Senior Director, Insurance Transformation (Project Management)

About the role

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.

Requirements

• 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 implementations (Duck Creek).
• Vendor management experience.
• Proven expertise in:
  • Dependency mapping across parallel workstreams
  • Work sequencing under real constraints
  • Critical path and critical chain planning
  • Capacity and bottleneck management
  • Rolling schedule and delivery forecasting
• Strong executive communication skills, including the ability to challenge optimistic assumptions constructively.
• Advanced proficiency with project planning and tracking tools (e.g., ADO, Smartsheet, Lucid, similar).

Qualifications

• PMP Certification (Project Management Professional).
• Experience working within a matrixed organization or enterprise PMO/TMO environment.
• Background in systems modernization, insurance platform implementations, or large-scale operational transformation initiatives.
• Familiarity with Agile, hybrid, or iterative delivery models in large transformations.
• Background in insurance operations (underwriting, policy admin, billing, claims, distribution) strongly preferred.

Schedule

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.