Senior Director, Insurance Transformation (Project Management)

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!

The Senior Director of Insurance Transformation is the senior execution leader responsible for driving predictable delivery of Hagerty’s Apex insurance platform transformation. This role is designed for a hands-on project management professional with deep experience delivering large-scale core insurance system implementations (e.g., Duck Creek, Guidewire, Majesco).

What you’ll do

Program Execution & Delivery Leadership

• Own the integrated master schedule for Apex across multiple parallel workstreams (Policy, Billing, Claims, Distribution, Data, Integrations, Forms).
• Build, maintain, and continuously refine the critical path and critical chain, identifying true constraints and protecting delivery buffers.
• Actively manage cross-team dependencies, sequencing work to optimize end-to-end outcomes rather than local efficiency.
• Force explicit trade-offs between scope, timing, and capacity, escalating decisions early with data-backed recommendations.
• Re-forecast milestones and delivery dates based on actual execution reality, not static plans.

Project Management & Integration

• Lead and integrate the work of multiple Project Managers responsible for bounded delivery slices (e.g., state readiness, capability releases).
• Ensure project-level plans roll up coherently into the integrated program schedule.
• Eliminate “late discovery” by enforcing readiness criteria before work begins (requirements, environments, data, dependencies).
• Act as the single point of synthesis across business and IT delivery efforts.

Capacity, Risk & Constraint Management

• Partner with IT APMO to align delivery plans with real engineering and vendor capacity.
• Identify bottlenecks and systemic constraints early; re-sequence work proactively.
• Actively manage delivery risk, buffer consumption, and emerging execution threats.
• Ensure risks are surfaced as program-level decisions, not absorbed silently at the team level.

This might describe you

• Proven experience delivering complex, cross-functional transformation initiatives, preferably in insurance or financial services.
• Experience in multiple project/program delivery methods, Scrum, SAFe, etc.
• Demonstrated hands-on experience with core insurance system...