Director of AI-Driven Software Engineering

CVS Health; Wellesley (MA); On-site; USD 144,000 - 288,000; Full time

Benefits offered by this job

Medical coverage

Dental coverage

Vision coverage

Retirement savings options

Job summary

CVS Health is seeking a Lead Director of Software Engineering to set the bar for technical excellence and lead a large-scale engineering organization. You will guide architecture, review critical work, and drive AI-powered transformations across teams.

You’ll partner with Product and Health care leaders to translate business strategy into engineering bets, owning delivery and outcomes in a high-impact environment. Competitive benefits included.

Qualifications

• 10+ years of progressive software engineering experience, including 5+ years leading large-scale engineering organizations.
• Deep, hands-on foundation in distributed systems, cloud-native architectures, and modern backend engineering at scale.
• Proven AI platform ownership with production AI systems, including model deployment pipelines.
• Track record of migrating monoliths to microservices and modernizing legacy platforms.

Responsibilities

• Drive technical strategy across a multi-team engineering organization (50-150+ engineers), defining standards and elevating work.
• Embed LLMs, generative AI, agentic workflows, and ML-powered automation into the engineering lifecycle as production-grade differentiators.
• Own delivery at velocity and be accountable for outcomes, not roadmaps.
• Partner at the executive level with Product, Data Engineers, and healthcare business leaders to translate strategy into engineering bets.
• Be the technical voice, call out architectural debt, and advocate for the right engineering investments.

Skills

Leadership

Distributed systems

Cloud-native

Backend engineering

AI platform ownership

Model deployment

LLM orchestration

Microservices

Architectural debt

Tools

Vector databases

RAG architectures

Job description

CVS Health is seeking a Lead Director of Software Engineering to set the bar for technical excellence and lead a large-scale engineering organization. You will guide architecture, review critical work, and drive AI-powered transformations across teams.

You’ll partner with Product and Health care leaders to translate business strategy into engineering bets, owning delivery and outcomes in a high-impact environment. Competitive benefits included.