Executive Director, Software Engineering AI Solutions

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, Software Engineering – AI Solutions will lead the design, development, and delivery of AI-powered software products and platforms that drive the Health100 strategy. Reporting to the VP of Engineering, this leader will be responsible for building and scaling a high-performing software engineering organization focused on leveraging Generative AI and agentic technologies to solve complex healthcare and business challenges. This role serves as the senior engineering leader responsible for translating business opportunities into production-grade software solutions. The Executive Director will define technical strategy, lead multiple engineering teams, establish engineering excellence practices, and partner closely with Product, Security, and Business stakeholders to deliver innovative AI-enabled applications at enterprise scale. The ideal candidate combines deep software engineering leadership experience with a strong understanding of modern AI technologies and a proven ability to build and scale engineering organizations that deliver measurable business outcomes.

Key Responsibilities

• Lead software engineering teams responsible for the design, development, deployment, and support of AI-powered applications and platforms.
• Establish engineering best practices, software development standards, architecture governance, and operational excellence.
• Drive the delivery of secure, scalable, resilient, and maintainable software solutions.
• Foster an engineering culture centered on innovation, accountability, quality, and continuous improvement.
• Lead development of AI-enabled products that improve customer experiences, operational efficiency, clinical workflows, and business performance.
• Establish reusable frameworks, services, and accelerators that enable rapid delivery of AI use cases across Health100.
• Evaluate emerging technologies and identify opportunities to create competitive advantages through AI.
• Drive modernization of existing services and applications through AI-assisted capabilities and automation.
• Recruit, mentor, and develop engineering leaders and technical talent.
• Partner with Product Management to define technical solutions that align with business priorities.
• Collaborate with product, design, Security,  Engineering, and Infrastructure teams to ensure successful delivery.
• Communicate engineering strategy, roadmap, risks, and outcomes to executive leadership.
• Drive measurable business value through technology investments.

• 15+ years of software development and technology leadership experience.
• 10+ years leading large-scale engineering organizations.
• 5+ years delivering AI, ML, or Generative AI solutions within enterprise software environments.
• Experience building cloud-native platforms and distributed systems at scale.
• Deep expertise in software architecture, modern engineering practices, APIs, microservices, DevSecOps, and cloud technologies.
• Proven track record of leading organizations with 50+ engineers across multiple teams.
• Experience delivering large-scale customer-facing and enterprise software solutions.
• Strong executive communication and stakeholder management skills.

• Experience building AI-native products from concept through production deployment.
• Healthcare, pharmacy, payer, provider, or digital health experience.
• Experience with LLMs, agentic architectures, conversational AI, and intelligent workflow automation.
• Experience building internal platforms that enable enterprise-wide AI adoption.
• Strong understanding of Responsible AI, model governance, and AI security.

The typical pay range for this role is: