Lead Director – Software Engineering, Health100 Platform

Job Description:

  • Define and drive multi-team product and technical roadmaps spanning cross-platform app development, platform APIs, and AI agent capabilities
  • Set architectural direction for multi-agent orchestration, MCP tool/data integration, RAG pipelines, LLM infrastructure, and distributed systems
  • Align engineering investment across backend, mobile/web, and AI/ML disciplines with business outcomes
  • Establish scalable engineering standards and operational frameworks across full-stack apps and AI agent systems
  • Build AI-specific risk management practices covering model drift, hallucination, safety guardrails, data privacy, prompt injection, and agent routing accuracy
  • Drive observability and evaluation for traditional systems and AI agents
  • Lead, mentor, and grow engineering managers and senior engineers across backend, cross-platform app, and applied AI/agent disciplines
  • Own hiring, performance management, career development, and succession planning
  • Partner with Product, Business, Architecture, Design, Security, and executive leaders to translate strategy into executable programs
  • Communicate complex technical and AI architecture to technical and non-technical audiences
  • Manage vendor and contingent workforce strategies
  • Lead technology research and innovation across AI/agents, cloud, app frameworks, and distributed systems
  • Stay current with emerging standards and incorporate valuable technologies into the roadmap

Requirements:

  • 12+ years of software engineering experience
  • 5+ years leading managers and senior engineers in Agile, cloud-native environments
  • Proven delivery of large-scale, multi-team engineering programs spanning backend platforms, native mobile and cross-platform apps, and AI-driven features
  • Strong technical depth in distributed systems and cloud-native architectures
  • Experience with microservices using Java/Spring Boot and Python
  • Experience with DevOps, CI/CD, Kubernetes, and Docker
  • Experience with cloud platforms; GCP preferred
  • Demonstrated success building and scaling high-performing engineering organizations, including distributed teams and vendor partnerships
  • Executive-level communication and influence skills
  • 1+ year delivering AI-enabled or generative AI-integrated software
  • Experience with agent-based architectures, tool-use/function calling, or protocols such as MCP is preferred
  • Bachelor's degree in Computer Science, Information Systems, Engineering, related field, or equivalent experience
  • High school diploma plus 4 years of relevant work experience accepted as an alternative

Benefits:

  • CVS Health bonus, commission or short-term incentive program
  • Award target in the company’s equity award program
  • Medical coverage
  • Dental coverage
  • Vision coverage
  • Paid time off
  • Retirement savings options
  • Wellness programs
  • Other resources supporting physical, emotional, and financial well-being
  • Comprehensive benefits package for eligible full-time colleagues and their families
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