Lead Director, Software Engineering

CVS Health•Hartford, CT

23h•$144,200 - $288,400

About The Position

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 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's done it at the highest levels of the industry. You will set the bar — and then raise it.

Requirements

10+ years of progressive software engineering experience, including 5+ years leading large-scale engineering organizations.
You have built and scaled systems that serve tens of thousands of users. You know what happens when your system goes down.
Deep, hands-on technical foundation in distributed systems, cloud-native architectures, and modern backend engineering at scale.
Proven AI platform ownership. You have deployed production AI systems - not POCs, not demos, not limited to prompt engineering. You understand model deployment pipelines, vector databases, RAG architectures, LLM orchestration, inference optimization, and responsible AI principles.
Track record of engineering transformation. You have migrated monoliths to microservices, modernized legacy platforms under real business pressure, and lived the consequences of every architectural decision you've made.
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.

Nice To Haves

Healthcare or highly regulated domain experience — You have navigated HIPAA, CMS compliance, PHI data handling development.
Platform engineering ownership — You have built or led internal developer platforms, engineering productivity tooling.
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 gives us confidence in your technical ceiling.

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 you make should start with the question: How to create10x leverage?
You will actively embed LLMs, generative AI, agentic workflows, and ML-powered automation into the engineering lifecycle, not just as experiments, but as production-grade differentiators.
Own delivery at velocity. You ship. You are accountable for outcomes, not roadmaps. You hold your teams to the same standard.
Partner at the executive level — with Product owners, Data Engineers, and Health care business leaders — translating business strategy into engineering bets with precision and conviction.
Be the technical voice in the room You call out architectural debt, push back on infeasible timelines, and advocate for the right engineering investment.