Herald Journal - Enterprise Dispatch - Delano Herald Journal
Want to see the full newspaper including all the photos? Check out our online edition here:
Flagship reflects on 75 years
Feb. 16, 2018

By Starrla Cray
Associate Editor

WINSTED – Founded in 1942, Flagship Insurance Services has deep roots in the Winsted community.

It all started with J.J. Sterner, who owned the insurance agency as part of the bank in Winsted. The first employee was J.J.’s son, Richard “Dick” Sterner, and the second was Richard’s wife, Doris.

In about 1960, another couple was hired – Robert and Carolyn Bayerl.

“Now the agency essentially had four employees who were full time,” said Flagship representative (and former owner) Dave Sherman.

Dave has been active in Flagship since 1988, when the bank was starting the process of being sold and separating from the insurance agency.

“I knew Dick Sterner well, and he asked if I’d be interested in buying the agency,” Dave recalled.

Dave officially became the owner Nov. 1, 1989. Although the agency wasn’t part of the bank anymore, it continued to operate out of the bank location downtown until October 1996. Then, it moved to a newly-built facility at 131 6th St. N. in Winsted, where it still operates today.

After exactly 10 years of ownership to the day (Nov. 1, 1999), Dave sold the agency back to the bank. He and his family stayed involved during those years, though. Dave’s daughter, Jennifer Sherman-Stratton, began working at the agency full time in 1998, and purchased it in 2012. Coincidentally, the date she assumed ownership was Nov. 1, just like her father.

Like father, like daughter

In other ways, the histories of Jennifer and her dad are similar. Both graduated from Holy Trinity High School in Winsted, and both were valedictorians. They also both attended the University of Minnesota, where Jennifer earned a degree in business and Dave studied economics and accounting.

“I’m trying to convince [Jennifer] to go for her MBA,” said Dave, who has a master of business administration (MBA) degree from the University of St. Thomas, and a PhD from Pacific Coast University.

“Maybe when my kids are older,” Jennifer said with a laugh. At the moment, Jennifer has plenty to do as a wife, mother of three, and business owner. And, according to Dave, Jennifer is doing “one heck of a job” with the insurance agency.

“Since she took over, she’s increased the value of the agency by 50 percent,” said Dave, who has stepped back somewhat from the business, and spends part of his time in Arizona.

Jennifer said, “When I bought the agency, we had business all over the state, but our target was a 25-mile radius from Winsted.”

Now, Flagship has 24 broker partners throughout Minnesota, as well as a sales office in Edina. The business has been expanding its reach in the Twin Cities, and is poised for continued growth. Dave noted that the industry trend in the past 10 to 15 years has been toward consolidation, and Flagship is open to opportunities to purchase smaller agencies.

Being located in Winsted has helped Flagship keep its costs down, Dave said, adding that the company is recognized as a “gold” agency for having a gross profit margin of 20 percent or more.

Dave and Jennifer attribute much of Flagship’s growth to its employees.

“We’ve been very fortunate,” Dave said. “The secret to our success is not just good employees – it’s excellent employees.”

Many of Flagship’s workers have been with the agency for several years, providing a high level of knowledge, trust, and consistency for clients.

The ‘finest clients’

For both Dave and Jennifer, the best part of their job is the people they work with.

“We have some of the finest clients you are ever going to find,” Dave commented. “The relationships you build go beyond friendships. . . . It makes the job really rewarding.”

Jennifer echoed that sentiment, noting that the relationships with clients is one of the reasons why she decided to take over the business. Originally, she had planned to go to law school to become an attorney, but has found the insurance agency to be “very satisfying.”

For clients, Flagship offers a “community feeling” with “all the bells and whistles of a big agency,” Jennifer said. The company keeps up with all the changes and complexities in health insurance, and is able to offer services that even some larger agencies can’t.

“We have the most up-to-date management software that’s available for P&C [property and casualty insurance] clients anywhere,” Dave said, explaining that the system compares the previous year’s coverage with the current year, lays out options for additional coverage, and more. “The client is so much more informed than they had been in the past.”

In regards to employee benefits, Flagship has the ability to manage everything internally without outsourcing to a third-party. Jennifer said many employers find Flagship’s all-encompassing services to be a “huge relief,” especially if they operate multiple locations.

As for the future of Flagship, Jennifer said she’s in it for the long haul, and she hopes to continue operating the company until she retires.

Dave also has a long-term mindset, and stated, “My goal is to be alive to see our 100th.”

News and Information. Advertising and Marketing.

Advertise in over
250+ MN newspapers