Director, Software Engineering

You are driven to transform healthcare through software and believe that primary care, when powered by the right technology, can deliver dramatically better outcomes at lower cost. You are motivated by solving messy, real-world problems and turning them into scalable, elegant systems.

You operate with high ownership and high judgment. You are as comfortable writing production code as you are making architectural tradeoffs and prioritization decisions alongside business leaders. You thrive in ambiguity, move quickly, and care deeply about building things that actually work in the hands of end users.

You are not just an engineering leader. You are a builder, a systems thinker, and a partner to the business.

Your Role

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.

Core Expectations

Technical Leadership & Architecture

• 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

AI-Native Product Development

• 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

Cloud, DevSecOps & Platform Operations

• 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

Business Translation & Team Building

• 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

Key Responsibilities

• The provider enablement platform, including patient- and provider-facing applications
• Integrations across multiple EMRs and external data sources
• Secure, compliant architecture aligned to HIPAA, SOC 2, and HITRUST
• Engineering execution: roadmap translation, milestone planning, and delivery

In Your First 12 Months, You Will

• 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

What We’re Looking For

Required:

• 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

Strongly Preferred:

• 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