Director of Insurance Portfolio Management

As the Director of Insurance Portfolio Management, you will be a strategic and operational leader responsible for driving the successful delivery coordination of complex insurance initiatives across multiple teams, systems, operational functions, and programs. Operating within Insurance Operations and serving as a critical integrator to the enterprise plans, this role partners closely with the Insurance Hubs and Spokes, IT PMO, Technology Management Office (TMO) to ensure cohesive planning, prioritization, and execution of the insurance project portfolio at large.

This leader oversees a team of project managers who provide “boots-on-the-ground” execution support and ensures that operational teams, product managers, actuarial, filing, and technology contributors remain aligned to planned timelines, deliverables, and strategic objectives. The Director translates enterprise and insurance strategy into an actionable project portfolio roadmap while orchestrating cross-functional collaboration from intake through delivery across multiple areas.

Ready to get in the driver’s seat? Join us!

What you’ll do

Strategic Leadership & Project Portfolio Management

• Serve as the strategic owner of the insurance project portfolio, ensuring alignment with the Insurance President’s vision and broader organizational strategy.
• Define the intake and upfront prioritization process for new project initiatives, ensuring clarity of scope, resource needs, cross-functional impacts, and expected value.
• Maintain a holistic view of all in-flight and upcoming insurance programs to guide sequencing, capacity planning, and risk mitigation for the upstream & downstream teams involved.
• Partner with Implementation Directors and insurance operational leaders to align roadmaps, milestones, and readiness activities across all insurance business functions.

Cross-Functional Program Execution

• Act as the primary liaison between Insurance Operations and IT PMO/TMO to ensure seamless coordination, shared understanding of requirements needs, and alignment on project delivery timelines.
• Assist the Hub leaders, Spoke leaders and Implementation Directors in removing their stucks/roadblocks within the intake pipeline. Provide meeting facilitation for that group as needed.
• Collaborate with operational teams to track milestone progress, including:
  • Training and readiness tasks
  • User Acceptance Testing (UAT) timelines and deliverables
  • Requirements gathering and SME resource allocations
  • Operational process changes required to support deployment
• Partner with Actuarial, Filing, and Regional Product Management teams to orchestrate regulatory, pricing, filing, and product development timelines that feed upstream and downstream technology and operational workstreams.

Team Leadership & Development

• Lead, mentor, and develop a small team of project managers responsible for day-to-day execution and cross-functional coordination of the strategic execution methodology defined above.
• Provide guidance on project management best practices, risk and issue management, stakeholder communication, and delivery methodologies.
• Foster a culture of ownership, accountability, continuous improvement, and business acumen within the project management team.

Governance, Reporting & Communication

• Establish and maintain project intake governance frameworks, dashboards, and reporting to provide transparency into portfolio and project status, dependencies, risks, and decisions required.
• Establish and maintain the project intake process using modern tooling that assists in tracking and visibility to project lifecycle.
• Ensure delivery teams and leadership have clear visibility into timelines, capacity constraints, and operational readiness.
• Facilitate executive-level communication to ensure alignment, escalate risks, and support decision-making.

This might describe you

• 7+ years of progressive project and program management experience, including leadership responsibilities.
• Deep experience in auto insurance operations, product, or systems transformation programs.
• Demonstrated success managing complex cross-functional initiatives involving both business and technology teams.
• Proven ability to lead project managers and foster effective team dynamics.
• Strong understanding of insurance operational processes such as underwriting, servicing, claims, compliance, product development, and regulatory filing.
• Excellent communication, stakeholder management, and facilitation skills.
• Ability to navigate ambiguity, manage competing priorities, and drive alignment across diverse groups.
• A strategic thinker with strong operational instincts and the ability to see both the “big picture” and the execution details.

Preferred

• PMP Certification (Project Management Professional).
• Experience working within a matrixed organization or enterprise PMO/TMO environment.
• Familiarity with Agile, hybrid delivery models, or product-centric organizations.
• Background in systems modernization, insurance platform implementations, or large-scale operational transformation initiatives.

The ideal candidate is:

• A connector who facilitates collaboration across business, product, actuarial, filing, and technology functions.
• A disciplined project management leader who brings structure, accountability, and clarity.
• Highly organized and skilled at managing complex portfolios with interdependent initiatives.
• Confident engaging with senior leadership while also supporting team members and operational SMEs.

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.

Say hello to Hagerty

Hagerty is an automotive enthusiast brand and the world’s largest membership organization. Along with being a best-in-class provider of specialty insurance for enthusiasts, Hagerty is also home to the Hagerty Drivers Foundation, Hagerty Drivers Club, Marketplace and so much more. Committed to saving driving for future generations, each and every thing Hagerty does is dedicated to the love of the automobile.

Hagerty is a rapidly growing company that values a winning culture. We provide meaningful work for and invest in every single team member.

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.

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. 

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