Kent Fortune

Born in Biloxi, Miss., to a military family, Kent Fortune doesn’t serve on the front lines, but he provides military members assistance in a different way. As vice president and general manager of USAA Financial Services in Colorado Springs, he helps active and retired military find banking, mortgage and insurance services that suit their specific needs. USAA’s services are offered only to service members and their families. Fortune, 51, spent time with the Business Journal to talk about how he’s worked his way from an entry-level position as an insurance representative at USAA to managing all Colorado Springs operations. Fortune manages 1,600 employees in Colorado Springs, overseeing one of the largest employers in the city.

How does USAA stand out from others in the industry?

I’m very passionate about what we do, so I could talk for days about what USAA does. Our members are at the center of everything we do. In Colorado Springs, nearly 40 percent of our employees are former military and military spouses, which helps us build strong relationships with our members. Our employees’ familiarity with our members drives the office culture and helps us reach the goals we set as a company. This year, the Denver Post named us the No. 1 top large workplace in Colorado and top in workplace dynamics. We’ve gone from 25 original members in 1922 to more than 11 million members now. We’re really that one-stop shop. We’ve been at war for so many years, and our members don’t have much time. We value their time, so they can just call us, and we can put it all together and help them out. Our goal is, by the time they get to retirement, they have all the money that they need through investments, retirement accounts and savings plans.

What is trending in the insurance industry?

Technology’s making everything faster and more convenient. Our members are always on the go, and we’re continuing to develop mobile apps to keep pace with their busy lifestyles. We’re also testing drones to help us handle claims quickly after a disaster. It’s an exciting time to be in this business.

Were there any major challenges?

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Learning this industry from the ground up provides perspective and a strong understanding of how to help lead those around you. You learn so much starting at the bottom. It gives you “street cred,” because when you give advice, you can say, “I know because I did it.” Starting at the bottom and overcoming all those challenges to navigate your way up the ladder … there’s some pitfalls along the way, skinning the knees. How do you pick yourself up?

How did you deal with the pitfalls?

When you’re willing to be vulnerable and take risks, your employees are more likely to do the same. Once I learned it’s OK to try something big and make small mistakes along the way, I was able to adapt my leadership style. You have to be vulnerable — when you make a mistake, you say, “My bad. Let me learn from that and then let me grow.” When employees see their leaders are willing to take a risk and when they make a mistake, it’s OK, they’re going to stretch themselves.

What are the biggest challenges to the industry in Colorado Springs?

I still worry about wildfire. Even though Waldo Canyon was in 2012, and we had the Black Forest fire in 2013, as a city we’re not really infilling, we’re expanding. We’re expanding out into areas that we’ve never been before. [In time], the farther away you get from an incident, you tend to forget about it. For Waldo, I had a front-row seat. I was out in the community. I asked and I asked, “How are we doing? What can we do better? Are there any things we need to improve on?”

“Learning this industry from the ground up provides perspective and a strong understanding of how to help lead those around you.”

What are the solutions to those?

Be proactive. Even though it’s been two years since our last wildfire, the potential exists and drives us to continue to keep a watchful eye as the Colorado Springs community expands. We strongly encourage our members and others in the community to take preventive steps to mitigate their risk using tools provided by their insurance company. Whether you are a USAA member or have another insurer, work with your insurance company so you’ll have the proper defenses against anything that comes along.

Would USAA, do you believe, ever open for non-military?

We already offer investments, life and health insurance to the general public, but certain products will likely always be focused on the military to uphold our dedication to current and former service members and their families.

Talk about your family and what you enjoy doing in your spare time.

My fiancée Stephannie Finley (wedding planned for June 4) and I share a passion for giving back and making a difference in the community. We love Colorado Springs and have family in town and close by in Denver, so we enjoy time with them and watching my nephews play hockey. I enjoy anything I can do with Stephannie, from planning our wedding to volunteering and spending time with the family.


  1. Stephanie is my Brother’s daughter & I am so happy she has found the love.of her life! God is GOOD!!

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