25-Year Anniversary Provides Connolly Group Opportunity to Reflect on Family Legacy


25-Year Anniversary Provides Connolly Group Opportunity to Reflect on Family Legacy

On the surface, the Connolly Group is professional and serious, focusing on business and specialized insurance, estate planning, and working closely with client legal and accounting advisors. Their work requires unwavering attention to detail and confidentiality so they must practice restraint and regimental organization every day.

But underneath it all is a father and son who’ve built a team that feels so much like family no one ever seems to truly retire. The workplace atmosphere is cheerful and welcoming, and there’s a whole lot of heart in what they do. It’s why their clients keep coming back and their employees couldn’t imagine working anywhere else.

As Shayne Connolly celebrates his 25th year with Connolly Group, he has a lot to be proud of, but he’s too humble to pat himself on the back. Instead, he credits the support of his wife, Lynn, children, Rylee and Matt, and his father, Steve, for his success.

“This milestone has me doing a lot of reflecting and I know that 25 years and what Connolly Group has become is no small feat, but I owe it all to my dad, my family, and our team,” Shayne said. “I wouldn’t be where I am without them. We are a small company that does big business, and we have the confidence of a great deal of people in a world of other options, but I think it’s because we’ve earned their trust and they know we’ve really put our all into what we do.”

Steve Connolly, Shayne’s father, entered the life insurance industry in 1983 as a Sun Life Advisor. He was the first advisor on PEI to receive the Certified Senior Advisor (CSA) designation and was inducted into the Sun Life Hall of Fame, which is a significant recognition and the highest accomplishment in the industry. In 1998, he struck out on his own, forming the Connolly Group. Always thinking ahead, he was worried about succession planning and convinced Shayne to join him. He didn’t have to try very hard.

“My dad was instantly successful in the business and a fabulous mentor, not just to me but others too. I’d been observing him over the years so working with him was a natural progression,” Shayne said. “I learned a bucket load from him, but I also recognized the opportunity for financial stability, so it made sense for my family.”

Though he originally made the move for financial reasons, working at Connolly Group quickly became a passion for Shayne and he helped expand and transform the business. Over the years, they grew from 25 group insurance clients to close to 300.

“We are consistently trying to innovate and provide solutions for people that are outside the box and not just the easy path because we want the best for our clients,” Shayne said. “We really do care.”

That attitude extends beyond the business. Shayne and Steve spend a lot of time volunteering, donating, and giving back to the community.

“Dad instilled that in me from the beginning so to me it’s just part of the gig,” he said. “You can’t just be worried about your employees and your business, but the community you live in too. It’s something that just rubbed off on me and I see that in my children as well. It’s just in our nature, I guess, because it’s what we’ve always done.”

It’s not surprising to Steve that Shayne is crediting everyone else for his 25 successful years with Connolly Group. He always puts others first, and that’s the case with clients too.

“It was my very good fortune that Shayne chose to work with me to grow our business and help provide the best possible service to our valuable clients,” Steve said. “When I was struck with a serious health issue in 2007, Shayne was well prepared to assume a leadership role. With 11 years of experience in our industry, it was in good hands. I will forever be grateful for his choice to return home and become a leader in our field.”

Steve, who still works with Shayne to this day, said he couldn’t imagine Connolly Group without Shayne. 

“I’d just like to say, happy 25th anniversary in our business, my son,” Steve said. “You make me so proud daily.”
To learn more about Shayne, Steve, and the Connolly Group, visit: https://www.connollygroup.ca/our-team/

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