Oak Street Health Software Engineer Interview Questions + Guide in 2025

Oak Street Health is dedicated to transforming healthcare for older adults on Medicare by providing personalized primary care that prioritizes health outcomes over service volume.

As a Software Engineer at Oak Street Health, you will play a crucial role in the design and development of innovative healthcare technology solutions that enhance the patient experience. You will be responsible for contributing to the entire software development lifecycle (SDLC), including design, coding, testing, deployment, and maintenance, utilizing modern methodologies and technologies. Collaboration will be key, as you will work alongside cross-functional teams, including product managers and UX designers, to build highly available, scalable, and responsive services and APIs.

Your technical expertise in .NET Core and experience with cloud environments (such as Azure or AWS) will enable you to build cloud-native microservices that drive the performance of the Canopy platform. You will also mentor junior engineers and ensure adherence to best practices in coding and architecture.

The ideal candidate should possess a strong background in software engineering, with a minimum of 6 years of experience in building large consumer-facing products. A proactive attitude that embodies Oak Street’s values, known as being 'Oaky', is essential. This includes radiating positive energy, assuming good intentions, and taking ownership of results to deliver an unmatched experience for patients.

This guide will equip you with insights into the specific skills and experiences Oak Street Health values in a Software Engineer, helping you prepare effectively for your interview and stand out as a candidate who aligns with the company's mission and culture.

The interview process for a Software Engineer at Oak Street Health is structured to assess both technical skills and cultural fit within the organization. It typically consists of multiple rounds, each designed to evaluate different aspects of your qualifications and alignment with the company's mission.

1. Initial Phone Screen

The process begins with an initial phone screen, usually conducted by a recruiter or hiring manager. This conversation is generally straightforward, focusing on your resume, background, and motivations for applying to Oak Street Health. Expect to discuss your previous experiences and how they relate to the role, as well as your understanding of the company’s mission and values.

2. Technical Interview

Following the initial screen, candidates typically participate in a technical interview. This may involve a one-on-one session with an engineer where you will be asked to explain the behavior of .NET code and discuss your experience with various technologies. You might also encounter questions related to data manipulation and problem-solving scenarios relevant to the role. Be prepared to demonstrate your technical knowledge and coding skills, particularly in .NET and related frameworks.

3. Panel Interview

The next step often includes a panel interview, where you will meet with multiple team members, including senior engineers and possibly management. This format allows interviewers to assess your technical abilities and collaborative skills. Expect to discuss your approaches to scaling problems, architectural decisions, and how you would contribute to the team’s projects. This round may also include behavioral questions to gauge your fit within the company culture.

4. Final Interview

The final interview typically involves a more in-depth discussion with key stakeholders, such as the hiring manager and senior leadership. This round may include a case study or problem-solving session where you will be asked to address a current issue faced by Oak Street Health. This is an opportunity to showcase your critical thinking and how you would apply your skills to real-world challenges within the organization.

Throughout the process, candidates should be prepared for a thorough evaluation of their technical expertise, problem-solving abilities, and alignment with the company’s values.

As you prepare for your interviews, consider the types of questions that may arise in each round, focusing on both technical and behavioral aspects.

Here are some tips to help you excel in your interview.

Prepare for Multiple Rounds

The interview process at Oak Street Health can involve several rounds, often up to four. Be ready to engage in multiple discussions that may cover both technical and behavioral aspects. Approach each round with the mindset that you are not just being evaluated, but also assessing if the company aligns with your values and career goals. Prepare to articulate your motivations for applying and how your skills can contribute to their mission of improving healthcare.

Master the Technical Fundamentals

Given the emphasis on .NET technologies, ensure you have a solid grasp of .NET Core, APIs, and microservices architecture. Be prepared to discuss specific coding scenarios, such as memory management in .NET or data sharing between microservices. Familiarize yourself with the tech stack mentioned in the job description, including Azure, Docker, and Kafka, as these are likely to come up in technical discussions.

Embrace a Collaborative Mindset

Oak Street Health values collaboration across teams, so be prepared to discuss your experiences working in cross-functional environments. Highlight instances where you partnered with product managers, UX designers, or other engineers to deliver successful projects. Demonstrating your ability to work well with others will resonate with their team-oriented culture.

Showcase Problem-Solving Skills

Expect to encounter problem-solving scenarios during your interviews. You may be asked to work through a case study or technical challenge that reflects real issues faced by the company. Practice articulating your thought process clearly and logically, as this will demonstrate your analytical skills and ability to tackle complex problems.

Be Authentic and 'Oaky'

Oak Street Health seeks candidates who embody their 'Oaky' values, which include radiating positive energy and taking ownership. During your interviews, let your personality shine through. Share stories that reflect your commitment to creating positive experiences, whether for patients or team members. This authenticity will help you connect with your interviewers and show that you align with the company culture.

