Lead Director, Software Engineering (, CT, United States)

Position Summary

We’re looking for a Lead Director of Software Engineering who thinks like a founder, executes like a principal engineer, and leads like someone who has done it at the highest levels of the industry. You will set the bar—and then raise it.

Responsibilities

• Drive technical strategy across a multi‑team engineering organization (50–150+ engineers), setting architectural standards, defining engineering excellence benchmarks, and personally reviewing and elevating the work.
• Operational Efficiency: Every system design decision should start with the question: How to create 10x leverage? Embed LLMs, generative AI, agentic workflows, and ML‑powered automation into the engineering lifecycle as production‑grade differentiators.
• Own delivery at velocity; ship and be accountable for outcomes, not roadmaps.
• Partner at the executive level with Product owners, Data Engineers, and Health care business leaders to translate business strategy into engineering bets.
• Be the technical voice in the room: call out architectural debt, push back on infeasible timelines, and advocate for the right engineering investment.

Required Qualifications

• 10+ years of progressive software engineering experience, including 5+ years leading large‑scale engineering organizations.
• Built and scaled systems that serve tens of thousands of users and understand the implications of system downtime.
• Deep, hands‑on technical foundation in distributed systems, cloud‑native architectures, and modern backend engineering at scale.
• Proven AI platform ownership: deployed production AI systems, understood model deployment pipelines, vector databases, RAG architectures, LLM orchestration, inference optimization, and responsible AI principles.
• Track record of engineering transformation: migrated monoliths to microservices, modernized legacy platforms under real business pressure, and lived the consequences of every architectural decision.

Preferred Qualifications

• Healthcare or highly regulated domain experience navigating HIPAA, CMS compliance, and PHI data handling development.
• Platform engineering ownership: built or led internal developer platforms and engineering productivity tooling.

Education

Minimum: Bachelor’s degree in Computer Science, Software Engineering, Mathematics, or a closely related technical discipline—or equivalent demonstrated engineering depth through work history, open‑source portfolio, or verifiable technical contribution at scale. Preferred: Master’s degree (M.S. or M.Eng.) in Computer Science, Artificial Intelligence, Machine Learning, Data Science, or a related quantitative field. Graduate‑level training in algorithms, distributed systems, statistical learning, or systems design is a plus.

Pay

The typical pay range for this role is: $144,200.00 – $288,400.00. The actual base salary offer will depend on experience, education, geography and other factors. This position is eligible for a CVS Health bonus, commission or short‑term incentive program, and includes an equity award target.

Benefits

This full‑time position is eligible for a comprehensive benefits package that includes medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources as determined by eligibility.

EEO Statement

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