Director Software Development Jobs in Mansfield, 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

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.

Required Qualifications

• 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.

Preferred Qualifications

• 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.

Education
Bachelor's Degree

Pay Range

The typical pay range for this role is:

$175,100.00 - $334,750.00

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.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

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.

This fulltime position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial wellbeing of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

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

We anticipate the application window for this opening will close on: 08/20/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.