Director, Software Engineering

Oasis Health Partners•Chicago, IL

1d•$159,000 - $200,000

About The Position

Oasis Health Partners (Oasis) is building healthier communities by advancing primary care. We partner with patients, providers, and plans to provide personalized, local care for seniors. The Director, Software Engineering will report to the Vice President of Software Engineering and help build, operate, and scale our software engineering organization and technology platform. This is a hands-on, builder-first role. Initially, you should expect to spend ~80% of your time writing code, designing systems, and standing up core infrastructure. Over time, you will help hire and lead a small, high-leverage team, but this is not a traditional management-heavy role. We are intentionally building a lean engineering team and are looking for a player-coach who enjoys staying close to the technology while providing technical and operational leadership. Today’s value-based care (VBC) infrastructure is fragmented, reactive, and not built for the realities of modern care delivery. Providers are underserved by legacy tools that fail to integrate data, workflows, and decision-making in meaningful ways. Oasis is building a modern, AI-native platform to change that. You will partner closely with the VP of Software Engineering and work alongside Product, Data Engineering, and Security to help define and build Oasis’ next-generation provider enablement platform, including core application architecture, data integration strategy, and AI-native capabilities.

Requirements

10+ years of software engineering experience
4+ years in a technical leadership role (player-coach strongly preferred)
Proven track record of personally building and delivering production systems
Demonstrated experience using AI-powered solutions (i.e.: Claude Code) to deliver quality software solutions to production in a highly regulated environment
Demonstrated experience applying LLMs and/or agentic workflows in real-world applications
Deep expertise in AWS and modern cloud architecture
Strong full-stack experience (e.g., React/Angular + Node.js/TypeScript or similar)
Proficiency in Python and SQL
Experience designing APIs and integrating with complex external systems
Candidates must be authorized to work in the United States without a current or future visa sponsorship.
This role is open to applicants currently residing in the United States.

Nice To Haves

Experience building QA automation and reporting solutions
Experience building SRE solutions
Experience building healthcare or provider-facing applications
Experience working in HIPAA / SOC 2 / HITRUST environments
Background in startup or high-growth environments

Responsibilities

Partner with the VP of Software Engineering on architecture and technology strategy, staying hands-on in design, code review, and technical decisions
Evolve the architecture as the platform grows, and manage technical debt before it becomes a barrier
Set pragmatic standards that balance scalability, security, maintainability, delivery speed, and cost
Use AI-assisted development tools and agentic workflows to materially increase engineering velocity
Embed AI directly into provider workflows (documentation, decision support, care coordination), building systems where AI is foundational, not additive
Own the reliability, security, and operation of the AWS platform, including infrastructure-as-code, CI/CD, and QA automation
Establish monitoring, observability, SLOs/RTOs/RPOs, and incident response practices
Build runbooks so critical platform knowledge isn't siloed on one person
Work directly with clinical, operations, and growth teams to turn ambiguous real-world processes into scalable products, prioritized by ROI
Recruit and develop a small, high-performing engineering team, setting a high bar for quality, speed, and ownership
Contribute to the architecture and launch core components of Oasis’ provider platform
Implement initial QA automation, observability, and operational solutions and workflows
Contribute to agentic SDLC operations, maturing our use of AI to deliver high quality, maintainable software
Deliver production-grade patient and provider-facing applications
Implement initial AI-powered workflows within provider operations
Establish foundational engineering standards, infrastructure, and development velocity