Bold Penguin's new CFO dives into sea of potential

Rebecca Walters
Dan Gifford, CFO, Bold Penguin

As the “guy filling out multiple applications to obtain business insurance,” Dan Gifford says he knows first-hand the challenges that Bold Penguin solves every day for consumers.

As the insurtech's new CFO, Gifford says he did his due diligence and was completely sold on the company, which offers a platform supporting the commercial insurance industry.

“Once I did more research on what they were up to, I had the chance to meet the leadership team and talked to others in the insurance industry to get their take—all of which were very positive, I was sold,” Gifford says. “I wanted to be a part of what was happening on The Glacier (an internal company nickname for itself).

“Today the number of small and mid-sized commercial business that actually follow through on shopping their insurance is in the mid-20 percent range, primarily because it's so difficult to change insurers, and nobody wants to fill out multiple applications,” Gifford says. “This number could easily double or more in the next five to 10 years, and we're poised to help make this a booming and efficient process for all parties involved."

Columbus CEO conducted a digital interview with Gifford about a variety of topics. Here’s what he had to say.

What’s the toughest job interview question you’ve ever had, and did you nail it? 

I had an interview that started with: “I don’t think we need a CFO, but convince me that I do.” And that wasn’t a setup, it was legitimately how this owner felt. Among many other things, I was able to demonstrate my understanding of the dynamics the company was facing, including uncertainty over potentially losing their largest client and needing to make drastic cuts, what I could take off of their plate, and how important it was for them to have a CFO with my experience to achieve their desired plans. Yes, I nailed it.

What’s one thing people at work would be surprised to know about you?

I started out as a hospitality management major at Florida State and ended up as an accounting major at Otterbein.

Has it been your experience that having a college degree helped you in your career?

Absolutely. The foundational learning has been key to my growth, and there was so much of the college experience that has helped me with my personal and professional development. Without my college experience, I would not have had the friendships and opportunities I’ve been afforded.

If you weren’t in a leadership position with your current company, what else would you like to do? 

As I mentioned above, I thought I wanted to go into hospitality management, but I learned quickly that I was better suited for the patron side of the bar. 

Describe a point in your career where you felt stifled, bored, angry or frustrated, and what did you do about it?

I’ve always been told that when something isn’t going your way, you can be a victim or do something about whatever situation you are in. I had helped a company through two transactions and each time, I was pushed further away from the senior leadership team as a result of merging with a larger company. I was very professional about it and went about my business with the same level of quality I always had, while also pursuing a new role, which I ultimately found.  It was important to me to have a voice at the table and not to squander my skills even if it meant moving on, but it was just as important to me not to burn a bridge in the process of making a career change.

Who or what inspires you in life and why? 

I have a number of people I look up to — most importantly, my father. I learned the importance of having a good work ethic and also making sure you had time for your family from him. He rarely missed a sporting event I was involved in, even if that meant driving two hours from a meeting to make it. At his retirement, one of his colleagues made sure they told me that one of the things they respected most about him was that no matter what the situation was, you could talk to him and how he handled it was fair — he didn’t play favorites or politics. He was a good listener and used sound judgment when making a decision. I think we could all aspire to be thought of in this high regard and to apply these principles when you think about all of the issues we face in our everyday lives.

What was your first job, and how old were you?

I delivered the Columbus Dispatch when I was in my early teens, and I also mowed grass for neighbors growing up. I hated that Sunday paper on a cold or rainy day. It was always nice when my dad let me load up my papers in the station wagon (yes, it was sweet—with faux wood panels and everything) instead of riding my bike on those days.

Rebecca Walters is a freelance writer for Columbus CEO.

Dan Gifford

Age: 54

Position: CFO Bold Penguin           

Held since: July 2020

Hometown: Westerville       

How long lived in Columbus: Most of my life. I spent three years in East Lansing, Michigan, with KPMG, where I met my wife.

Education: Otterbein University, Bachelor’s degree in accounting

Family/Pets: Wife, Dee; children Spencer, 21; Mitchell, 19, both at Otterbein; dog, soft-coated Wheaten terrier, Sparty (in honor of Dee’s alma mater)