DevOps Engineer, Duck Creek

Hagerty

1d • Remote

About The Position

Hagerty is a company built by drivers for drivers, dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. They are the world’s largest insurer of collectible and enthusiast vehicles and home to the Hagerty Drivers Club. Their business includes Marketplace for live and digital sales, driving events, concours, and award-winning automotive journalism. As a DevOps Engineer, Duck Creek, you will independently execute and enhance build, deployment, and environment operations across the Duck Creek platform. This role involves leading release cycles, troubleshooting complex issues across modules, and improving the performance and reliability of environments and services. This work directly supports the stability and scalability of a platform that powers core insurance capabilities at Hagerty, offering deeper ownership of software delivery and operations, solving complex operational problems, and shaping deployment and reliability practices.

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
• 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
• Regularly analyze logs, alerts, and telemetry from tools like Sumo Logic, Pingdom, Dynatrace, or PagerDuty, and use them to guide troubleshooting and identify patterns
• Ability to identify weaknesses in deployment or environment workflows and implement improvements that increase stability, repeatability, or speed
• Ability to mentor junior engineers by helping them understand how pipelines, environments, and observability tools interact and how to think through operational problems
• Communicate effectively across engineering, product, and operations, offering structure and clarity in complex or high-pressure situations
• Balance immediate problem resolution with longer-term improvements, documenting what is learned and sharing insights with others
• Comfortable developing deep expertise in new platforms and technologies.

Responsibilities

• Lead CI/CD pipeline execution and coordinate deployments across multiple environments.
• Validate deployment readiness, identify issues early, and take corrective action.
• Maintain deployment standards, branching structure, and release documentation.
• Collaborate with development, QA, product teams, and Duck Creek support teams throughout release cycles.
• Support environment and product upgrades, including validation and post-deployment checks.
• Manage environment variables, deployment configurations, and workstation alignment across environments.
• Perform complex environment setup, configuration changes, and cross-module troubleshooting.
• Monitor system performance trends and recommend corrective or preventive actions.
• Improve runbooks, SOPs, and environment management practices based on observed gaps.
• Handle ODW provisioning, version upgrades, and inventory lifecycle management.
• Participate in and help lead the on-call rotation, resolving high-impact issues.
• Facilitate troubleshooting sessions and identify root causes across modules and integrations.
• Document remediation steps, timelines, and contribute to post-incident reviews.
• Identify recurring failure patterns and recommend reliability improvements.
• Enhance incident response processes, communication clarity, and operational readiness.

Benefits

• Comprehensive benefits and perks that set us apart (details available upon inquiry for specific jurisdictions)
• US Benefits Overview
• Canada Benefits Overview
• UK Benefits Overview

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees