Drimva

CVS Health

Lead Director - Software Engineering

$144K–$288K

MA - Wellesley +30 · Remote/Hybrid · Director · Full-time · Posted Sep 25, 2026

Location
MA - Wellesley
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Experience
10+ years of progressive software engineering experience, including 5+ years leading large-scale engineering organizations.
Education
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 in a related field.

About the job

Leads technical strategy and delivery across a large software engineering organization, modernizing systems and deploying production AI capabilities.

What you'll do

  • Set architectural standards and engineering practices across a multi-team organization; review and elevate technical work.
  • Embed LLMs, generative AI, agentic workflows, and ML-powered automation into production engineering processes.
  • Own delivery outcomes and partner with executives and business leaders to turn strategy into engineering investments.

What they ask for

  • 10+ years of progressive software engineering experience, including 5+ years leading large-scale engineering organizations.
  • Hands-on expertise in distributed systems, cloud-native architectures, and modern backend engineering at scale.
  • Production AI platform ownership, including model deployment pipelines, vector databases, RAG, LLM orchestration, inference optimization, and responsible AI.
  • Track record of engineering transformation, including monolith-to-microservices migrations and legacy platform modernization.

Nice to have

  • Healthcare or highly regulated domain experience, including HIPAA, CMS compliance, or PHI data handling.
  • Platform engineering ownership, including internal developer platforms or engineering productivity tooling.

Pay

$144,200.00 - $288,400.00 USD base salary

Tools

LLMs, generative AI, agentic workflows, ML-powered automation, vector databases, RAG, microservices

AI focus

Deploy production AI systems and integrate LLMs, generative AI, agentic workflows, and ML-powered automation into the engineering lifecycle.

Model-written summary · the original posting is authoritative

First seen Oct 14, 2026 · Last verified Nov 5, 2026 (UTC)