Meet Mark Hara

Learn about our Chief Operations Officer and President of Insurance


When your company’s mission is to lead one of the oldest and largest industries into the tech revolution, you need a team (or maybe even a waddle) with diverse skills and experiences. Enter Mark Hara, our Chief Operations Officer and President of Insurance. Having experienced commercial insurance from every angle, Mark offers a unique perspective, which he shares with our team in this interview.

Professional Philosophy: Be happy with what you’re doing. Align what gives you a sense of purpose with how you make a living, and always intend to do the right thing.

What is your role as Chief Operations Officer?

I work with our internal team and our network of partners to develop sustainable processes that allow Bold Penguin to grow, scale, and deliver a great customer experience. I also work closely with our Customer Success Advocates as they help small business owners find the right insurance as quickly as possible.

What is your role as President of Insurance?

In addition to my involvement with day-to-day operations, I work with our insurance carrier partners as they transition onto our platform. In basic terms, I help them gain exposure for their products and achieve their goals.

What events led to you joining the Bold Penguin team?

That’s an interesting story. Earlier in my career, I worked for Nationwide Insurance, which is an excellent company with a lot of exceptional products and people. That’s where I developed an appreciation for serving small business owners from an insurance carrier perspective. Next, I shifted to Mylo/Lockton to lead an insurance broker. The mission was much the same, but we were selling insurance directly to the small business owner.

I learned about Bold Penguin at the InsureTech Connect conference in 2017. I really appreciated what they were trying to accomplish and quickly signed Mylo up. So, my first experience with Bold Penguin was as their customer. I loved the partnership so much that I ended up going to work for them and to this day, Mylo is still a Bold Penguin partner.

So, I’ve seen commercial insurance from the carrier side, agency side, and as a Bold Penguin customer. It’s a unique perspective that has a significant influence on how I do my job.

What is the boldest thing you've ever done?

I co-founded Cristo Rey, a college preparatory high school. These types of schools create opportunities for underserved student populations to help them better prepare for and graduate college. At the time, Columbus didn’t have anything like it, so a friend and I established Cristo Rey. The kids get a college preparatory high school education, but they also work at a company one day a week to gain real-life experience to better prepare them for a career.  

What is the most challenging aspect of your job?

Any time you're doing something new, the exciting part is also the challenging part. Testing new things, figuring out what works, encouraging people to reframe how they're looking at a problem — all of these activities can be difficult, but they’re also incredibly rewarding.

What do you think makes a technology company successful?

I think success is having smart people with diverse backgrounds who understand how to use technology to solve old problems in new and different ways.

What is your favorite thing about working at Bold Penguin?

The customers. We serve people that are willing to take a risk and put everything they have into a business to help other people. They are the backbone of our economy and I love that we get to be the people who support small businesses as they make an impact on communities all over the United States.

Do you have any non-work related skills or talents that colleagues or acquaintances might not know about?

I play the drums. I’ve been playing since I was in the third grade and to this day, I'm always tapping on something.

Recent Articles

The fifth installment in the Bold Penguin series on The Evolving Risks Of Small Businesses addresses the excess and surplus needs and available high-risk insurance coverage for small commercial customers.

Top 100 Corporate Counsel Award recognizes leadership excellence and commitment

Bold Penguin is a great place to work and is now certified as a Most Loved Workplace® backed by the research and analysis of the Best Practice Institute (BPI)

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