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mike-umpleby (1)Mike Umpleby, Winston Benefits’ new vice president for employer solutions, says he’ll use his expertise and experience to help organizations implement a wide range of employee benefits solutions.

A native of Columbus, Ohio, Mike now lives in North Carolina, and will concentrate on the Southeastern U.S., with a focus on the retail, health care, manufacturing and hospitality sectors. The former college basketball player and current sports and fitness enthusiast says he’s excited about helping clients drive value in the benefits administration and enrollment process.

Benefits Sales Background

After graduating college, Mike took a sales job with a copier company, where he cut his teeth in the sales world before diving into the employee benefits world at Unum Group. He worked for Unum in both Columbus and then in Charlotte, North Carolina, for nearly four years.

He later worked at AwaysCare Benefits, but found himself back at Unum in 2016 when the company acquired AlwaysCare for its dental-vision operations. He ran Unum’s dental-vision operations in the Northeast for two years, but says he always knew he wanted to return to the Carolinas.

“I had lived for 8 1/2 years here in Charlotte and absolutely built a lot of roots and loved it here,” he says. “I knew I wanted to get back eventually.”

Building Relationships

Mike says that when he was previously selling ancillary benefits, particularly in the dental insurance market, the landscape was saturated with nearly two dozen companies. Even though some major players got out of the market in recent years, he says it often presented challenges.

“The industry still felt somewhat commoditized,” he says. Mike says he’s looking forward to being able to work with organizations on a deeper level, offering them more comprehensive solutions for their benefits needs, ranging from administration and technology to enrollment. He’s also excited about the benefits landscape in the region.

“The South is far more voluntary-benefits friendly,” he says. “It's huge down here; everybody has it. There's a lot of competition, but bringing a company like Winston in that can do everything is a game-changer.”


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Winston Benefits is a Benefits Administration, Enrollment, and Communication company. We provide employers with a technology enabled benefit process in order to help communicate, enroll and administer their employee benefit programs while empowering their employees to make better benefit decisions. Contact us to learn more.


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