Brett Winingham took his first job in the health care field when he was 17 years old, promoting his stepfather’s general agency for Colorado employee benefits. “This was during the summer breaks from high school,” he said. “My stepdad would send my stepbrother and me out to deliver health insurance benefit materials to brokers all over the state. I would drive to various little towns and check into a hotel using my stepdad’s credit card. I would look up all of the broker locations listed in the local phone book and spend the next one, two, or three days visiting each one – telling them to call my stepdad for more information.”

Today, Winingham leads the sales and account management teams charged with maintaining and expanding Cigna Healthcare's employer-sponsored health plan business throughout Colorado, New Mexico, Utah, and Wyoming.

“I wish I could say I got here by design, but I did not,” Winingham said, explaining that he found success by working as hard as he could while always trying to help others. “Then doors would continually open up,” he said.

Born with a competitive spirit

Winingham strove to do his best from an early age. “I've always been hypercompetitive,” he said. “I love team sports and the dynamic of high individual performance within a team setting – being part of a group and wanting to do your best within that group. It created this hunger within me to always improve.”

His initial goal was to be a professional baseball player. While playing for his high school team, Winingham had a pitching session for a scout from the Minnesota Twins. He blew out his elbow during that session, which ultimately kept him from a career in baseball.

But Winingham never lost his competitive spirit, largely because of two important women in his life.

“My mom was an amazing role model of strength, grit, hard work, and courage. She showed me what an individual could accomplish, regardless of their circumstances,” Winingham said. “And my wife always believed that I was capable of more than I believed in myself. Both of them continue to push me to do better while always being supportive.”

Laying down the law

Winingham graduated from the University of Colorado Denver with a bachelor’s degree in political science, yet he gravitated toward a career in health care benefits.

“I originally thought I wanted to be an attorney,” Winingham said. “I love to write, I love to read, I love to argue, so I thought that was the career for me. Then I looked at the cost of law school and the median salary for a starting attorney at that time and discovered that I actually made more money working for my stepdad in health insurance. So I decided to go back to that.”

However, Winingham did not want his first job after college to be in his stepfather’s agency. “I didn’t want to be ‘the boss’ kid’ of the company, I wanted to go out and grow my career elsewhere,” he said. He asked his stepfather for ideas of where to start looking for work and learned of an opportunity with a national health insurance company, then began selling Medicare Advantage plans in Colorado. Winingham then spent a few years selling large group employer benefit contracts for other national health insurance companies – until his stepfather called upon him.

“His agency had been losing contracts because the insurers decided to leave the Colorado market, but he had an opportunity to rebuild his business thanks to a new contract with a large insurer,” Winingham said. “This rebuilding required someone with experience in landing large employer contracts, so he asked me to help.”

Barely one week after rejoining the agency, a family matter called his stepfather away. His stepfather entrusted Winingham to lead the rebuilding of the business. Within four years, the agency became so successful that it was acquired by a major competitor, which retained Winingham to oversee their sales and operations in Colorado. Eventually, his role expanded to the company’s entire Western region. “I was running seven offices along the coast of California, plus one in Phoenix, Arizona, and one in Denver,” he said. “I essentially spent a decade in a plane, traveling pretty much every week of the year.”

Moving to a culture of yes

In 2017, a business reorganization at his company made Winingham open to new job opportunities. He found one at Cigna Healthcare.

“I represented all of the national health care carriers in Colorado, which were great organizations, but I only saw Cigna Healthcare as a good fit for me,” Winingham said. “Cigna has a culture of high achievement and a strong focus on their customers. It was a ‘culture of yes,’ always looking for ways to address the customer’s particular needs.”

In his current role, Winingham leads local initiatives focused on supporting the community, improving affordability, and driving the personalization of health care services.

“Health care programs need to become a lot more individualized,” Winingham said, noting that employment tends to be much more transient than it was in the past. “My grandad worked for one construction company his whole life. The world isn't that way anymore. I believe the average millennial will have 12 or 13 jobs, or more, throughout their career.” Winingham is proud of how his teams continue to work on ways to tailor health care services to better meet the unique needs of the workforce, today and in the future.

To lead is to serve

Throughout his career, Winingham’s successes have come from his focus on others. “Leadership is all about serving,” he said. “Whether it's a sales effort or a conversation with a co-worker, a direct report, or a superior, it is always about what you can do to help the other person.”

His dedication to serving others includes bringing out the best in his team members and preparing them to become leaders. “I’m glad to be able to help open doors and show people that they're capable of great things,” he said. “It’s great to watch them go forward and take off.”