P&C Core Insurance Transformation Engagement Director

P&C Core Insurance Transformation Engagement Director

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 will manage large-scale programs, ensuring alignment with the company's strategic objectives and operational efficiencies. The Engagement Director will also strengthen 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 SDLCfrom 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.

A successful candidate will bring deep insurance domain expertise across both personal and small commercial lines. They will understand the full breadth of personal lines products, including Auto (BI, PD, UM / UIM, PIP, MedPay), Homeowners, Renters, Condo, Landlord, Umbrella, Boat / Marine, Valuable Personal Property, Flood (NFIP), and Earthquake coverage. They will also have hands-on knowledge of the claims value chain, from First Notice of Loss (FNOL) through coverage verification, investigation, evaluation, negotiation, settlement, salvage and subrogation, fraud detection, litigation, and recovery. In addition, they will be well-versed in policy and billing processes, including rating, underwriting, endorsements, renewals, cancellations, reinstatements, payment methods, dunning, and refunds.

On the commercial side, the candidate will understand Business Owners Policy (BOP), Commercial Auto, Workers' Compensation, General Liability, Commercial Property, Inland Marine, Cyber, and Professional Liability. They should be familiar with commercial-specific workflows, such as multi-location risks, schedules, certificates, audits, loss control, and producer / agency integration.

Beyond technical and domain knowledge, the candidate will demonstrate exceptional behavioral competencies. They will think strategically and systemically, seeing interdependencies across business, technology, risk, and operations. They will exhibit executive presence and influence, simplifying complexity and driving decisions at the C-suite level. They will be outcome-oriented, anchoring delivery on measurable value and using data-driven insights to guide progress. Adaptability is keybalancing agile speed with governance rigor and thriving in ambiguity. They will navigate conflicts pragmatically, maintain resilience under pressure, and communicate with clarity and confidence. As a talent builder, they will foster high-performing, distributed teams and create an environment of psychological safety. Integrity and compliance will be non-negotiable, ensuring controls and auditability throughout.

Finally, the candidate will have extensive experience leading large-scale insurance transformations, with at least 15 years in the industry and 10 years in program leadership for core platform implementations. They will have delivered programs across multi-state regulatory contexts and multi-vendor ecosystems, with hands-on experience in platforms like Guidewire, Duck Creek, or Majesco, and expertise in scaled agile (SAFe), DevSecOps, and data migration. Strong financial stewardship skills, including Earned Value Management and forecasting, are essential. A bachelor's degree in business or technology is required; a master's degree and certifications such as PMP, PgMP, SAFe SPC / RTE, Agile, ITIL, or cloud architecture are highly preferred.