Principal Software Development Engineer

CVS Health

5d

About The Position

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time. 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.

Requirements

• 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/DevOps environments with CI/CD best practices.
• 3+ years of programming experience in Kotlin, contributing to production-grade services.

Nice To Haves

• 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".

Responsibilities

• 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

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Number of Employees: 5,001-10,000 employees