Remote Insurance Transformation Director & Delivery Leader

Hagerty; United States; On-site; USD 180,000 - 240,000; Full time

Job summary

Hagerty in the United States is seeking a Senior Director of Insurance Transformation to lead the Apex platform delivery across policy, billing, claims, and data domains. You will own the integrated schedule, align cross‑functional teams, and drive data‑backed decisions to ensure on‑time, high‑quality delivery.

You bring hands‑on experience with large insurance implementations (Duck Creek, Guidewire), strong vendor management, and a proven ability to forecast milestones.

Qualifications

• Proven experience delivering complex, cross-functional transformation initiatives.
• Hands-on delivery of large-scale insurance system implementations (Duck Creek).
• Vendor management experience and multi-method delivery (Scrum, SAFe, etc.).
• Strong executive communication and governance skills.
• Experience with dependency mapping across parallel workstreams.

Responsibilities

• Own the integrated master schedule for Apex across policy, billing, claims, distribution, data, integrations, and forms.
• Lead cross-team dependencies and optimize end-to-end delivery.
• Re-forecast milestones based on real execution data and risks.
• Partner with IT APMO to align plans with capacity and vendor capabilities.
• Serve as the single point of synthesis across business and IT delivery efforts.

Skills

Transformation leadership

Cross-functional delivery

Stakeholder management

Risk management

Dependency mapping

Critical path planning

Capacity planning

Delivery forecasting

Executive communication

Education

PMP Certification

Tools

Azure DevOps (ADO)

Smartsheet

Lucidchart

Job description

Hagerty in the United States is seeking a Senior Director of Insurance Transformation to lead the Apex platform delivery across policy, billing, claims, and data domains. You will own the integrated schedule, align cross‑functional teams, and drive data‑backed decisions to ensure on‑time, high‑quality delivery.

You bring hands‑on experience with large insurance implementations (Duck Creek, Guidewire), strong vendor management, and a proven ability to forecast milestones.