Lead Director – Software Engineering, Health100 Platform

This is a fully remote position, open to applicants in Illinois, +3 more states.

📋 Description

• Define and lead product and technical roadmaps that encompass multi-team efforts in cross-platform app development, platform APIs, and AI agent functionalities.

• Establish architectural guidance for multi-agent orchestration, integration of MCP tools and data, RAG pipelines, LLM infrastructure, and distributed systems.

• Align engineering investments across backend, mobile/web, and AI/ML domains with desired business outcomes.

• Create scalable engineering standards and operational frameworks for full-stack applications and AI agent systems.

• Develop AI-specific risk management strategies addressing model drift, hallucination, safety guardrails, data privacy, prompt injection, and agent routing accuracy.

• Enhance observability and assessment for both traditional systems and AI agents.

• Mentor and lead engineering managers and senior engineers in backend, cross-platform applications, and applied AI/agent fields.

• Oversee hiring, performance management, career progression, and succession planning initiatives.

• Collaborate with Product, Business, Architecture, Design, Security, and executive leadership to convert strategy into actionable programs.

• Articulate complex technical and AI architecture to both technical and non-technical stakeholders.

• Manage strategies for vendor and contingent workforce engagement.

• Spearhead technology research and innovation initiatives in AI/agents, cloud computing, application frameworks, and distributed systems.

• Remain updated on emerging standards and integrate beneficial technologies into the roadmap.

⛳️ Requirements

• Over 12 years of experience in software engineering.

• More than 5 years of experience leading managers and senior engineers in Agile, cloud-native settings.

• Proven track record in delivering large-scale, multi-team engineering projects that include backend platforms, native mobile and cross-platform applications, and AI-driven functionalities.

• Strong technical expertise in distributed systems and cloud-native architecture.

• Proficiency in microservices with Java/Spring Boot and Python.

• Familiarity with DevOps practices, CI/CD processes, Kubernetes, and Docker.

• Experience with cloud platforms, with a preference for GCP.

• Documented success in building and scaling high-performing engineering teams, including managing distributed teams and vendor collaborations.

• Exceptional communication and influence skills at the executive level.

• At least 1 year of experience in delivering AI-enabled or generative AI-integrated software.

• Preferred experience in agent-based architectures, tool-use/function calling, or protocols such as MCP.

• Bachelor's degree in Computer Science, Information Systems, Engineering, a related field, or equivalent experience.

• High school diploma plus 4 years of relevant work experience is accepted as an alternative qualification.

🏝️ Benefits

• CVS Health bonus, commission, or short-term incentive program.

• Award target within the company’s equity award program.

• Comprehensive medical coverage.

• Dental coverage.

• Vision coverage.

• Paid time off.

• Retirement savings options.

• Wellness programs.

• Additional resources supporting physical, emotional, and financial well-being.

• Comprehensive benefits package for eligible full-time employees and their families.