Monadnock Profiles: For Dick Hill, his love of Jaffrey runs deep

  • Dick Hill, owner of Hill Family Insurance, is set to retire at the end of this year and hand off the business to his four kids, including his oldest son Nick. Staff photo by Tim Goodwin

  • Dick Hill, owner of Hill Family Insurance, is set to retire at the end of this year and hand off the business to his four kids. Staff photo by Tim Goodwin—

  • Dick Hill, owner of Hill Family Insurance, is set to retire at the end of this year and hand off the business to his four kids. Staff photo by Tim Goodwin—

  • Dick Hill. Staff photo by Tim Goodwin—

Monadnock Ledger-Transcript
Published: 10/28/2019 10:19:12 AM

It’s clear from talking to Dick Hill that he takes great pride in his hometown.

Not only did Hill grow up in Jaffrey – as did his mother and maternal grandmother – but it’s where he met his wife Katherine, raised his four children and operated his insurance business for the last 34 years.

Outside of college and three months living in Boston, Hill has spent the rest of his 67 years in the town best known for Mount Monadnock and a longstanding tradition of great high school basketball. And he’d have it no other way.

“Very proud of this town, and I think it’s a phenomenal place to raise a family,” Hill said. “Its been a blessed life.”

Hill said he never wanted to live anywhere else and didn’t enjoy his time in the city. It helped him gain an even deeper appreciation for where he came from and realize that everything he ever wanted was in the place he knew best.

It was something he tried to instill in his kids, and it worked. All four, Nick, Sam, Abby and Liza, have stayed to raise their own families in the town where they grew up, and selfishly for Hill it means he has the unique opportunity to be close to all 11 of his grandchildren. And with each one of his children deciding to join the business – Hill Family Insurance – it gives special meaning to the name he picked out many years ago. 

“I bribed all four of my kids to stay in Jaffrey – all with jobs,” Hill said.

With Hill set to retire at the end of the year, his children will take ownership of the downtown mainstay.

“It’s a dad’s dream to have your children want to work for the family business,” he said. “Because for me, family is No. 1.”

Running a small town insurance company hasn’t always been easy. He started in the industry 45 years ago, spending the first decade of it working for three different agencies in the area. But when Cournoyer Insurance went up for sale, Hill knew it was time to be his own boss. It didn’t come without a big time commitment, something he never would have been able to do without the support of his wife.

But it was important to Hill to make an even further investment in the future of Jaffrey – and at the same time be his own boss. 

Hill knows he’s in a business that most people would rather do without.

“Nobody likes insurance,” Hill said. “But the key to being successful is being there when something happens.”

That meant phone calls at all times of the day and night, long days in the office and interruptions at the most inconvenient moments.

“Many dinner were interrupted with phone calls,” Hill said. “Because it’s 24/7, but the reward of owning your own business is second to none.”

It was all worth it, especially now with his children carrying on the tradition that Hill worked so hard to create.

“I still have customers who have been with us for 30-plus years,” he said.

While Hill has enjoyed his career as small business owner, his true passion has – and always will be – sports. Growing up, he played soccer, basketball and baseball. He was a good athlete at Conant and went on to play college soccer. But there was something about coaching that captivated him.

“I wanted to get kids outside and experience all that sports were about,” he said.

It started when he was 17 with a mission to bring Little League baseball back to Jaffrey. There hadn’t been a league in town since he was 12, so he went to the selectmen, got approval to use Humiston Field and provided an opportunity for kids in town to play.

“That was 1969 and I’m proud to say its been running consistently since that day,” Hill said.

When his kids were old enough to get involved, that’s when Hill really dove head first into coaching. He started a Saturday morning basketball program in 1983 and ran it for 14 years. He did the same thing for soccer and went on to coach travel basketball teams.

“I hope I impacted the kids of this town,” Hill said. “And it’s neat now to see kids I coached, stay in Jaffrey, have a family and now they’re kids are playing sports here.”

In 1988, along with former Peterborough Recreation Director Beaver Jutras, Hill created an 11 and under AAU basketball team, something at that time was unheard of in New Hampshire.

Sports was his life and was fortunate that all four of his children shared that passion. They spent many nights at local field and gyms, traveled to tournaments all over New England. He coached middle school basketball and the final three years of his coaching career came as the Conant girls soccer coach, getting the opportunity to be there for his youngest Liza’s final three years of high school.

He likes to think he made enough of an impact on his children that they wanted to get into coaching. All four have done it with their own children, while Nick spent a number of years coaching boys soccer and girls basketball at Conant. Watching his son win a state championship from the stands still remains one of Hill’s greatest sports memories.

He’s been a Boston Red Sox season ticket holder for 20 years and is a die hard New England sports fan.

“Last year was just the best,” Hill said.

In January, the two high school sweethearts will head down to Marco Island for a week to check out the sights. Hill will have a little more free time by then.

Hill met his wife in kindergarten and the two started dating senior year of high school. They’ve now been married 44 years.

They enjoy doing little trips like that. They always took the kids to Disney every other year and have been known to head down to the Bahamas for a short trip from time to time. They like the warm sunshine in the winter months and it doesn’t hurt there’s a casino down there. Hill enjoys taking day trips to Foxwoods to play the slots, for the thrill and excitement of it.

Hill was one of the original board member of TEAM Jaffrey and helped organize and run Scarecrows on the Common for its first 10 years. He served on the St. Patrick’s school board for two years when Nick went there for his first two years of school. Someone asked and he couldn’t say no.

He never wanted to get into local politics, but always felt if he had the chance to give back to his hometown he would. And over the years, Hill has done just that, quietly doing what he could to help improve the community he cares so deeply for.

Because in the end, Hill couldn’t imagine living anywhere else but the town of Jaffrey. And even as he gets set to retire and see some big changes in his life, leaving his hometown is not anything he would ever consider.


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