Executive Director, Underwriting Business Technology - Caremark

Executive Director, Underwriting Business Technology

We're building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you'll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.

The Executive Director, Underwriting Business Technology will lead the strategy, development, and evolution of the technology platforms that support underwriting, pricing, and financial offer operations. This leader serves as the primary bridge between Underwriting, CFAO, and Digital, Data, Analytics & Technology (DDAT), translating business requirements into technology solutions that enable accurate, scalable, and efficient client pricing.

The underwriting technology ecosystem supports sophisticated pricing models, configurable business rules, actuarial assumptions, and workflow processes that generate client-specific pricing proposals. This role is responsible for defining the technology roadmap, prioritizing investments, and overseeing the development and support of the systems and tools that power these capabilities.

Success in this role requires a leader who can effectively align business and technology teams, drive complex development initiatives, influence stakeholders across a matrixed environment, and ensure underwriting platforms continue to evolve in support of changing business, client, and regulatory needs.

Technology Strategy & Product Ownership

• Define and execute the technology strategy and roadmap supporting underwriting and pricing operations.
• Translate business needs into technology priorities, ensuring platforms remain aligned with evolving market, client, and regulatory requirements.
• Identify opportunities to improve scalability, flexibility, automation, and user experience across underwriting tools and processes.
• Evaluate emerging technologies and best practices that enhance underwriting capabilities and operational efficiency.

Platform Development & Delivery

• Lead the development and enhancement of underwriting systems and tools used to configure pricing assumptions and generate client pricing proposals.
• Partner closely with DDAT to drive solution design, platform modernization, and execution of development priorities.
• Ensure platforms effectively support complex algorithms, business rules, analytical models, and workflow requirements.
• Oversee production support and continuous improvement efforts to ensure platform performance, stability, and usability.

Program & Portfolio Leadership

• Lead a portfolio of strategic underwriting technology initiatives, establishing governance, roadmaps, success metrics, and delivery plans.
• Manage prioritization, budgeting, resource planning, and stakeholder alignment across initiatives.
• Drive disciplined program execution while managing dependencies, risks, and competing priorities.
• Ensure technology investments deliver measurable business value and support strategic objectives.

Enterprise Partnership & Business Enablement

• Serve as the primary liaison between underwriting, finance, actuarial, analytics, and DDAT teams.
• Build alignment across stakeholders to ensure technology investments support business objectives and strategic priorities.
• Partner with business and technology leaders to enhance pricing capabilities, underwriting workflows, and overall operational effectiveness.
• Strengthen integration between underwriting platforms and the broader Caremark technology ecosystem.

• 12+ years of experience in technology development, business technology, product management, software platforms, or related fields.
• Demonstrated ability to translate business priorities into scalable technology solutions.
• Experience leading complex technology initiatives across business and technology organizations.
• Strong understanding of technology development life cycles and experience partnering with engineering and technology teams.
• Proven ability to influence…