Jay McCloskey has always had a big personality – an outspoken, super-friendly, teddy-bear kind of guy. But one of his most apparent- and arguably most life-defining - personality traits he just can’t seem to shake, is his relentless entrepreneurial spirit.
He started it all with CareVan Transportation in 1984, a very successful non-emergency medical transport company. After nearly ten years, and 5 million (impeccably safe) miles, spread across a fleet of 27 vehicles, Jay was ready for a big change. This time, risk management was the name of the game.
In 1994, Jay started Professional Driver Training Institute (PDTI), becoming Minnesota’s premier driver trainer for most non-emergency medical transportation drivers, taxi drivers and school bus drivers. Most notably, he became the sole trainer for Metro Mobility drivers, who had a fleet of nearly 240 vehicles.
After 10 years running PDTI and nearly 20 years into his transportation career, however, Jay continued to recognize a significant gap in the market – specifically for commercial transportation insurance.
“There was a dire need for an agency in Minnesota owned by people with a solid background and extensive expertise in both commercial transportation and risk management.” Jay said.
At a certain point, Jay just couldn’t ignore the gap any longer. And considering his long history with commercial transportation coupled with a heavy focus on safety, Jay thought, “Who better to fill that gap than me?”
Jay founded Transportation Insurance Professionals (TIP) in 2004 – an agency that provided not only stellar commercial auto insurance services, but also expert help in risk management. The need for these comprehensive services were reinforced by TIP’s immediate success. This success carried TIP through 15 years of significant growth, which allowed Jay to bring all three of his children and their spouses on board - a family business through-and-through.
Synergy Insurance Group
TIP continued to grow rapidly and be very successful, yet Jay – now along with his children Serina, Ian and Terence - couldn't shake his persistent determination for industry improvement. He had recognized yet another gap in the market – a comprehensive insurance agency that could do it all but was also deeply grounded in unwavering honesty and integrity.
“We wanted to be a full-service agency for our clients and to begin offering all types of commercial and personal lines of insurance.” Jay said. “All served up on a sturdy foundation of soaring, steadfast standards.”
Enter Synergy Insurance Group.
In 2018, Jay and his children founded the all-encompassing Synergy Insurance Group (SIG), which subsequently expanded the family’s expertise to all types of insurance – both personal and commercial.
The response has exceeded everyone’s expectations and the excitement has only just begun.
To the Future
Serina Lindsley, SIG’s Service Operations Officer, sees a very bright future for the agency that focuses on excellent service to its clients by ensuring employees are happy and well taken care of.
“For the future of our agency, I see a successful and efficient working environment that promotes the overall well-being of our employees and their families.” Serina said. “I want SIG to be an environment where a diverse array of talented employees flourish and are able to provide tailored, specialized solutions for every client that comes our way.”
Ian McClosky, SIG’s Sales Operations Officer agrees.
“I see our agency continuing to grow, a lot, and rounding out our services.” Ian said. “And as far as for our employees, I’d like it to be a great place to work. I want prospective employees to be knocking down our door to get a job with us.”
But for Ian, it doesn’t stop there. He also aspires to significantly increase SIG’s community involvement.
“I want to feature charitable work front and center to our mission here at Synergy Insurance Group. I want to make sure we are giving back to our communities.” Ian said.
For Terence McCloskey, SIG’s Administrative Operations Officer, protecting clients’ hard-earned money and setting bold industry standards are his cornerstones when looking into the future.
“It is tantamount that we continue to protect the financial interests of our clients, especially during these difficult economic times.” Terence said. “And we will work our hardest to continue to be a standard-setting agency for both our clients and our employees.”
For Jay, he said he heartily supports all his children's bold visions, but most importantly, he considers himself to be the luckiest man in the world to be able to eagerly look to the future with every one of his children by his side.
“I consider it an incredible blessing to work with my kids.” Jay said. “And in the future, when I retire, I know the agency will be in the best of hands.”
Apart we survive. Together we thrive. Trust Synergy.
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Red Wing, MN 55066
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