We didn’t create Bold Penguin because commercial insurance is broken. It isn’t. But as the world has gotten more connected and digitized, commercial insurance lags — creating a fragmented landscape where businesses, agents, and insurance companies struggle to interact in a smooth and easy way. That’s why we’ve built a highly efficient exchange that cuts the friction out of commercial insurance by connecting everyone to the right quote in record time.

Powering the world of insurance is no small feat, so we’ve built a team that's incredibly talented and passionate about our potential to upgrade the entire industry. As more and more companies, big and small, depend on our technology to operate in the commercial insurance space, we’ll need the best talent all around to support our growth. That’s why we’re looking at you (yes, you!) to make a bold move and join our adventure.


As a Lead Cloud and SRE you’ll be busy doing everything from writing application code and managing infrastructure-as-code to architecting cloud applications for high availability. You’ll be responsible for taking applications to production and providing early support for applications in production.


Design modern containerized or cloud-based applications.  

Build and support Bold Penguin’s automated CI/CD pipeline.

Identify and fix system issues while keeping a cool head.

Spend a good deal of time on software development (the “dev” part of DevOps!)

Lead and mentor the team


Experience using Cloud computing platforms (especially AWS) and applications that scale proficiency in several programming languages (Ruby on Rails, JavaScript).

Experience using configuration management tools such as Ansible, Packer, and Terraform.

Excellent communication skills.

A head for data-driven decision-making.

Bonus Qualifications:

Previous experience working in the insurance industry, especially commercial insurance.

Previous experience working in high-growth tech startup companies.


We offer competitive compensation and progressive benefits that include:

Medical, Dental, and Vision

Disability and Life Benefits401K with a company match

Employee Assistance Program

Parental Leave

Paid Time Off

Remote Culture. Here at Bold Penguin our remote employees are top of mind, and we have created an inclusive, engaging remote environment.

Choose-your-own gear. Whether you prefer Mac, PC, or Linux, one screen or three, we’ll set you up for success.

Stay connected to the Glacier. We slack. A lot. We also like to video conference regularly. We even have all- hands "Waddles" held Tuesday - Friday 12:00PM EST.

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

Bold Penguin believes in inclusion. That’s why we’re proud to be an equal opportunity employer that considers all qualified applicants regardless of race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, beak size, or inability to fly.

To learn more about our results-focused culture and employee-focused perks, read more on our careers page.


Cloud Engineering
Ruby (Programming Language)
Amazon Web Services
Insurance Products