Insurance Campaign Institute Prepares Agents to Step Up for Public Office

• By: Will Jones
• April 24, 2026

Insurance agents are stepping beyond the agency and into the political arena—and the Insurance Campaign Institute is helping them get there.

During the Friday morning breakfast session at the 2026 Big “I” Legislative Conference, Nathan Riedel, Big “I” senior vice president, federal government affairs, hosted a fireside chat with two Institute attendees from the April 20–21 program in Washington, D.C.

One of them, Jennifer Winkler, owns The Peeples Insurance Agency in Sarasota, Florida, and is a Republican candidate for the House District 74 seat.

Winkler said her decision to run came out of “a perfect storm”—not the hurricanes that hit Florida’s coast in prior years, but a moment when she realized the progress on reform could easily be undone.

“In the summer of 2025, I was at the FAIA Summer Leadership Conference in a legislative meeting with about 100 insurance nerds like me. We were celebrating real reform,” she recalled.

However, after learning that a dozen bills had been filed that could undo all of this and that there was one insurance agent in the Florida House of Representatives, she decided that “we cannot go backward” and “needed to step up and take one for the team.”

The other panelist, Kentucky State Representative Michael “Sarge” Pollock, was elected to represent the 51st District in 2021 and is an insurance agent with Jessie Insurance Agency in Campbellsville, Kentucky.

Similarly, Pollock “decided to stop complaining from the bleachers and get in the game,” he said. “It’s a big commitment, but it’s incredibly rewarding.”

“When I was first elected, there were only three insurance agents in the Kentucky General Assembly, and I was the only one deeply involved in property & casualty,” he said. “I became the insurance voice. Not to run every bill, but to inform what those bills should look like.”

But, as a business owner, the decision to run for office was not something Winkler took lightly. “The scariest thing was putting myself out there politically as a conservative Republican business owner,” she said. “My dad said, ‘You built this business. Why risk it?’ I worried I’d lose clients who don’t agree with me politically.”

“But insurance affordability is one of the top issues in Florida, and my clients see that,” she said. “I’ve had clients who don’t usually vote Republican vote for me.”

The Insurance Campaign Institute was designed to equip insurance professionals with the tools and knowledge to run and win campaigns for public office. Pollock noted that “the presenters were spot-on,” he said. “Every one of them had real, hands-on experience.”

“In 2021, I went through a campaign without anything like this,” Pollock said. “If I’d had this training, it would’ve made everything easier.”

The agenda covered getting your house in order, such as family, agency and values, before you ever put your name out there. They talked about fundraising, messaging, public speaking, door-knocking, and what happens when you actually win.

With so much at stake, Winkler said that “second place isn’t an option,” but thanks to the Insurance Campaign Institute, “it’s already made me stronger … I’m excited to make a difference.”

Both panelists emphasized that the skills agents rely on every day translate naturally to the campaign trail—and ultimately, to effective public service.

“Insurance agents already have the skills: trust, adaptability, problem-solving, and listening. We’re made for this— we solve problems,” said Pollock.

“Insurance agents make the best, perfect candidate,” agreed Winkler.

The inaugural Insurance Campaign Institute was sponsored by five Ambassador sponsors—the American Property Casualty Insurance Association (APCIA), CNA, The Hartford, the National Association of Mutual Insurance Companies and Travelers—and five Partner sponsors—Progressive, RLI, Selective, Westfield and Liberty Mutual.

“Today was something special,” said Melissa Weaver, head of government affairs at Westfield. “Those candidates got some incredible access to the leading experts.”

“This will be a wildly successful program,” she added.

Will Jones is IA editor-in-chief.