Lead Director – Software Development Engineering; AI & Automation

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.

The Lead Director – AI Software Engineering is a pivotal role within a dynamic organization, partnering with both business and IT leaders. The position provides the opportunity to make a significant impact for customers utilizing Pharmacy Benefits and involves managing engineering teams focused on testing, automation, and production operations.

• Lead testing and automation strategies across IT and Business Operations using AI platforms, ensuring high-quality, scalable delivery aligned with business objectives and customer experience goals.
• Own end‑to‑end execution of quality assurance processes across AI model validation, automation, and manual testing to drive consistent quality outcomes and timely release cycles.
• Oversee the development and adoption of AI‑Driven Operations (AIOps) and automation capabilities for proactive issue detection, alert noise reduction, and predictive failure prevention.
• Implement AI‑assisted incident triage, automated runbooks, root‑cause analysis, and self‑healing systems.
• Collaborate with the AI Platform team to integrate Large Language Models (LLMs) and Machine Learning (ML) models into operational workflows, including log summarization, anomaly detection, and remediation.
• Champion modern testing and operational practices, including agile testing methodologies, automation frameworks, and AI‑specific testing tools.
• Work closely with product, engineering, and leadership teams to identify quality risks, communicate insights and metrics, and proactively enhance the customer experience.
• Provide strategic and tactical engineering and architecture leadership, develop delivery and resource plans, create roadmaps, and drive operational excellence.
• Optimize operating costs and budgets by reducing technical debt, offering improved risk visibility through executive‑level reporting, and coordinating all program‑related activities.
• Guide planning and execution of projects and programs, establish technical and functional standards and practices, and oversee processes, procedures, career development, and skillset mapping.
• Define objectives and key results (OKRs), return on investment (ROI), and key performance indicators (KPIs) and deliver reports on metrics with recommendations for improved delivery.
• Collaborate with business stakeholders to ensure a clear and actionable engineering backlog and remove blockers for senior leadership.
• Participate in annual budgeting, capital processes, and quality improvement activities for the organization.
• Provide guidance on principles, practices, and techniques relevant to the application area and organization.
• Provide feedback to address performance gaps, including functional, technical, and soft skills.
• Actively participate in recruitment and selection processes for both CVS and vendor candidates, and lead relationships with onsite and offshore vendors.
• Ensure all teams adhere to the highest standards of integrity and the Code of Conduct.

• 10+ years of Information Technology experience across various technological platforms, including leadership and development management experience.
• 10+ years of experience translating complex testing and automation strategies into strategic business outcomes.
• 5+ years of experience leveraging AI technologies and testing and automation techniques for validating these technologies, including unit, integration, quality and model testing, regression, and performance validation in a high‑performance Agile environment.
• 5 years focused on cloud‑native environments (i.e. IBMi AS400, GCP, and Azure highly preferred).
• 4+ years of hands‑on development experience across multiple technological platforms.
• Bachelor's degree or equivalent experience.

• Executive‑level communication skills with the ability to effectively articulate strategic concepts to…