Systems Administrator, Azure DevOps (ADO)

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 Systems Administrator, Azure DevOps (ADO), you will be responsible for establishing, governing, and evolving the use of Azure DevOps as a core platform supporting delivery across value streams. This role ensures that ADO Boards, backlogs, workflows, and reporting structures are configured to enable visibility, consistency, and effective flow of value.

Partnering closely with Scrum Masters, Agile Coaches, Engineering Managers, and IT Portfolio Managers, the ADO System Administrator balances governance with flexibility—ensuring teams can operate effectively while maintaining enterprise standards. This role also supports automation, user management, and data access through pipelines, Active Directory integration, and ADO APIs.

What you’ll do

ADO Governance & Operating Model

• Establish and maintain a governance model for ADO Boards and backlogs across value streams.
• Define and enforce standards for:
  • Work item types and hierarchies (Epic, Feature, Story, Bug)
  • Area Paths and Iteration Paths
  • Workflow states and transitions
  • Field usage and data integrity
• Ensure consistency in how teams’ structure and manage work while allowing for context-specific flexibility.
• Partner with Portfolio Operations and delivery leadership to evolve ADO practices in alignment with delivery maturity.

Backlog & Board Configuration

• Configure and maintain ADO Boards to support value stream delivery, including:
  • Backlog structures and levels
  • Swim lanes, filters, and board views
  • Custom fields and rules
• Support teams in aligning their boards to flow-based delivery practices and readiness standards.
• Troubleshoot and resolve configuration issues impacting team execution or visibility.

User Access & Automation

• Manage user access and permissions in alignment with organizational policies.
• Execute and maintain pipelines and automation for user provisioning via Active Directory.
• Ensure appropriate role-based access controls are in place across projects and teams.
• Support onboarding of new users and teams into ADO.

Reporting, Analytics & API Utilization

• Leverage Azure DevOps APIs and analytics capabilities to:
  • Develop and maintain reporting solutions
  • Enable visibility into delivery metrics (e.g., flow, throughput, backlog health)
  • Support Portfolio and Program-level reporting needs
• Partner with stakeholders to translate reporting requirements into scalable solutions.
• Ensure data quality and consistency to support reliable insights.

Intake, Support & Continuous Improvement

• Serve as the primary intake point for ADO-related requests from:
  • Scrum Masters
  • Agile Coaches
  • Engineering Managers
  • IT Portfolio Managers
  • ADO Business Users
• Triage, prioritize, and fulfill requests related to configuration, reporting, and access.
• Provide guidance and education to teams on effective use of ADO.
• Identify opportunities to improve tooling, automation, and governance practices.

Reporting & Role Context

• Supports: Value Streams, Delivery Teams, and Portfolio Leadership
• Partners closely with:
  • Scrum Masters & Agile Coaches (ways of working)
  • Engineering Managers (team structure & access)
  • IT Portfolio Managers (visibility & reporting)
• Primary platform: Azure DevOps (Boards, Pipelines, Analytics, APIs)

How This Role Fits in the Ecosystem

• IT Portfolio Managers orchestrate the work that is prioritized and how value flows.
• Scrum Masters enable how teams execute and improve delivery.
• ADO System Administrator enables the system of record and visibility, ensuring tooling supports both execution and decision-making.
• Together, these roles ensure alignment between delivery practices, tooling, and portfolio insights.

This Might Describe You

• Strong experience administering Azure DevOps (Boards, Pipelines, Security, Analytics)
• Experience defining and implementing governance models for work management tools
• Familiarity with Active Directory integration and user provisioning automation
• Experience working with REST APIs for reporting or automation
• Strong understanding of Agile delivery practices and work item management
• Systems thinker who balances standardization with team flexibility
• Clear communicator who can translate technical configurations into practical guidance
• Comfortable supporting multiple teams in a dynamic, evolving environment
• Experience in enterprise or regulated environments preferred

Preferred Skills

• Experience with Azure DevOps Analytics or Power BI integration
• Scripting experience (e.g., PowerShell, Python) for automation
• Familiarity with CI/CD pipelines in Azure DevOps
• Experience supporting large-scale Agile or value stream-based delivery models

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 recruiting@hagerty.com 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

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If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!