P&C Core Insurance Transformation Engagement Director

Key Responsibilities & Expectations

• Lead Enterprise Transformation - Drive large-scale P&C insurance core system modernization initiatives across personal and small commercial lines, ensuring successful design and execution aligned with strategic objectives.
• Create and Maintain Program Charters, Roadmaps, Budgets, and Release Strategies - Ensure deliverables meet quality standards and business goals.
• Implement Governance Structures - Establish governance structures (Steering Committee, Architecture Review Board, Change Advisory Board, Testing Council) and enforce RACI, RAID, OKRs, and quality gates across all phases.
• Apply Structured Estimation & Financial Control - Apply an end-to-end estimation process integrated with financial planning, maintain transparency through Earned Value Management, and continuously calibrate forecasts.
• Direct Full SDLC Lifecycle - Oversee all phases from inception through design, build, testing, deployment, hypercare, and optimization, ensuring predictable delivery and operational readiness.
• Ensure Regulatory & Compliance Adherence - Embed controls for NAIC, state DOI, GLBA, HIPAA, PCI-DSS, and other regulatory requirements; maintain auditability and strong data governance.
• Drive Technology Delivery - Lead implementation of core platforms (Guidewire, Duck Creek, Majesco) and ecosystem integrations for billing, claims, document management, payments, and analytics.
• Collaborate & Communicate - Establish clear communication channels with internal teams and stakeholders, manage expectations, and ensure alignment across business and technology.
• Engage with Clients - Engage with clients to understand needs and challenges, provide tailored solutions, and leverage industry expertise to advise on best practices and innovative approaches.
• Monitor & Optimize Performance - Track KPIs, validate benefits against business case, and use metrics and analytics to inform decisions and drive continuous improvement.
• Build & Lead High-Performing Teams - Recruit, develop, and motivate distributed teams across onshore, nearshore, and offshore locations; foster collaboration and psychological safety.
• Demonstrate Strategic & Adaptive Leadership - Balance agile speed with governance rigor, thrive in ambiguity, resolve conflicts pragmatically, and maintain resilience under pressure.

Experience & Qualifications

• 15+ years leading large-scale insurance transformations.
• 10+ years in program leadership for core platform implementations.
• Proven delivery across multi-state regulatory contexts and multi-vendor ecosystems.
• Hands-on experience with Guidewire / Duck Creek / Majesco, scaled agile (SAFe), DevSecOps, and data migration at scale.
• Track record in financial stewardship (EVM, ETC/FTC, cost-of-delay) and estimation frameworks listed above.
• Bachelor's in Business/Technology (Master's preferred).
• Preferred Certifications - PMP or PgMP, SAFe SPC/RTE, CSM/PSM, ITIL, AWS/Azure/Google (Architect/Cloud), Lean Six Sigma (for process).