Principal Software Development Engineer

Position Summary

Oak Street Health is a critical part of healthcare delivery. Our platform is essential to enabling our value-based care model and integral to how our providers take care of their patients. This platform includes our core domain services, the Canopy platform, our data and analytics platform, and much more. At Oak Street Health, you will be influential in the development of innovative products that do more than just building scalable services.

Everything you do will have an immediate impact on the health and wellbeing of our patients.

As a Principal Software Development Engineer, you will have an impactful contribution in the delivery of a new kind of platform for healthcare, one built specifically for the clinical team. From design to implementation, you will partner with our stellar engineering, product, and design teams in a fast-paced, agile environment to transform ideas into a reality. Utilizing modern methodologies and open source tools, you will be empowered to push the boundaries of development as we seek to deliver applications that will directly and immediately impact the experience of our teams and our patients.

There is no better time to join our rapidly growing team at Oak Street Health. We can’t think of a mission any more motivating; and, with your help, we can drive change in healthcare for the patients that need us most.

• Develop and maintain cloud‑native microservices using Java, Spring Boot, and Kotlin
  , with event‑driven integrations built on Kafka and deployed in Azure environments (AKS, ACA, ACR).

• Lead the architectural vision and system design for the entire engineering department using a modern technology stack with a core focus on reusability, scalability and performance at scale

• Collaborate with Senior Management & Product Leaders in driving technology roadmaps and execution

• Guide engineering teams in anticipation of future use cases and helps them make design decisions

• Contribute to improving our Engineering processes, i.e. agile methodology, CI/CD, devops, security and quality initiatives

• Ensure Oak Street’s Technology initiative OKR’s are aligned across teams supporting business needs

• Other duties as assigned

• 10 years of experience building consumer‑facing products and developing RESTful API services using JVM‑based technologies
  .

• 8 years of hands-on programming experience in Java and Spring Boot
  , delivering scalable, maintainable microservices.

• 8 years of experience designing and operating distributed systems in a cloud environment
  , preferably Azure (open to AWS or GCP).

• 6 years of expertise with a “design‑first” approach
  , including documenting technical designs and decomposing architecture into actionable stories for engineering teams.

• 5 years of experience with Kafka and event-driven architectures
  , including topics, partitions, schema management, and consumer group patterns.

• 5 years of experience leading Agile teams and delivering products in Agile/Dev Ops environments with CI/CD best practices.

• 3 years of programming experience in Kotlin
  , contributing to production-grade services.

• Excellent communication skills
  , with the ability to collaborate effectively with cross‑functional business partners
  , influence decision‑making, and translate technical concepts for non‑technical audiences.

• Hands‑on experience with Python in a data engineering environment
  , including data processing, pipelines, or integration with analytics/ML workflows.

• Experience leveraging AI and Large Language Models (LLMs) —such as Cursor, Google Gemini, and OpenAI —to automate workflows, enhance developer productivity, or integrate intelligent features into engineering solutions.

• Someone who embodies being “Oaky”.

• Bachelor’s degree in Computer Science or related degree required

The typical pay range for this role is:

$ – $

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is…