DevOps Engineer, Duck Creek

Hagerty is a company built by drivers for drivers, dedicated to making it easier for enthusiasts to drive and celebrate their vehicles. As a DevOps Engineer, you will enhance build, deployment, and environment operations across the Duck Creek platform, ensuring stability and scalability while improving operational performance.

Responsibilities:

• 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

Requirements:

• 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