OSCPA member leads as CFO for $1 billion valued startup

By Jessica Salerno, OSCPA senior content manager

A car insurance app that decides how much to charge people by how well they drive is shaking up the insurance industry. For OSCPA member Cindy Powell, CPA, CFO of Root Insurance Co., that’s all part of the plan.

“We want to be the best auto insurance company in the world,” she said.

Powell stated it simply: if you’re a bad driver, you should pay more. If you’re a good driver, you should pay less. Drivers download the company’s app onto their cell phone, it measures their driving behavior and that data is used as the primary source in determining their price. There is no need to open the app when driving because it runs in the background.

Root was recently named growth-stage company of the year at the VentureOhio Awards. And a recent $100 million in a Series D funding round pushed its valuation to $1 billion.

Powell has a deep insurance background, spending 26 years at State Auto Insurance Companies. That’s where she met Root’s CEO, Alex Timm, when he interned as a college student. They stayed in contact over the years, and Powell joined the board in 2016, coming on full time as CFO in 2017.

Powell credits much of her ability to grow at State Auto to taking on new and different opportunities with the help of mentors. She held various roles in the company, including chief accounting officer and chief audit executive.

“I always worked really hard and suddenly I realized it was 20 years later,” she said with a laugh. “I just find the industry very interesting and saw first-hand that it’s ripe for change. I got to see State Auto grow in very interesting ways, which is helping in my current role.”

She describes her CFO responsibilities as “broad,” overseeing accounting, finance, capital management, investments, claim operations and legal. But she said she prefers it that way, noting one of the core capabilities of accountants is building relationships, and educating and influencing others.

Her background as a CPA only enhances those capabilities, and as she continues to build her team at Root, she has the credential in mind.

“My goal here is to build an accounting function that is CPA credentialed,” Powell said, “because you have to have a certain mindset and commitment to earn the CPA

She said one of the benefits of being at a start-up is the freedom to make quick decisions and begin executing on them. Their fast-paced way of thinking also extends to their attitude toward failure.

“Learn from failure, and then let’s move on,” she said. “In larger companies people sometimes dwell on it.”

Root operates in 20 states around the U.S., and the company’s goal is to be nationwide by the end of 2019. With all of buzz Root is receiving, it could be easy for company leaders to let the hype go to their heads. But Powell said while accolades are nice, she is focused on Root’s making a difference in the insurance industry.

“I actually ignore what’s out there because it’s just noise to me,” she said. “It’s good noise, don’t get me wrong. You can get wrapped up in that excitement, but we have so much to do and so much to change.”