Help Us Bring Small Business Insurance Online

Do Work that Matters

Without insurance small businesses would struggle to exist. Helping small businesses get insurance faster is what we are about. By building the infrastructure that makes small business insurance work better, Bold Penguin is empowering millions of small businesses to do their best work while reducing inherent risks.

The old way of doing small business insurance forced agents to fill out paper applications, underwriters to wade through emails, and small businesses to wait months for coverage. Our founders, an agent turned technologist (Ilya), a geneticist turned engineer (Ben), and a worn out insurance agent (Marc) decided to do something about it.

Be Bold

Dive into new opportunities and make an impact.
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Be You

We embrace the quirks. So show up and be yourself.
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Be Remote

Work from here, there, or anywhere. We've leaned into the remote work lifestyle and embraced it.
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Be Evolving

Be curious, learn more, and we’ll help you get there.
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Be Balanced

We take pride in having a work-life balance and encourage time off and vacations.
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Be Bold

The story goes that our CEO Ilya was watching a nature show and he saw a penguin enthusiastically plunge off an iceberg into the ocean. That’s a bold penguin, he thought. Voila, the company was named.

Are you the type of person that would jump into the ocean? When you come across a new opportunity, do you dive in? If so, Bold Penguin is for you. Heck, if you don’t see a job that fits you, let us know what does. We always want to talk to people that are bold and interested in fixing commercial insurance.

Be You

Bold Penguin folks come with their quirks. At Bold Penguin we embrace those quirks and we want you to share your weirdness with the world.

For a taste of Bold Penguin quirkiness, look no further than our marketing department and the infamous “I’m not a penguin” video. You may recall the famous meme of a Zoom legal proceeding involving an ill-timed cat filter. The Bold Penguin marketing department mobilized and quickly convinced Jim Struntz (COO), Marc DeLeonibus (co-founder), and David Embry (Bold Penguin customer) to film a “I’m not a penguin” spoof. Did the video win an Emmy? No (not yet). Did it scratch our weird itch? Yep.

So please, show up and be you.

Join us and help build digital infrastructure.
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Be Remote

Most positions can be located anywhere (think: at home with your pet, a lakeside patio, or a mountain retreat), with some positions requiring working out of a specific location, including our Columbus, OH headquarters.

Despite a dispersed workforce, we still find ways to collaborate (like at Penguin Talk, our hack-a-thon) and to celebrate together (like a football tailgate party). And, if you ask nicely, you can join us at a baseball game, a hockey game or maybe even Vegas!
It’s flexibility like this while maintaining a laser focus on our people that named us a Best Place to Work in Insurance by Best Insurance in 2022.

And though we're in many locations, we still find ways to celebrate together. In early 2020, when we launched a new insurance carrier, we jumped on a Tik Tok trend to share the good news. In 2022, we took an RV around the country to see our remote colleagues.

Be Evolving

Small business insurance is changing rapidly and we want to join with people that can do the work, see into the future and adapt quickly. The work you have planned may change. Long-held beliefs could be upended by new technology. We want to work with people that can evolve with emerging trends and technologies.

Our company supports curious people through formal and informal learning opportunities. We host virtual luncheons to learn about new parts of the business. We recently launched online learning opportunities. And many times, the best learning opportunities happen informally, as you work with your colleagues.

Be Balanced

Everybody has their own favorite ways to recharge and refresh and we're all about that. No matter what you do in your down-time—play pickleball or make pickles; run with the dogs or nap with the cats; crave the nightlife or sofa-surf, we want your off-hours time to be yours.

If giving back to the community is your thing, Penguins are proud to stand tall with you. Which is why Bold Penguin people proudly pedal with Pelotonia to end cancer, take the Polar Plunge in support of Special Olympics Ohio, and play meaningful roles in numerous other events that feed our passions outside the office.

We also send out adorable onesies! 

Bold Perks & Benefits

Choose-your-own gear

Office equipment is your call. Whether you prefer Mac or PC, laptop or tablet, we’ll set you up for success.

Full health coverage

Our plan covers 50% of your medical premiums. We also offer dental, vision, life insurance, and disability.

Savings plan

Take full advantage of our 401k match right from the start.

Parental leave

A strong flock stands with its families. We offer parental leave for all of our families.

Casual dress code

Whatever your style, dress up or dress down, it’s your call.

Penguin bling

Like swag themed after a certain antarctic bird? Just. You. Wait.