Senior Director, Software Engineering — AI Platform

9025 CVS Shared Services Resources LLC; Wellesley (MA); On-site; USD 144,000 - 288,000; Full time

Benefits offered by this job

Comprehensive benefits

Bonus & equity

Paid time off

Wellness programs

Retirement savings options

Job summary

CVS Health is seeking a Lead Director of Software Engineering to set architectural standards and elevate engineering excellence across a large multi-team organization. You will drive AI-enabled modernization, oversee production systems, and partner with health care leaders to translate strategy into concrete engineering bets.

You will own delivery velocity, push for feasible timelines, and shape the technical voice in executive discussions, ensuring responsible AI practices and scalable

Qualifications

• 10+ years of progressive software engineering experience.
• 5+ years leading large-scale engineering organizations.
• Deep, hands-on foundation in distributed systems, cloud-native architectures, and backend engineering at scale.
• Proven AI platform ownership: deployed production AI systems, model deployment pipelines, vector databases, RAG architectures, LLM orchestration, inference optimization, and responsible AI principles.

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 engineering lifecycle as production-grade differentiators.
• Own delivery at velocity, accountable for outcomes; hold teams to the standard.
• Partner with Product, Data Engineers, and Health care leaders to translate strategy into engineering bets.
• Be the technical voice, highlight architectural debt and advocate for investments.

Job description

CVS Health is seeking a Lead Director of Software Engineering to set architectural standards and elevate engineering excellence across a large multi-team organization. You will drive AI-enabled modernization, oversee production systems, and partner with health care leaders to translate strategy into concrete engineering bets.

You will own delivery velocity, push for feasible timelines, and shape the technical voice in executive discussions, ensuring responsible AI practices and scalable