Lead Director, AI/ML Engineering

CVS Health•Hartford, CT

2d•$144,200 - $288,400

About The Position

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.

Requirements

Bachelor's degree in Computer Science, Information Technology, Engineering, or a related field
10+ years of experience in technical roles within software engineering, data engineering, or analytics
5+ years designing and building data and analytics solutions, including Data/ML pipelines, products, or decision systems at scale
5+ years deploying cloud-native applications on Azure, GCP, or AWS, with working knowledge of modern Data & AI Ops patterns
3+ years leading and growing engineering teams delivering complex, production-grade analytical systems
Demonstrated ability to engage in technical architecture and design conversations, including trade-off analysis and solution design
Hands-on experience with MCP server development, Claude Skills Framework, LLM integration, or agentic AI frameworks applied to enterprise workflows
Experience operating in agile delivery frameworks (Scrum, Squad model, or equivalent)
Experience in CI/CD and DataOps practices
Strong executive communication skills with demonstrated ability to influence senior stakeholders across technical and business teams
Bachelor's degree or equivalent work experience in Mathematics, Statistics, Computer Science, Analytics, Engineering, or related discipline.

Nice To Haves

Master's degree preferred
Familiarity with open-source ML orchestration frameworks (e.g., Kubeflow, MLflow, Airflow) and model lifecycle management
Experience with Claude AI Skills engineering (SKILL.md, YAML metadata, execution scripts) or Agent Orchestration frameworks such as LangChain , LangGraph , or equivalent
Background in Retail or health care context
Exposure to prompt engineering, system instruction authoring, and natural language workflow tuning for enterprise AI platforms
Data platforms: Snowflake or BigQuery
Exposure to Databricks, Dataproc, or equivalent
Advanced degree (Master's or PhD) in a business, quantitative, or technical discipline

Responsibilities

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 development and inclusion
Serve as a trusted technology partner to senior stakeholders across Data Science, Business, and Enterprise Technology teams
Translate complex technical concepts — including agentic AI architectures, MCP integrations, Claude Skills Framework, and LLM optimization strategies — into clear, business-relevant narratives for Executive and non-technical audiences
Ensure all data interactions and AI-driven workflows operate in strict adherence to CVS Health's enterprise data governance policies, HIPAA requirements, authentication standards, and role-based access controls
Partner closely with Information Security and Compliance teams to embed governance into every layer of the AI/ML platform