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Senior Director, Insurance Transformation (Project Management)

United States🌐 Remote💼 Full-time🗓 2026-09-01 → 2026-09-25

Core

Senior execution leader driving predictable delivery of Hagerty's Apex insurance platform transformation, managing cross-functional workstreams for policy, billing, claims, and distribution.

Role type

Senior Director, Insurance Transformation (Project Management)

Builds

Apex insurance platform (core insurance systems)

Domain

Insurance / Financial Services

Deliverable

production ML models | product features | dashboards & analysis | research | client delivery | infrastructure | physical/clinical work

Required skills

Large-scale core insurance system implementations, Program execution & delivery leadership, Cross-team dependency management, Critical path and critical chain planning, Capacity and bottleneck management, Rolling schedule and delivery forecasting, Vendor management, Project planning and tracking tools proficiency

Preferred skills

Insurance operations background (underwriting, policy admin, billing, claims, distribution), Systems modernization experience, Matrixed organization experience, Agile/hybrid delivery models

Technologies

Duck Creek, Guidewire, Majesco, ADO, Smartsheet, Lucid

Responsibilities

Own integrated master schedule across multiple parallel workstreams, Lead and integrate work of multiple Project Managers, Enforce readiness criteria to eliminate late discovery, Partner with IT APMO to align delivery plans with capacity, Identify bottlenecks and re-sequence work proactively, Manage delivery risk and buffer consumption

Seniority

Senior Director, hands-on IC

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