant presence never bothered him. he also felt a pull to build his skills beyond the family firm before considering whether to join it as the fifth generation.
Before returning, O’Dowd pursued a career elsewhere.. He left New Hampshire to attend school in Denver. took a stint in tech sales. and then joined a startup in Colorado and later in New York City.. Working in New York. he found himself surrounded by young entrepreneurs and described the experience as both immersive and energizing—learning by being close to people building companies from scratch.
Even as his career progressed outside the family business, the conversation about Avery Insurance never stopped.. O’Dowd said he continued to talk with his parents about the family firm. and that last year he felt the timing was right—not only because of where the business was. but also because his parents needed reinforcement.. He emphasized that they never pressured him to come work there. and that the decision was driven by a desire to make an impact on the family legacy at a moment when his contribution could matter.
When he moved back, the transition wasn’t just professional.. He initially lived with his parents. which meant handling the unusual mix of being their child. their roommate. and their colleague at the same time.. O’Dowd said he respected the work his parents have put into the business because he’s seen it firsthand. and that they have also respected what he learned elsewhere—giving him room to put new ideas into practice.. Still. finding his own place was a priority as he adjusted to a role that came with both closeness and expectations.
His approach to the business centers on change inside a traditional industry.. Insurance, he said, can be antiquated, and he is passionate about modernizing Avery Insurance.. From his perspective. bringing updated thinking is not just about adopting new tools; it’s also about rethinking how the company operates and how it prepares for what comes next.
While work was going well, O’Dowd also missed something he had in New York: the community of peers.. In New Hampshire, he found that same entrepreneurial momentum doesn’t automatically appear, so he started building it.. He said he has been cultivating opportunities for young people. including helping host an event for entrepreneurs under 40 last week. as a way to recreate the kind of peer energy that helped him thrive earlier in his career.
The family company relationship, meanwhile, extends beyond the office and beyond business roles.. O’Dowd described moments when his nearly 90-year-old grandfather—who still visits the workplace—sees him working in the space his grandfather once occupied for much of his life.. For O’Dowd. that scene captures what the job has brought him personally: it’s another way to feel closer to family. even when he isn’t trying to turn the workplace into a family museum.
Not every member of the family is drawn to the same path.. O’Dowd said his sister is not involved in Avery Insurance, and that everyone is fine with it.. Instead. she runs wellness and yoga retreats—something he views as evidence that the family’s business wasn’t her fit. and that she built a career around what she cares about.. His description points to a family dynamic where participation is voluntary rather than assumed.
At 27. O’Dowd doesn’t have children yet. but he said that if he did. he would follow the approach his parents used with their children.. In his telling. their goal was simply for each of them to be their best self—whether that meant joining the insurance company or choosing a different direction entirely.. Running a fifth-generation business, he acknowledged, is not easy, and he doesn’t believe anyone should be pushed into it.
Taken together. his story shows how legacy can work two ways at once: as a responsibility to carry forward what came before. and as a chance to reshape it with skills gained elsewhere.. By choosing to join when he felt ready. building community while he settles into the role. and treating modernization as a core mission. O’Dowd is signaling that the future of a family business may depend as much on independence as it does on tradition.. In Misryoum. the long view of multigenerational companies often comes down to one question: will the next leader step in with enough conviction to honor the past and adjust for the present.
insurance industry family business Avery Insurance business development startup experience multigenerational legacy entrepreneurship community