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 the Director of Cloud Engineering, you will oversee all aspects of our software delivery pipeline, security, reliability, and automation. You will oversee a growing team of cloud & site reliability engineers, information security personnel, and be accountable for the availability of our platform. You’ll use metrics and telemetry to detect problems before they happen. You will take developer productivity very seriously and be constantly finding new ways to improve the flow of value to our customers. 


Ensure that our technology platform meets growing demands and maintains a 99.99% availability 24/7.

Run blameless postmortems; identify root cause of incidents and prioritize remediation.

Evaluate new tools and technologies that help Bold Penguin move faster and/or be more secure.

Maintain and champion our security architecture and controls. 

Stay current with best practices and evaluate new threat vectors and technology.

Experience managing a team is required; will be responsible for a remote team of cloud engineers.

Be a cloud-native leader. 

Create and maintain a roadmap to drive the organization towards continuous delivery and continuous improvement.


Experience with Amazon Web Services; specifically EC2, ECS, ELB, CodePipeline, RDS, S3, IAM, and Lambda.

Deep, hands-on expertise with AWS CloudFormation and other Infrastructure as Code tools.

Ability to articulate Cloud & DevOps concepts to a variety of technical & non-technical team members.

The ability to give clear and actionable direction and performance feedback.

The ability to work here in our home office in Columbus, Ohio.

Bonus points for expertise in implementing security & compliance frameworks such as SOC/2, NIST 800-53, and NIST 800-171 especially on Amazon Web Services.

Experience working in highly-agile and fast-paced environments.

Experience working at technology companies and startups is desirable.


We offer competitive compensation and progressive benefits that include:

Medical, Dental and Vision

Disability and Life Benefits

401K 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.


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