Senior Director, Software Engineering - AI & Scale

CVS Health; Richmond (VA); On-site; USD 144,000 - 288,000; Full time

Job summary

CVS Health seeks 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.

You will drive technical strategy across a multi-team engineering organization (50–150+ engineers), embed generative AI, agentic workflows, and ML-powered automation into the lifecycle, and own delivery at velocity with outcomes over roadmaps.

Qualifications

• 10+ years of progressive software engineering experience.
• 5+ years leading large-scale engineering organizations.
• Deep knowledge of distributed systems and cloud-native architectures.
• Production AI experience: model deployment, pipelines, and responsible AI.

Responsibilities

• Drive technical strategy across a multi-team engineering organization (50-150+ engineers).
• Embed LLMs, generative AI, agentic workflows, and ML-powered automation into the lifecycle.
• Own delivery at velocity and be accountable for outcomes.
• Partner with Product owners, Data Engineers, and Health care leaders to translate business strategy into engineering bets.
• Be the technical voice, advocate for the right engineering investments.

Skills

Technical leadership

Distributed systems

AI platforms

Engineering transformation

Tools

Vector databases

LLM orchestration

RAG architectures

Inference optimization

Job description

CVS Health seeks 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.

You will drive technical strategy across a multi-team engineering organization (50–150+ engineers), embed generative AI, agentic workflows, and ML-powered automation into the lifecycle, and own delivery at velocity with outcomes over roadmaps.