DevOps Engineer, Duck Creek

Say hello to Hagerty Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We’re proud to be the world’s largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world’s largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We’re committed to Never Stop Driving. Ready to get in the driver’s seat? Join us! As a DevOps Engineer, Duck Creek, you will independently execute and enhance build, deployment, and environment operations across the Duck Creek platform. You will lead release cycles, troubleshoot complex issues across modules, and help improve the performance and reliability of our environments and services. This work directly supports the stability and scalability of a platform that powers core insurance capabilities at Hagerty. In this role, you’ll gain deeper ownership of how software is delivered and operated, solve complex operational problems across systems and integrations, and help shape how our deployment and reliability practices evolve. What you’ll do

• Ensure stable, predictable delivery of Duck Creek releases and deployments by:
• Leading CI/CD pipeline execution and coordinating deployments across multiple environments.
• Validating deployment readiness, identifying issues early, and taking corrective action.
• Maintaining deployment standards, branching structure, and release documentation.
• Collaborating with development, QA, product teams, and Duck Creek support teams throughout release cycles.
• Supporting environment and product upgrades, including validation and post-deployment checks.
• Maintain a healthy, observable, and production-ready Duck Creek environment ecosystem by:
• Managing environment variables, deployment configurations, and workstation alignment across environments.
• Performing complex environment setup, configuration changes, and cross-module troubleshooting.
• Monitoring system performance trends and recommending corrective or preventive actions.
• Improving runbooks, SOPs, and environment management practices based on observed gaps.
• Handling ODW provisioning, version upgrades, and inventory lifecycle management.
• Improve the reliability and operational performance of Duck Creek services by:
• Participating in and helping lead the on-call rotation, resolving high-impact issues.
• Facilitating troubleshooting sessions and identifying root causes across modules and integrations.
• Documenting remediation steps, timelines, and contributing to post-incident reviews.
• Identifying recurring failure patterns and recommending reliability improvements.
• Enhancing incident response processes, communication clarity, and operational readiness.

This might describe you

• 5+ years of experience in DevOps, platform engineering, or software delivery
• Experience working with CI/CD tools such as Azure DevOps, Jenkins, or Octopus
• Strong experience with monitoring and observability tools (e.g., Sumo Logic, Dynatrace, Pingdom, PagerDuty, or similar)
• Ability to troubleshoot issues across multiple systems, environments, and pipeline stages
• Experience supporting or operating enterprise applications across multiple environments
• Experience with Duck Creek
• You are comfortable investigating issues across CI/CD tools such as Azure DevOps, Jenkins, or Octopus, and can reason about how a failure in one stage affects others
• You regularly analyze logs, alerts, and telemetry from tools like Sumo Logic, Pingdom, Dynatrace, or PagerDuty, and use them to guide troubleshooting and identify patterns
• You can identify weaknesses in deployment or environment workflows and implement improvements that increase stability, repeatability, or speed
• You mentor junior engineers by helping them understand how pipelines, environments, and observability tools interact and how to think through operational problems
• You communicate effectively across engineering, product, and operations, offering structure and clarity in complex or high-pressure situations
• You balance immediate problem resolution with longer-term improvements, documenting what you learn and sharing insights with others
• You are comfortable developing deep expertise in new platforms and technologies.

Other things to note

• This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week.
• May require travel for quarterly events.
• Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email [email protected] for compensation, comprehensive benefits and the perks that set us apart. At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference. We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world. #LI-Remote / #LI-Hybrid / #LI-Onsite EEO/AA US Benefits Overview Canada Benefits Overview UK Benefits Overview If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!