Senior Director, AI-Driven Software Engineering

CVS Health; Saint Paul (MN); On-site; USD 144,000 - 288,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Paid time off

Retirement plan

Wellness programs

Equity awards

Job summary

CVS Health is seeking a Lead Director of Software Engineering to drive the technical strategy for a multi-team organization and elevate engineering standards. You will own delivery velocity, oversee AI-powered initiatives, and partner with business and health leaders to translate strategy into engineering bets.

The role demands a strong foundation in distributed systems, cloud-native architectures, and production AI systems, with a track record of transforming monoliths to microservices.

Qualifications

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

Responsibilities

• Drive technical strategy across a multi-team engineering org (50-150+ engineers).
• Embed LLMs, AI, agentic workflows, and ML-powered automation into the lifecycle.
• Own delivery at velocity and hold teams to outcomes, not roadmaps.
• Partner with Product, Data, and Health care leaders to translate strategy into engineering bets.
• Advocate for the right engineering investments and push back on infeasible timelines.

Skills

Distributed systems

Cloud-native architectures

AI platform ownership

Leadership at scale

MLOps / AI integration

Tools

Vector databases

RAG architectures

LLM orchestration

Job description

CVS Health is seeking a Lead Director of Software Engineering to drive the technical strategy for a multi-team organization and elevate engineering standards. You will own delivery velocity, oversee AI-powered initiatives, and partner with business and health leaders to translate strategy into engineering bets.

The role demands a strong foundation in distributed systems, cloud-native architectures, and production AI systems, with a track record of transforming monoliths to microservices.