Key Takeaways
- Bold Penguin is a two-time Most Loved Workplace® — recognized in both 2021 and 2026.
- The IT Systems Support Engineer role puts you at the center of a fast-moving, technology-driven insurtech company.
- Bold Penguin offers comprehensive health, wellness, and financial benefits alongside a vibrant, community-first culture.
- The company fosters genuine career growth through cross-functional collaboration, cutting-edge technology, and transparent leadership.
What Is It Like to Work at Bold Penguin?
Bold Penguin is not your average tech company. Founded in 2016, it has grown into a leading insurtech platform that is reshaping how small commercial insurance is quoted and bound. The culture is social, loyal, and community-oriented — just like the penguins the company is named after. Every team member is called a "Penguin," and that is not just a nickname. It reflects a real commitment to boldness, belonging, and doing meaningful work together.
Why Should IT Professionals Consider Bold Penguin?
For IT professionals, Bold Penguin offers something rare: the chance to support critical technology at a company that is genuinely transforming an industry. As an IT Systems Support Engineer, you will work with an API-driven exchange and scalable quoting-engine infrastructure that powers real business outcomes for agents, brokers, and carriers every day. Your work will matter — and everyone will know it.
Bold Penguin has earned the Most Loved Workplace® certification for both 2021 and 2026, a recognition that reflects its deep commitment to employee satisfaction, inclusion, and a positive work environment. This is a company that has proven, year after year, that it puts its people first.
Apply for the IT Systems Support Engineer role at Bold Penguin and join a team that values your skills and your growth.
What Does the IT Systems Support Engineer Role Involve?
In this role, you will be a key player in keeping Bold Penguin's technology running smoothly. You will collaborate across departments, troubleshoot systems, and help the team stay agile and productive. Because Bold Penguin operates at the intersection of technology and insurance, no two days look the same. You will have the opportunity to work with cutting-edge tools and alongside engineers, analysts, and product teams who are all focused on one unified goal.
Does Bold Penguin Support Career Growth?
Absolutely. Bold Penguin is built around the idea that growth happens when people are empowered, informed, and included. Leadership keeps communication transparent through company-wide "waddle" meetings where every department shares what they are working on. There are also Friday coffee chats with the CEO and pitch competitions called "Penguin Tank" — giving every employee a voice and a direct line to leadership. For an IT professional, this kind of visibility accelerates growth fast.
What Benefits Does Bold Penguin Provide?
Bold Penguin takes care of its team with a well-rounded benefits package, including:
- Comprehensive health insurance and mental health support
- Employee Assistance Program (EAP) with nine sessions per category per year
- Flexible Spending Accounts (FSAs) for dependent care
- Competitive compensation and critical illness insurance
- Commuter and transportation reimbursements
- Voluntary benefits package
Beyond the standard perks, Bold Penguin invests in its culture through events like Penguin Palooza — a multi-day in-office celebration — team lunches, and daily Slack collaboration that keeps the community tight even as the company scales.
What Makes Bold Penguin's Culture Unique?
Bold Penguin's culture DNA can be summed up in a few words: social, bold, loyal, agile, and community-oriented. These are not values posted on a wall — they are lived daily. Cross-functional collaboration is the norm, not the exception. Teams are encouraged to experiment, move fast, and solve hard problems together. There are no silos, just shared ownership of outcomes.
This culture of genuine care extends to IT professionals who want to grow their technical skills while being part of a team that celebrates both professional wins and personal milestones. At Bold Penguin, you are seen as a whole person, not just a headcount.
Ready to Take the Leap?
Bold Penguin is growing, and the IT Systems Support Engineer role is your opportunity to be part of something transformative. From its Most Loved Workplace® recognition to its vibrant penguin culture, this is a company where IT careers truly thrive. Apply for the IT Systems Support Engineer position today and see what it means to work somewhere you are truly valued.