Come join the tech company that's revolutionizing the commercial insurance industry, and having fun along the way. Welcome to our waddle.
our cultureour PERKS

Some of us come out of insurance, others don't but we all have one goal: cut the friction out of commercial insurance. We're seeking fellow team members who think differently, take calculated risks, and are comfortable being accountable for their decisions.  If you are looking for an environment where a little bit of chaos is a good thing, success is measured in terms of successful conversions versus number of meetings attended, please keep reading.

OUr Current Openings

Perks & Benefits

Casual work environment and attire
• Company outings and events
• Professional development is supported and encouraged
• Choose your equipment and software
• Snacks, coffee, and happy hours
• Lunch provided one day a week
• Flexible schedule
• No micromanagement
• Six days paid vacation
• Month-long sabbatical at five-year anniversary
• 50% of health insurance premiums covered
• And Many More


We value a fun and dynamic atmosphere that is low-key, open, and forward-thinking. We have some nice perks, too.

”Bold Penguin is a place where teamwork is highly valued and leaders are empowered. Our culture encourages that on a daily basis.”

- Angie Buccilli
Director, Talent Acquisition

Having Fun Together

We like each other. So we put on a lot of events. A Lot. Baseball games, football tailgates, family bowling nights, company parties, happy hours. None of it mandatory—all of it fun.

Grow Professionally

Certifications, licensing, training, memberships, and conferences. Professional growth is actively encouraged—and often covered.

Giving Back

Columbus has been good to us, so we’re active contributors locally. We also give back to the tech community, through Open Source, articles, and conferences.

Forward Looking

The speed of things here is something! High-energy, highly-collaborative, jump-in-with-both-feet kind of workspace.


We support you. You are our biggest asset.

Onsite Fuel

We know the way to someone's heart is through their stomach, so we always have a variety of sweet and healthy snacks stocked. And, of course, they're free. We also provide a catered lunch on Mondays and proudly brew local coffee like Crimson, Brioso, or Stauf's..

Attire and Attendance

When you're in the office dress up or dress down, it's your call. Whatever makes you comfortable (wearing our Penguins socks is not necessary but can be cool).  When you need a break, take it. Time off is paramount to creating brain space that makes you better when you are in the office. Run errands, watch movies, climb mountains, or hang out at the beach — just share your stories with us when you get back. We are closed for six holidays, too.

Stay Healthy

We're scrappy and get a ton of work done. But we don't believe in compromising your health for the sake of productivity. If you're sick, stay home. Need to go to the doctor? Go for it. After 90 days of employment, we pay a portion of health insurance. Our benefits package includes medical, dental, vision, 401k match, reimbursements, short and long term disability, and life insurance.

Parental Leave

Bold Penguin is proud to support growing families. A paid parental leave is available to birth and adoptive parents and spouses during the first 12 weeks following the birth or adoption of a child. We will help plan for your time away, so that you can focus on your new family.