Principal Software Development Engineer

Description

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 software 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.

Core Responsibilities :

Leads 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

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

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

Ensures Oak Street's Technology initiative OKR’s are aligned across teams supporting business needs

Other duties as assigned

What are we looking for?

We’re looking for a professional with :

Bachelor’s degree in CS or related degree / industry experience

Experience leading an agile team in delivering products

10+ years of experience building consumer-facing products using any SPA frameworks (Angular / React / Vue) and building restful API Services using JVM-based technologies (Kotlin or Java), or .NET APIs running in the cloud

Expert in distributed systems, cloud-based environment either in Azure / AWS using Docker / Kubernetes

Expert in “design first,” documenting technical designs, and being able to decompose the design into consumable stories for your team.

Must have experience with event-driven architecture, with Kafka being preferred.

Excellent communication skills and ability to work with cross functional business partners

Experience working in an Agile / Devops environment

Familiarity with our tech stack – JVM-based technologies, Spring Boot, .NET, Kubernetes, Kafka, MongoDB, OpenAPI, Protobuf - Preferred

US work authorization

Someone who embodies being “Oaky”

Pay Range

The typical pay range for this role is :

$144,200.00 - $288,400.00

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 eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in our comprehensive and competitive mix of pay and benefits – investing in the physical, emotional and financial wellness of our colleagues and their families to help them be the healthiest they can be. In addition to our competitive wages, our great benefits include :

Affordable medical plan options, a 401(k) plan (including matching company contributions), and an employee stock purchase plan .

No-cost programs for all colleagues including wellness screenings, tobacco cessation and weight management programs, confidential counseling and financial coaching.

Benefit solutions that address the different needs and preferences of our colleagues including paid time off, flexible work schedules, family leave, dependent care resources, colleague assistance programs, tuition assistance, retiree medical access and many other benefits depending on eligibility.

For more information, visit

We anticipate the application window for this opening will close on : 01 / 26 / 2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.