Janessa Weiland, 39

Janessa Weiland took a leap of faith in 2009 when she left her job as sales director of a Naples boutique hotel to join brother-in-law Brian Chapman’s startup — 75 miles north in Port Charlotte.

“I knew nothing about insurance,” says Weiland, who studied hospitality management in college.

Photo by Mark Wemple

It’s a gamble Weiland is glad she took.

Today, she’s COO and managing partner of Chapman Insurance Group, a growing full-service insurance brokerage based in Fort Myers with five offices along Florida’s coast.

She is a “hands-on, roll-up-your-sleeves trailblazer,” writes Jaden Cuenca, a Chapman employee, who nominated Weiland for 40 under 40 recognition.

Weiland, who manages the independent agency’s six-person executive team, says Chapman Insurance Group is successful because of its nearly 100 employees, which includes the first ones hired.

“I’m a big proponent of elevating others, teaching others to do better than I can do,” she says. “The minutes you spend helping someone today often saves you hours tomorrow.”

Weiland says Florida’s ever-changing insurance market is ideal for independent agencies. As more insurers move into the state, more options are available to consumers. “We represent so many carriers to provide the best solutions to our clients,” Weiland says.

The agency plans to continue its organic growth and expand its online presence as more consumers shop for insurance through the internet. “Opportunities will present themselves,” adds Weiland. 

As for Weiland’s leadership skills, she gives much credit to the example set by her mother, Janet Stedcke, a former missionary and nurse. “I have witnessed how respected and loved she is by both those she has led and those that have led her,” Weiland says.

Weiland, in her 40 under 40 survey, says her mom is wise, selfless and listens with the intention to understand. 

Lessons she’s learned from her include: focusing on what you can control, holding yourself to a higher standard than you hold others to, and realizing your legacy will be greatly impacted by how well you learn to love people along the way.