2021 Broker of the Year finalist: Tom DiLiegro

Tom DiLiegro’s career path is a testament to the impact an employers’ health plan can have on employees and their families.

Tom DiLiegro resisted his calling to the benefits industry until his eyes were opened to a new breed of broker-advisor that preached greater benefits for employees at a lower cost for employers. (Photo: Kevin Garrett)

The 2021 Broker of the Year will be announced at the BenefitsPRO Broker Expo, August 16-18 in San Diego. The winner will be further profiled in our September issue. 

The inspiration for Tom DiLiegro’s ultimate career choice lay hidden in his heart for years. He was unaware of its power, although it was pushing him in a certain direction. Then someone who would become a coach, mentor and friend unearthed and presented it to him.

In the realm of “aha” moments, this one ranks way up there.

DiLiegro, a nominee for Broker of the Year, is principal advisor at Benefit Advisors of Charleston, S.C. There, he guides his clients through the tough choices confronting those who are willing to cast off traditional health plans and create, with DiLiegro, customized plans based on the concept that an employer’s health spend is an investment rather than a liability.

Related: Employees as assets, the C-suite as investors

“It takes a lot of work to understand the options he’s talking about,” says client Chris DiCampli, co-owner, Preferred Home Services in Charleston, S.C. “I don’t like to talk about insurance. But Tom made me understand, and we changed it. We just renewed on June 1, and this was the most effective plan, by definition of response by employees, we’ve had. Essentially it was seen before as a tax taken out of their paychecks. Now they see it as a benefit.”

A native of Andover, Mass., DiLiegro grew up in a working-class family with four older siblings. His dad worked for a local grocer. Things were tight, and got tighter when his father became ill and eventually passed away. But the family was able to make ends meet, largely thanks to the health insurance coverage provided by Star Market.

Photo by Kevin Garrett

“I honestly did not make the connection between my family story and what was going on with insurance, why I was drawn to it.”

After DiLiegro graduated from Merrimack College with a BS in health science, he fell in love with a woman from Charleston. Goodbye New England, hello Old South! There he got an MBA and, still uncertain about a true calling, entered the working world with a Charleston-based third-party administrator.

“It was a way to combine my interest in health care with my acumen for business,” he says. “But once I was hired, they said, ‘You gotta get your insurance license.’ I thought, ‘I have an MBA and I’m selling insurance?’ But that’s the way it went.”

Insurance had an inexplicably strong hold on him. He fought it, believing it was “a rigged game.” He even took a job with a hospital system in Charleston, “which was ten times worse than selling insurance,” before returning once again to insurance.

But times were changing. The old ways were being challenged by a new breed of broker-advisor. They preached greater benefits for employees at a lower cost for employers. DiLiegro was captivated.

It was at that critical moment that he turned to Q4intelligence, a training/coaching/marketing firm. Working with Q4i’s Wendy Keneipp and Kevin Trokey, DiLiegro searched for a way to connect in a deep way with prospective clients.

“We were helping him work through his insecurities about having conversations with people that are different. He had this traditional pitch but it wasn’t working for him. He couldn’t connect with what he wanted to say,” she says.

During one of their many conversations, Keneipp suddenly realized it was the story of his father that was subconsciously driving him to protect employees. She pointed out that his family survived the death of the father because of the company insurance.

“I honestly did not make the connection between my family story and what was going on with insurance, why I was drawn to it,” he says.“Wendy showed me it was my dad behind it all the time. A lot of what I do now, I owe to her,” DiLiegro says.

Once he saw it, he was able to overcome his client discussion fears.

“Now, he’s so open and willing to have those conversations, to get vulnerable. That is what makes him so powerful in his work with people,” Keneipp says.

His new style finally convinced Preferred Home Services’s DiCampli to take the plunge into a new plan design.

“He came to me first, as a customer,” DiCampli recalls. “We stayed in touch, he started talking to me about my health plan. I hate talking about insurance, kept putting him off. Finally one time he said, ‘I’m trying to find creative solutions for your plan. I want to help you.’ He said, ‘Let me explain how it works.’ He convinced me to try a high-deductible HSA plan for us. it’s essentially an investment. And it’s been beneficial for us. I actually got a check back from it last year.”

DiLiegro is always available for the plan members of Preferred Home Services, DiCampli says, and no matter is too small for him to take care of.

“His level of service is out of this world. We had a child with a terminal illness, employees with cancer, heart problems. Every time he gets to know these people. He’ll get a call from an employee who doesn’t understand why a hospital bill is so high, and he takes care of it. I know he doesn’t have to do this stuff. He just cares tremendously.”

No one can put into words why insurance matters to Tom DiLiegro better than himself: “I am the embodiment of an impact an employer can have on their employees and their families through offering employer-sponsored insurance benefits. My father had a terminal illness and had access to affordable, world-class health care, partially financed by his employer. That employer was a lifeline to my family and we will be forever grateful for the benefits they had for their employees.

“My goal is to propagate my experience to as many organizations and their employees in the most cost-efficient manner possible.”

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