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 Jon Jamieson’s grandmother’s family settled in Waitsfield on the heels of General Wait in 1798 as dairy farmers.

“We’re pretty sure someone in the family was selling insur­ance from the farm by 1828, but we can prove they were by 1865 (the year the Civil War ended),” said Jamieson, the seventh generation of his family to sell insurance in the Mad River Valley (and now beyond).

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Farming was hard and after a nearly catastrophic accident involving a collapsing pile of sawdust and the herd of Jer­sey’s being decimated by bru­cellosis, the Jamieson family sold the farm to the von Trapps and eventually settled full time into their new calling - selling home, auto and business insur­ance.

“Most of our earliest custom­ers, after the Civil War ended, needed insurance for things like homes and farms. Fire and collapse were the biggest threats to property. Liability insurance wasn’t as much of a concern because there weren’t as many lawyers in Vermont!” Jamieson said.

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“One of our first more mod­ern-day accounts was provid­ing the property insurance for a brand new ski area called Sugarbush. We still help Mad River Glen and Cochran’s with their coverage but now insure a wide variety of Main Street businesses, contractors, mad scientists and inventors, hos­pitality ventures, and some of the best brewers and distillers in Vermont,” he said.

Jamieson Insurance is well known for the “insurance guy” shtick, a memorable and fun­ny series of radio ads that run on WDEV, Waterbury’s local radio station. While the ads joke about being obsessed with the details of actuarial tables, premiums and policies, there’s some truth to that. Jamieson Insurance worries about in­surance so its customers don’t have to and is committed to providing local, live and hu­man-powered service to their home and auto insurance cus­tomers as well.

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Since Jon Jamieson purchased the business in 2003, the agen­cy has grown to three loca­tions and 12 employees. In a competitive landscape where consumers have many online and physical places to get in­surance, Jamieson Insurance believes that local customer service paired with the best technology available beats any experience the internet, Costco or national affinity pro­grams can offer.

“Unlike direct companies like State Farm and GEICO, we are independent and local, and deeply rooted in this commu­nity,” Jamieson said.

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“After college I lived on the West Coast but was drawn back here to raise my family where I was raised and to work in this community, contrib­uting as a business owner and volunteer,” he said.

Jamieson serves on the Waits­field Select Board and is past chair of the Mad River Val­ley Community Fund. He’s vice chair of the MRVPD and a board member at North­field Savings Bank. Jon’s latest non-remunerated position is on the governor’s committee that is working on the taxation and regulation plan for legal­ized marijuana.

The same thing that motivates the staff at Jamieson Insurance at work motivates them when they’re away from work, and that is community.

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“Our staff members are cus­tomer-focused and they strive to achieve professional certi­fications. Ten staff members have professional designations that they achieved through rig­orous study and testing. Our company owes everything to community support and, in turn, personalized customer service and genuine caring are corporate values,” Jamieson added.


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