Prepare Thoughtful Questions

At the end of your interviews, you will likely have the opportunity to ask questions. Use this time to inquire about the team dynamics, ongoing projects, or how the company measures success in its mission. Thoughtful questions not only demonstrate your interest in the role but also provide you with valuable insights into whether Oak Street Health is the right fit for you.

By following these tips, you will be well-prepared to navigate the interview process at Oak Street Health and showcase your potential as a Software Engineer. Good luck!

In this section, we’ll review the various interview questions that might be asked during a Software Engineer interview at Oak Street Health. The interview process will likely assess your technical skills, problem-solving abilities, and cultural fit within the organization. Be prepared to discuss your experience with .NET technologies, cloud environments, and your approach to software development in a healthcare context.

Technical Skills

1. Can you explain how you would share data between microservices?

Understanding microservices architecture is crucial for this role, as it involves building scalable applications.

How to Answer

Discuss the various methods of inter-service communication, such as REST APIs, message brokers, or event-driven architectures. Highlight your experience with specific technologies that facilitate this.

Example

“I typically use REST APIs for synchronous communication between microservices, ensuring that each service is independently deployable. For asynchronous communication, I prefer using message brokers like Kafka, which allows for decoupling services and improving scalability.”

2. How does .NET manage memory?

This question tests your understanding of memory management in .NET, which is essential for building efficient applications.

How to Answer

Explain the garbage collection process in .NET and how it helps manage memory automatically, while also mentioning any manual memory management techniques you might use.

Example

“.NET uses a garbage collector to manage memory, which automatically frees up memory that is no longer in use. However, I also pay attention to memory leaks by implementing IDisposable for unmanaged resources and using weak references when necessary.”

3. What is an index, and why is it important in databases?

Indexes are critical for optimizing database queries, and understanding them is vital for a software engineer.

How to Answer

Define what an index is and explain how it improves query performance by allowing the database to find data more quickly.

Example

“An index is a data structure that improves the speed of data retrieval operations on a database table. It works similarly to an index in a book, allowing the database to locate rows more efficiently, which is crucial for maintaining performance in large datasets.”

4. Describe your experience with unit and integration testing.

Testing is a key part of the software development lifecycle, and your approach to it will be scrutinized.

How to Answer

Discuss the importance of testing in ensuring code quality and reliability, and mention specific frameworks or tools you have used.

Example

“I prioritize writing unit tests using xUnit to ensure that individual components function correctly. For integration testing, I use tools like Postman to verify that different services interact as expected, which helps catch issues early in the development process.”

5. How do you approach code reviews?

Code reviews are essential for maintaining code quality and fostering collaboration among team members.

How to Answer

Explain your philosophy on code reviews, including how you provide constructive feedback and learn from others.

Example

“I view code reviews as a collaborative learning opportunity. I focus on providing constructive feedback that emphasizes best practices and code readability, while also being open to suggestions from others to improve my own coding skills.”

Problem-Solving and Design

1. Can you walk us through a challenging technical problem you solved?

This question assesses your problem-solving skills and ability to navigate complex situations.

How to Answer

Choose a specific example that highlights your analytical skills and the steps you took to resolve the issue.

Example

“In a previous project, we faced performance issues due to a bottleneck in our API. I analyzed the request patterns and identified that we could optimize our database queries. By implementing caching and optimizing our SQL queries, we reduced response times by over 50%.”

2. How do you ensure your applications are scalable?

Scalability is crucial in healthcare applications, where user demand can vary significantly.

How to Answer

Discuss design patterns, architectural choices, and technologies you use to build scalable applications.

Example

“I focus on microservices architecture, which allows each service to scale independently based on demand. Additionally, I leverage cloud services like Azure to automatically scale resources and use load balancers to distribute traffic effectively.”

3. What is your experience with Agile methodologies?

Agile practices are common in software development, and your familiarity with them will be important.

How to Answer

Describe your experience working in Agile teams, including specific roles you’ve played and how you’ve contributed to the process.

Example

“I have worked in Agile teams for several years, participating in daily stand-ups, sprint planning, and retrospectives. I find that Agile methodologies foster collaboration and adaptability, allowing us to respond quickly to changing requirements.”

4. How do you handle technical debt in your projects?

Managing technical debt is essential for maintaining code quality over time.

How to Answer

Explain your approach to identifying, prioritizing, and addressing technical debt in your work.

Example

“I regularly assess our codebase for technical debt during code reviews and sprint planning. I prioritize addressing high-impact areas and advocate for allocating time in our sprints to refactor and improve code quality.”

5. Describe a time when you had to mentor a junior engineer.

Mentoring is an important aspect of leadership in software engineering.

How to Answer

Share a specific instance where you guided a junior engineer, focusing on your approach and the outcome.

Example

“I mentored a junior engineer who was struggling with understanding our codebase. I organized pair programming sessions to walk them through the architecture and best practices, which not only helped them gain confidence but also improved their contributions to the team.”