Diane "Dee" Thibodeau

CEO and co-founder, Charter Solutions
Diane "Dee" Thibodeau

There’s little that Dee Thibodeau enjoys more than bringing people together—for a business goal, a charitable cause, a community initiative or a bit of fun. She’s the ultimate convener of people and companies, using her tireless energy to power Charter Solutions, propel numerous organizations and assist anyone in her large network.

A serial entrepreneur who has launched and grown diverse companies, Thibodeau co-founded Charter Solutions in 1997 and serves as co-CEO. It survived many tech booms and busts by focusing on technology consulting and evolving its services to meet prevailing needs. Thibodeau deftly guided the company as it transitioned into information services with core capabilities in analytics and professional services that include systems architecture, planning and management focused mainly on health care, financial and government clients.

Currently, Charter Solutions enjoys a steady growth clip after it pivoted to analytics, leading clients through a process that builds a culture of fact-based decision making. “I love consulting. You feel good when you have helped a business grow and expand and think differently in a short amount of time,” says Thibodeau. “I love to be involved with the clients—I never want to be sitting at a desk all the time.”

Helping businesses learn more about their operations through analytics reflects Thibodeau’s lifelong love of learning. She knew she wanted to emulate her entrepreneur father. Her track record includes growing Microworx into the largest computer training company in the Midwest, as well as starting management consulting and hotel investment businesses.

More recently, Thibodeau joined veteran women executives and angel investors to launch the Sofia Fund, which invests in women-owned or -led technology and health businesses. It’s familiar territory for Thibodeau, who has dedicated her career to nurturing women leaders and entrepreneurs and helping lead organizations involved with health care and technology.

She also makes it her mission to help others find opportunities to grow and lead, constantly meeting people for coffee or meals, and cold-calling others she wants to meet. “I really enjoy helping people be successful, and I’m very passionate about getting women on boards, because there are not that many women directors,” says Thibodeau, who helped start Women Corporate Directors in Minnesota. “If I can help an individual better their life or move to their next career, that’s exciting. That’s what it’s all about.”

Dr. Sheila Riggs, chair of the department of primary dental care at the University of Minnesota, got one of those calls from Thibodeau when she moved from Iowa to the Twin Cities. After meeting her for networking, Thibodeau encouraged Riggs to join the Women’s Health Leadership Trust, a 36-year-old organization that Thibodeau worked to reinvigorate. She watched as Thibodeau helped grow the organization from 60 members to more than 350.

“Dee is so high-energy and gives the whole room a can-do spirit. She has tenacity, and she stays engaged at this high level for years,” Riggs says. “She wants to make sure this community is as strong as possible, and she’s in it for the long run. Dee is a key ingredient to why the fabric of this community is so tightly woven.”

What was your first experience as a leader?

I first ran a computer training company called Microworx. They hired me as general manager, and when I started, there was nothing there. They didn’t even have a curriculum. So I hired the best instructor in the computer field that I could, and we ended up being the largest Midwest training company in the country. I learned [you should] ask a lot of questions before you get involved with a company. Then jump in and make it happen.

What was your hardest lesson in work or life?

To not do everything myself in my work or family life. Surround yourself with people who have talents you don’t have, and let them run with it. I’m controlling and like to have it done a certain way, but you have to let people use their talent and let them go—and if they make mistakes, it’s a learning situation. Also, surround yourself with people who are not like you. I used to surround myself with people who are like me, because they are fun. But if their expertise, talent and style aren’t different, it’s not good for the organization.

What is your best habit in work or life?

Perseverance. People don’t persevere and they show up and wonder why it doesn’t happen. In business, I think of it as a challenge. Then it’s not depressing or a downer. It’s exciting. If you approach life and business that way, then you grow with challenges. That’s what life is all about. I always want to be learning and growing. Sometimes you need a different approach, and that helps me persevere.