P&C Core Insurance Transformation Engagement Director

P&C Core Insurance Transformation Engagement Director

Be among the first 25 applicants. The P&C Core Insurance Transformation Engagement Director is responsible for leading transformation initiatives for property and casualty insurance. This role demands a visionary leader who can innovate and drive change while collaborating effectively with stakeholders across various functions. The Director manages large-scale programs, ensuring alignment with the company's strategic objectives and operational efficiencies. The Engagement Director also strengthens relationships with key clients, providing expert guidance and insights into industry trends and best practices.

The Engagement Lead / Program Director is the accountable executive for a large-scale insurance transformation spanning multiple jurisdictions and lines of business
. This leader directs program governance
, financial stewardship
, and value realization while orchestrating the full SDLC—from Strategy and Inception through Design, Build, Testing, Deployment, Hypercare
, and Continuous Improvement
. Success requires a mix of deep insurance domain knowledge
, estimation mastery
, scaled‑agile delivery
, and executive stakeholder influence across business and technology.

The Engagement Lead is responsible for implementing a structured, end‑to‑end estimation and governance process that ensures predictability, transparency, and control across the entire program lifecycle. This begins with defining clear scope boundaries, delivery assumptions, and productivity baselines, followed by decomposing work into manageable components and applying consistent sizing standards. Estimates are validated through collaborative reviews and integrated into financial planning, translating effort into cost projections with contingency buffers.

Continuous calibration occurs at key milestones to reflect actual performance, ensuring forecasts remain accurate and risks are proactively managed. All estimation outputs feed into program dashboards and Earned Value Management for full traceability.

In parallel, the role establishes robust program governance through Steering Committees, Architecture and Change Advisory Boards, and Testing Councils, supported by a PMO for planning, reporting, risk management, and vendor coordination. Governance enforces RACI, RAID, OKRs, and quality gates across phases, while maintaining strict controls for scope, change management, configuration, and go‑live readiness. Auditability is ensured through end‑to‑end traceability from requirements to business outcomes.

The Engagement Lead oversees the full SDLC, including initiation and visioning, requirements and design validation, build and integration, testing and quality assurance, release and cutover, hypercare stabilization, and legacy decommissioning. Compliance with multi‑jurisdictional regulations (NAIC, DOI, GLBA, HIPAA, PCI‑DSS) and strong data governance practices are embedded throughout. Finally, the role drives delivery across core platforms (Guidewire, Duck Creek, Majesco) and their ecosystem integrations, ensuring alignment with enterprise architecture and operational readiness.

This structured approach enables predictable delivery, financial transparency, regulatory compliance, and measurable business value
, positioning the program for success from inception through optimization.

Deep insurance domain expertise across both personal and small commercial lines. Experience with full breadth of personal lines products, claims value chain, policy and billing processes, and commercial workflows. Exceptional behavioral competencies: strategic thinking, executive presence, outcome orientation, adaptability, conflict resolution, and talent building. Extensive experience leading large‑scale insurance transformations: at least 15 years in the industry and 10 years in program leadership for core platform implementations, hands‑on experience with Guidewire, Duck Creek, or Majesco, scaled agile (SAFe), Dev Sec Ops , and data migration.

Strong financial stewardship skills, including Earned Value Management and forecasting, are essential. Bachelor’s degree in business or technology…