Winegar Credits Mentors for His Success in Trucking Specialty

He’s only 30, and newly married, but Courtland Winegar may have already amassed enough time in the wholesale industry to be considered a veteran in the space.

Winegar, a transportation specialist at Crouse & Associates Insurance Services in Sacramento, Calif., hasn’t known much else professionally.

When he graduated from the University of Nevada, Reno in 2013 with a bachelor’s of science degree in finance, he had a job lined up as financial planner with Ameriprise in Las Vegas, Nev.

He had a flight booked from his home in California to accept the job, when his brother, Rob Brignone, a producer/broker, convinced him to first take a trip to talk about opportunities with the leaders at Crouse, a large wholesale broker.

Winegar headed to San Francisco and meet Greg Crouse and Pam Quilici, a pair of executive vice presidents at the firm. After speaking with the two, he realized he could make the same amount of money, and still have the work-life flexibility he sought in a career. He was convinced insurance was the business for him.

He started with Crouse’s in-house managing general agent for his first year, focusing on learning what would eventually become his specialty – trucking.

His time underwriting commercial trucking submissions on behalf of a carrier Crouse had the pen for, and shadowing his brother and Greg Crouse, helped him learn the business from the ground up while he built his book of business by splitting accounts with both.

“I kind of built my book and learned that way initially,” Winegar said.

By focusing on trucking, he was following his brother’s footsteps and building a passion for his specialty.

“What I like about trucking is it’s so strategic,” he said. “The stakes are high. One small thing could blow up the entire account. You really just have to go 100% into trucking to be successful.”

While many professionals tend to start out on the retail or carrier side and then move to wholesale, Winegar has no qualms about jumping right into a difficult segment of the insurance business.

“I think what I like about wholesale is the people you’re dealing with,” he said. “I’m dealing with insurance agents and I’m also dealing with underwriters. Those two people couldn’t be more different.”

He explained that underwriters are often technically minded people who tend to be more introverted, whereas agents are “sales people to the max.”

“As a wholesaler, it’s my job to kind of be a chameleon and get along with both sides,” he said. “You find a lot of characters on the wholesale side. They work hard, play hard.”

And he doesn’t regret pursuing insurance as a career.

“The thing I like most about the insurance industry is it’s basically like you’re running your own business,” he said. “Your success is a direct result of your effort and what you do. It’s all up to you.”

However, he does find one thing difficult about being in insurance.

“I think the tough part for me is that you’re not really seeing sort of a physical end-product,” he said. “You’re dealing with numbers and quotes. It’s not like you’re an architect and you’re seeing a finished product at the end of the day.”

Despite that mental hurdle, which he’s found ways around, he believes his career to this point is a success, which he attributes to a philosophy he learned early on from his Crouse mentors, who taught him three keys to success for a wholesale broker: seeing your agents; putting in the time; knowing your product.

“My book’s $25 million right now in premium,” he said, offering a bit of advice to any young newcomers who are listening.

“First of all, I think the most important thing is to surround yourself with people who are also doing well and have them as a mentor.”