Director Insurance Jobs in Chicago, IL (NOW HIRING)

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 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.

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 key—balancing 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.

Requirements

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.
• Develop Strategic Plans – Create and maintain program charters, roadmaps, budgets, and release strategies, ensuring deliverables meet quality standards and business goals.
• Establish Robust Governance – Implement governance structures (Steering Committee, Architecture Review Board, Change Advisory Board, Testing Council) and enforce RACI, RAID, OKRs, and quality gates across all phases.
• Implement 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.
• Foster Client Relationships – 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.
• Generative AI - have a strong understanding of the use of Gen-AI across the SDLC.

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.
• Bachelors 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).

Benefits

This position comes with competitive compensation and benefits package:

1. Competitive salary and performance-based bonuses
2. Comprehensive benefits package
3. Home Office model
4. Career development and training opportunities
5. Flexible work arrangements (remote and/or office-based)
6. Dynamic and inclusive work culture within a globally known group
7. Private Health Insurance
8. Retirement Benefits
9. Paid Time Off
10. Training & Development
11. *Note: Benefits differ based on employee level

About Capgemini

Capgemini is a global leader in partnering with companies to transform and manage their business by harnessing the power of technology. The Group is guided everyday by its purpose of unleashing human energy through technology for an inclusive and sustainable future. It is a responsible and diverse organization of over 340,000 team members in more than 50 countries. With its strong 55-year heritage and deep industry expertise, Capgemini is trusted by its clients to address the entire breadth of their business needs, from strategy and design to operations, fueled by the fast evolving and innovative world of cloud, data, AI, connectivity, software, digital engineering and platforms. The Group €22.5 billion in revenues in 2024.