AI ML Engineering Jobs in Massachusetts

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.

Position Summary

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.

Job Duties

Portfolio Ownership & Business Impact

• 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

AI Strategy

• 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

Technical Leadership

• 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

People & Delivery Leadership

• 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

Stakeholder Partnership

• 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

Security, Compliance & Data Governance

• 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

Required Qualifications

• 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

Education

Bachelor's degree or equivalent work experience in Mathematics, Statistics, Computer Science, Analytics, Engineering, or related discipline. Master's degree preferred

Preferred Qualifications

• 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

Pay Range

The typical pay range for this role is:

$144,200.00 - $288,400.00

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 full-time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well-being 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: 08/31/2026

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