Senior Digital Transformation Director Jobs in Springfield, MA

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 ourselvesaccountable 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.

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.

In this high-impact role, you will serve as the senior engineering executive for the transformation, owning the technical strategy, engineering roadmap, and software delivery accountability across the program. You will own the technology vision, strategic roadmap, and delivery accountability for the full transformation program spanning: digital experience, data and AI platforms, service operations, and core platform modernization. You will lead a multi-disciplinary organization directly responsible for digital platform engineering and data & AI, while governing transformation execution across the broader engineering organization and partnering with Product, Architecture, and Delivery functions.

Success in this role will require building strong partnerships across CVS Health and Aetna technology organizations, leveraging enterprise capabilities, and aligning transformation decisions with broader enterprise technology strategies while delivering business-specific outcomes. You will be the technology face of the transformation to executive business sponsors, accountable for translating a bold growth ambition into modern, AI-native, cloud-based capabilities that drive measurable business value.

Key Responsibilities:

• 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 workstreams 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.

Required Qualifications:

• 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 objectives with enterprise technology strategies, governance processes, and architecture standards.
• Strong executive presence, with a track record of partnering with and influencing VP and C-suite business stakeholders on strategy, trade-offs, and investment decisions.
• Experience owning a significant technology budget, vendor portfolio, and resource planning across a large, complex engineering organization.
• Proven experience building and owning technology investment business cases and driving measurable value realization at the program level.
• Demonstrated people leadership building high-performing engineering cultures and developing senior leaders.
• Strong breadth across data engineering and data platform modernization, with the ability to set and evolve an enterprise data strategy that enables AI-native capabilities.

Preferred Qualifications:

• Experience modernizing large scale legacy core platforms into modern cloud and microservices architectures.
• Strong background in healthcare third-party administration, managed care, or health benefits administration technology landscape.
• Demonstrated experience building differentiated, omni-channel customer or member experiences including native mobile applications, modern web portals, and integrated digital communications.
• Experience modernizing service operations, transforming contact center, case management, and customer service technology.
• Hands-on experience embedding generative AI and intelligent automation into production healthcare workflows.
• Experience operating in a highly matrixed enterprise with shared services across Product, Architecture, Delivery, and Infrastructure Organizations.
• Track record of designing multi-year leadership succession and organizational capability plans.

Education:

Bachelor's degree in engineering, computer science, information systems, or a related quantitative discipline, or equivalent work experience.

• Graduate degree preferred.

Pay Range

The typical pay range for this role is:

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company's equity award program.

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Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

Additional details about available benefits are provided during the application process and on Benefits Moments.

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