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 behind—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 brought on a team that’s not only incredibly talented, but also 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.


In your role as a staff engineer you will be tasked with solving our hardest problems by leading and architecting complex, highly-scalable solutions; along with performing as a strong individual contributor on the team.

At this point in your career you will have had a broad-range of technology acumen as well as a depth of experience in more than one area. You will have a significant impact on the engineering organization itself by helping advance Bold Penguin’s software engineering discipline.


  • Engage across product teams to plan, coordinate, architect, and deliver high-complexity features
  • Ensure that solutions are built with security, performance, and fault-tolerance in mind
  • Be an expert in modern cloud architecture and concepts in software engineering such as continuous integration, continuous delivery, DevOps and site-reliability engineering
  • Collaborate with product managers, designers, site-reliability engineers, and customers to build powerful, impactful products
  • Participate in the full lifecycle of the software development life cycle from ideation to delivery
  • Mentor more junior engineers in areas such as unit testing, continuous integration, DRY/SOLID principles, SDLC, etc. to facilitate career growth on the team


  • 10+ years of professional engineering experience (with at least 5 years of it being Ruby on Rails)
  • Previous working experience in high-growth technology companies and/or startups
  • Ability to articulate very complex technical concepts to technical and non-technical people
  • Experience building highly-resilient, cloud-native applications
  • Full-stack expertise in multiple tiers of modern web applications (e.g. front end, back end, infrastructure, etc.)
  • Bonus points for open source contributions and/or speaking experience.
  • Working experience in high-growth technology companies or startups very desirable.


We make quoting and binding faster, simpler, and more profitable for everyone.

Technology we use