Insurance Transformation Leader — Remote Apex Platform

Hagerty Insurance Agency; United States; Remote; USD 180,000 - 280,000; Full time

Job summary

Hagerty is seeking a Senior Director of Insurance Transformation to lead the Apex platform rollout, owning the integrated schedule across Policy, Billing, Claims, Distribution and Data. You will map dependencies, refine the critical path, and push for data‑driven delivery decisions.

The ideal candidate has hands‑on PM experience with large insurance system implementations (Duck Creek), vendor management, and expertise in Scrum/SAFe.

Qualifications

• Proven experience delivering complex, cross‑functional transformation initiatives in insurance or financial services.
• Demonstrated hands‑on experience with core insurance system implementations (Duck Creek).
• Vendor management experience.
• Dependency mapping across parallel workstreams.
• Capacity and bottleneck management.
• Rolling schedule and delivery forecasting.

Responsibilities

• Own the integrated master schedule for Apex across multiple workstreams (Policy, Billing, Claims, Distribution, Data, Integrations, Forms).
• Build and refine the critical path, protect delivery buffers, and escalate decisions with data-backed recommendations.
• Active management of cross-team dependencies and sequencing to optimize end-to-end outcomes.
• Force trade-offs between scope, timing, and capacity; reforecast milestones based on reality.
• Lead and integrate multiple Project Managers responsible for bounded delivery slices.
• Ensure program-level plans roll up into the integrated schedule; enforce readiness criteria.

Education

PMP Certification

Tools

ADO

Smartsheet

Lucid

Job description

Hagerty is seeking a Senior Director of Insurance Transformation to lead the Apex platform rollout, owning the integrated schedule across Policy, Billing, Claims, Distribution and Data. You will map dependencies, refine the critical path, and push for data‑driven delivery decisions.

The ideal candidate has hands‑on PM experience with large insurance system implementations (Duck Creek), vendor management, and expertise in Scrum/SAFe.