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Six tips from a successful businessman: Ty Wooldridge

Executive Ty Wooldridge shares what 36 years in the insurance industry has taught him.

Story by Eddy Hoyle

Ty Wooldridge is the president of Aetna Health and Life Insurance and president of Continental Life Insurance, both now part of CVSHealth. Wooldridge has 36 years of experience in the insurance industry but has never resigned or left a job. Due to mergers and acquisitions, he has maintained continuous employment with many familiar names: First Colony Life, General Electric, Genworth Financial, Continental Life and Aetna. Wooldridge leads the Aetna Medicare Supplement and Ancillary product businesses from Nashville, Tennessee.

Under his leadership, total membership grew from under 140,000 to over 1.3 million policyholders, placing Aetna among the top three carriers in the industry. His successful work history includes actuarial science, independent distribution sales leadership, corporate finance, personnel development, profit and loss management, product development and management, government relations, and mergers and acquisitions. He holds a BS degree in mathematics from Liberty Baptist College and the actuarial designations MAAA and FSA.

Originally from Texas, Wooldridge and his wife, Kelly, live in Nashville and have two grown daughters, Beth and Kim. His family has always loved South Carolina and owned a beach house in Myrtle Beach. Years ago a friend told him about Daufuskie Island, and while on a business trip, he decided to check it out. He fell in love, purchased land, joined Haig Point Golf Club in 2017, and his new house will be completed early next year. He is an avid golfer, and he and Kelly enjoy traveling. Here are his tips for success.

Keys to Success

1. Think like an owner. Wooldridge said it’s very important to think like an entrepreneur. “Nobody knows your job like you do,” he said. “Disruptive thinking leads to change. When you think like an owner, you think about how to do things better, more efficiently, and how to make the business a success, or even fill in a gap. Great ideas come from everyone.”

2. Leaders encourage. “When you’re entrusted to lead others, encourage them to think like entrepreneurs,” he explained. “If you can get others to think in that way, they share in the success and responsibility, and they should be recognized, even if, for example, their ideas lead to eliminating their own job. A good leader knows he needs people with ideas and that there will always be a place for them.”

3. Flexibility. “Be very flexible,” Wooldridge said. “The world can change overnight – just as it has with COVID. New work models evolve, and you must be willing to change, to reinvent yourself. We all want security and stability, but to be really successful, that’s the very thing you can’t rely on. Lead the change; don’t passively sit back.”

4. Diversity matters. Wooldridge said we are all really good at three or four different things. So find people whose talents are different from yours. A lack of diversity is weakness.

5. Lead from the front. “People follow a leader because they want to,” he said. When a leader has a clear vision and others are aligned with the vision, they believe their work is important, and that makes all the difference between having a 9-to-5 job or having a job that they feel makes a positive impact. If they have caught the vision, they will accept that the leader is fallible and can make mistakes, but they will never accept doubt about the vision.

6. Enjoy the ride. “Recognize that your life and work is a marathon, not a sprint,” Wooldridge said. “Figure out how to live and enjoy your life so that down the road you don’t regret time not spent with enjoyment.” LL