Former history teacher ‘accidentally’ becomes benefits adviser

When adviser Derek Winn was 10-years-old, his father underwent open heart surgery, and something his mother said about the situation stuck in his mind: “Do you realize if we did not have good health insurance, we would have lost everything?,” she asked.

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“I’m here in this career today, and that’s what it’s all about,” says Winn, an adviser with Business Benefits Group, a benefits agency in Fairfax, Virginia. “It’s what fuels me today.”

But like so many careers, it was not a direct path. In fact, Winn wasn’t planning on ending up in benefits at all when he first joined the workforce. The former AP U.S. history teacher says he landed in the benefits industry by accident. An introductory phone call with BBG after leaving the teaching profession set Winn on his current path.

Now, at 36, he is one of Employee Benefit Adviser's 2019’s Rising Stars, a recognition to honor up-and-coming benefit advisers.

Winn says he sees definite similarities between his former career and his present job.

“People comment and say, ‘You know, it’s really interesting to make the leap from teaching to what you do now. That must be really different,’ and I say, ‘Not really,’” Winn says. “When you think about what we do, all we’re doing is educating people … that’s the way I think about it. I’m still an educator at heart.”

Winn has a philosophy that he shares with clients, usually when working with parents of older children who are unsure what they want to do for a living. He says becoming a teacher when you don’t know what you want to do is a good tactic.

“In teaching you’re dealing with people, politics and difficult situations, and you have to be organized,” Winn says. “A lot of people have this concept that teachers show up at eight o’clock and leave at three o’clock. But I probably worked as many hours and just as hard teaching as I do in my role today.”

His time as a teacher, Winn says, equipped him with the knowledge and skills needed for life as an adviser. Now his focus, though, is on teaching others about health benefits. One goal he has is helping clients — and their employees — deal with rising healthcare costs.

Employee pay typically doesn’t rise every year in the same way healthcare costs do. When thinking back on his family’s experience and his father’s surgery and then comparing that with today’s market, there is a real possibility that people today in that same situation will lose everything, he says.

“What really fuels me day today is [thinking about] how can we try to make people’s lives better,” Winn says. “How can we help to give them financial security? How can we help companies to lower costs and be able to thrive in whatever industry they’re in?”

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