Senior DevOps Engineer (Hybrid/Remote)

Senior DevOps Engineer (Hybrid/Remote)

Cover Whale

$177,000 - $195,000

Who is Cover Whale?

Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program. Our safety program is proven to save lives while delivering better insurance for our drivers.

We provide easy insurance options for our drivers at industry-leading insurance loss ratios for the insurance companies that support Cover Whale. The Commercial Auto and Trucking segment of the insurance industry badly needs our help and so do the hard-working drivers who have been struggling with ever-increasing insurance costs year-after-year. Join us in the mission!

Founded in 2019, Cover Whale recently closed a $15.5M seed funding round (the largest InsurTech seed round raised in North America) and is scaling rapidly. For more information, please visit

Cover Whale is ranked 374th in the Forbes 2023 America’s Best Startup Employer America's Best Startup Employers 2023 (

What We’re Looking For:

Cover Whale is searching for a Senior DevOps Engineer to join our rapidly growing Engineering team. This position will provide an excellent opportunity to impact multiple business areas. You must be comfortable with ramping up and moving quickly, dealing with ambiguity, and delivering in an agile fashion. Now is your chance to be part of a team at the forefront of a new industry. You will bring technical expertise with a passion for enabling the successful adoption of containerization and distributed-compute technologies.

What You’ll Do:

  • Provide technical expertise while implementing solutions for Cover Whale’s rapidly expanding customer base.
  • Lead the implementation of distributed and automation technologies in Cover Whale’s environments, including Docker, IaaS, Git, container orchestrators, and continuous integration platforms.
  • Collaborate with Product Management, internal stakeholders, and external vendors to improve development, deployment, and operations.
  • Foster a continuous learning environment through continuously improving processes, procedures, and approaches.
  • Engage with product development teams as a trusted partner to provide feedback and collaborate on issues.
  • Help to establish and document implementation best practices and socialize them with the Cover Whale team to ensure repeatable success.
  • Create proof-of-concept and pilot demonstrations of technology to customer groups


The Expected base pay for the role will be between $177,000 - $195,000 at the commencement of employment. However, base pay if hired will be determined on an individualized basis and is only part of the total compensation package, which, depending on the position, may also include discretionary bonus and other Cover Whale-sponsored total rewards/benefits.


  • 5+ years of experience as a DevOps Engineer or similar role.
  • Located in the US.
  • Full stack experience in the software life cycle from development to operations.
  • Experience building and delivering software solutions focused on engineering, execution, and operational excellence.
  • Experience effectively working with teams in remote and geographically dispersed locations and understanding the inherent implications and challenges of working as part of a global team.
  • Excellent communication skills and the ability to explain complex technical topics.
  • Expert knowledge of Linux.
  • Experience with IaaS, PaaS, and AWS cloud technologies.
  • Hands-on “Production” experience working with container platforms and supporting technologies such as Docker, Kubernetes, EKS, ECS, GitHub Actions, etc.
  • Experience with Continuous Integration/Continuous Delivery Patterns and their implementation.
  • Experience with domain-driven design and event-driven architectures.
  • Experience working with APIs and knowledge of HTTP and REST principles.



  • Health/Dental/Vision
  • Life/Disability
  • Employee Assistance Program
  • Flexible Vacation Policy
  • 401k – Employer Match
  • Generous Parental Leave

Cover Whale works to maintain the best possible environment for our employees, where individuals can learn and grow with the company. We strive to provide a collaborative environment where each person feels encouraged to contribute to their processes, decisions, planning, and culture.

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law.

product management
Software Development