Sign in front of the Waitsfield office.


In a tradition-minded state like Vermont where long lineage is revered, few businesses can trace their origins farther back than Jamieson Insurance of Waitsfield.

“We think that someone was selling insurance from the family farm in 1828,” says Jon Jamieson. “And we have proof that they were doing so by 1865.” That makes him the seventh generation to run the family business, which he took over in 2003 and has grown to include three offices and 12 employees. The agency’s history, commitment to service and community involvement have made Jamieson Insurance one of most respected and successful in central Vermont.

That doesn’t happen by accident. In this era of “virtual receptionists” and “support” that really doesn’t, Jamieson Insurance clients get something that’s increasingly rare: prompt, satisfying service provided by real people for whom the work is far more than just a job. “Personalized customer service and genuine caring are company values,” Jamieson affirms.

That time-tested approach has served clients, associates and the community well for decades. But Jamieson knows that the only constant in life – and business – is change.

“There is disruption in our industry,” he says. “Google and Amazon both are looking into insurance.” That’s concerning enough, but competitors like, with vast resources and data access difficult for local agencies to match, are already up and running. “It’s David and Goliath all over again,” Jamieson points out. “The retail industry is already suffering death-by-Amazon and that, for better or worse, is what the future may hold for other sectors. To survive, independent insurance agencies need to evolve.”

Jamieson Sponsored 2
Insurance as a family affair, the Jamieson family in the Warren Fourth of July parade. Jon, lower left, and Dick, standing.

Evolving, in this case, meant two key things for the agency and, equally important, for its clients. One was accessing resources and efficiencies to compete in the fast and furious 21st- century environment. Just as crucial was continuing to be a client-focused, local business defined by its associates’ passion for caring and personalized service.

It took almost a year of diligent due diligence, during which Jamieson examined and eliminated many options. But persistence paid and eventually he found what he was looking for: a national enterprise dedicated to partnering with entrepreneurial local brokers who deliver old-fashioned personal service. That last statement, in fact, comes verbatim from the website of the Hilb Group. It would be easy to dismiss such a claim as the empty promise of hype – too good to be true – but Jamieson’s detective work revealed that it was both good and true.

“What I heard, over and over,” Jamieson affirms, “was that Hilb shares the single most important core value that we have embraced since day one: total focus on our clients.”

Jamieson Insurance
The Waitsfield office.

The more he learned, the more Jamieson liked what Hilb would mean for his agency and its clients. Joining forces with the company meant access to national-scale assets: human resources, IT, training, software, research and development – all of which dovetailed perfectly with optimizing client service. And it would link Jamieson Insurance with Hilb’s nationwide network of like-minded local agencies, a bottomless fount of collegial expertise and experience in agencies just as client-centered as Jamieson. Finally, the best-of-all-worlds arrangement would allow Jamieson to maintain an ownership interest.

The joining of forces became official in July and Jamieson could not be more pleased. “This is a huge win-win. We keep serving clients our traditional way in our own community while leveraging everything a national industry leader like Hilb offers. That means security for associates, continuity for clients and stability for our local economy as well.”

One last question remains, though. What does all of this mean for the company’s principal and namesake?

“That’s easy,” laughs Jamieson. “My roots are generations deep. I love Vermont, the Mad River Valley, and the business we’ve built here. I’m not going anywhere.”