Executive Director, Digital Transformation & Platform Engineering

Position Summary

Are you a technology transformation leader who wants to own the modernization of a multi-billion-dollar healthcare business? CVS Health is seeking an Executive Director, Digital Transformation & Platform Engineering, to serve as the senior technology executive for the modernization of Meritain Health, one of the nation's largest third-party administrators. This is a rare opportunity to architect and lead a multi-year strategic transformation that will redefine how millions of members, employers, brokers, and providers experience their health benefits.

• Serve as the single accountable technology executive for the Meritain transformation program, owning strategic roadmap, financial oversight, and driving key technology decisions across all delivery work streams in alignment with broader CVS Enterprise & Aetna technology strategies.
• Own the development and value realization of the transformation business case, at both the overall program level and the initiative level, ensuring investments deliver measurable, accountable business outcomes and ROI.
• Define and drive the end‑to‑end transformation technology strategy, modernizing legacy core platforms into a modern, AI‑native, cloud‑based ecosystem that enables growth and competitive differentiation.
• Lead the digital platform engineering and data & AI engineering organizations end‑to‑end as direct ownership responsibilities, setting engineering strategy, technical roadmap, and execution priorities for both functions, while owning resourcing, talent development, and skill allocation across teams to deliver differentiated digital experiences and AI‑driven capabilities.
• Govern transformation execution across core platform engineering teams that do not directly report to you, holding them accountable to program milestones, architecture standards, and funding decisions.
• Chair the Transformation Office governance, coordinating Engineering, Product, Architecture, Delivery, and Business in an integrated operating model.
• Own architecture, build‑versus‑buy, and vendor selection decisions across the program, aligning transformation goals with enterprise standards and existing CVS Health and Aetna capabilities while ensuring delivery accountability.
• Drive AI‑native modernization, embedding generative AI, automation, and advanced analytics across the member experience, service operations, and core adjudication and claims processing.
• Partner with and influence executive business sponsors, presenting program strategy, progress, and investment decisions at the executive steering committee level.
• Build the engineering organization’s capability through hiring, technical skill development, and succession planning, developing the next generation of platform and engineering leaders and ensuring durable organizational depth.
• Own software delivery excellence and engineering standards across all engineering teams, including code quality, CI/CD, QA, reliability, and SRE practices, while protecting the stability of existing production systems throughout the transformation.

• 12+ years in healthcare technology or enterprise software, including 5+ years in senior engineering or transformation leadership roles.
• Hands‑on engineering leadership background: has personally led large‑scale software and platform engineering organizations through delivery, not solely strategy or program management.
• Demonstrated accountability for a large‑scale ($80M+) technology transformation or legacy modernization program in a TPA, payer, health plan, or comparable regulated environment owning delivery outcomes, not solely advising.
• Deep technology depth across modern cloud‑native architectures, data platforms, AI/ML, and digital experience engineering, with the credibility to make architecture and build‑versus‑buy decisions.
• Proven ability to lead and influence cross‑functional engineering teams without direct authority, holding peers accountable to shared program outcomes.
• Demonstrated success leading large‑scale transformation programs within highly matrixed enterprises, partnering with shared‑service organizations and balancing business‑specific…