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.

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. Your health and growth as a professional are the foundation of our company.

Snacks on Snacks

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, so you can get your week started right.

Drink Local

We're proud to support local brewers and roasters. Our mornings are fueled by local roasters such as Crimson Cup, Brioso, or Stauf’s, and happy hours often feature the latest craft brew.

Dress for Your Success

Dress up or dress down, it's your call. We will institute casual Fridays, or make you pay to wear jeans. Whatever makes you comfortable (within reason, of course), works for us.

Choose Your Axe

MacBook Pro, Microsoft Surface, or that latest Dell XPS Ultrabook (along with your favorite software). Prefer a keyboard with mechanical keys? Or maybe just a magic trackpad? We want you to do your best work, and to do the best work you need the best tools.

Time Off Is Important

We have better things to do than waste a bunch of time micromanaging your time out of the office. Time off is paramount to creating brain space that makes you better when you are in the office. Climb mountains, go sky diving, 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 50% of health insurance premiums for you and your family.

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.