Lead Director, AI​/ML Engineering

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.

As Lead Director of Data Analytics and AI/ML Engineering at CVS Health, you will own a high-impact portfolio of Data, AI, and ML products driving CVS Retail Pharmacy Growth, Store Operations and Profitability Analytics and AI Engineering. This role sits at the intersection of technology and product delivery — leading architecture, driving execution, growing a high-performing team, and engaging senior stakeholders across Data Science, Business, and Technology organizations.

You will advance CVS Health's AI strategy from enterprise LLM adoption to purposeful, agentic automation — delivering scalable solutions that measurably improve operations and health outcomes across our lines of business. The ideal candidate is a seasoned AI leader with technical depth in Data, AI/ML, MCP (Model Context Protocol), Claude Skills Framework, and cloud-native development — with a proven track record of delivering analytically complex, large-scale products that create lasting value for our patients, customers, and colleagues.

• Own a Data, AI/ML product portfolio spanning Growth and Pharmacy Store Operations — delivering insights that advance CVS Health's mission of helping people on their path to better health
• Define and drive the technical roadmap, balancing bold innovation with agile delivery, operational stability, and reliability at enterprise scale

• Define and lead our AI roadmap, architecting the strategic shift from general-purpose LLM deployment to intelligent, agentic automation that drives measurable operational and health outcomes across lines of business
• Lead the strategic shift from rule-based process to AI and agent-based orchestration, enabling intelligent, autonomous workflows across CVS Health's lines of business
• Spearhead the adoption and scaling of the Claude Skills Framework — establishing governance, design standards, and reusable patterns that enable consistent, enterprise-wide AI skill development
• Design and oversee modular Claude Skill modules (SKILL.md, YAML metadata, and execution scripts) to automate high-impact business processes including pharmacy reporting, code deployment workflows
• Champion progressive disclosure strategies for LLM context optimization — mapping specialized Claude Skills to targeted triggers to maximize precision, minimize latency, and deliver scalable enterprise value
• Evaluate emerging agentic AI technologies and frameworks, translating innovations into actionable roadmap investments aligned with CVS Health's strategic priorities

• Architect and oversee the end to end development of Data and ML/AI products following CVS security principles.
• Establish engineering standards and best practices across MCP integrations and Claude Skills Framework development — ensuring consistency, reusability, and alignment with CVS Health's security, data governance, and HIPAA compliance requirements
• Lead hands‑on architecture reviews, technical design forums, and solution trade‑off discussions across Data Science, Engineering, and Technology teams
• Lead end‑to‑end AI/ML pipeline integrity — from Claude Skills authoring and MCP server deployment through to production monitoring and continuous optimization
• Ensure engineering standards are maintained across the portfolio — covering solution design, security, and Data/AI Ops practices

• Drive agile delivery within CVS Health's Squad model, managing dependencies across a matrixed environment and removing blockers to accelerate delivery
• Coach and grow engineering leaders and senior individual contributors, building a strong internal talent pipeline that reflects CVS Health's commitment to colleague…