Oscar Insurance Software Engineer Interview Questions + Guide in 2025

Oscar Insurance is a pioneering health insurance company that integrates a full-stack technology platform with a commitment to serving its members effectively.

As a Software Engineer at Oscar, you will play a crucial role in developing and optimizing software solutions that enhance the healthcare experience. This position entails working closely with the Chief Architect and fellow engineers to build a robust claims system capable of processing over 10 million claims daily. You will apply machine learning techniques to detect fraudulent activities, ensuring the integrity of claims and driving cost efficiencies. Your responsibilities will also include troubleshooting large-scale technical challenges, improving data processing methodologies, and maintaining high system reliability and performance.

The ideal candidate will possess over five years of professional experience in software engineering, showcasing a proven track record of impactful contributions across various technologies. Candidates should demonstrate a strong grasp of computer science principles, be adept at proposing and experimenting with new technologies, and be passionate about constructing scalable, fault-tolerant systems. An ability to work independently while contributing effectively to team dynamics is essential.

This guide provides tailored insights that will equip you with the knowledge and confidence needed to excel in your interview with Oscar Insurance, helping you to effectively communicate your skills and experiences in alignment with the company’s mission and values.

The interview process for a Software Engineer at Oscar Insurance is structured to assess both technical skills and cultural fit within the company. It typically consists of several stages, each designed to evaluate different aspects of a candidate’s qualifications and compatibility with Oscar’s mission and values.

1. Initial Recruiter Call

The process begins with a phone call from a recruiter, which usually lasts about 30 to 45 minutes. During this call, the recruiter will discuss your background, interests, and motivations for applying to Oscar. They will also provide an overview of the company and the role, as well as set expectations for the next steps in the interview process. This is an opportunity for you to ask questions about the company culture and the specifics of the role.

2. Technical Phone Screen

Following the initial call, candidates typically undergo a technical phone screen. This interview lasts around 45 minutes and focuses on assessing your coding skills and problem-solving abilities. You will be asked to solve algorithmic problems, often using a collaborative coding platform. Expect questions that require you to demonstrate your understanding of data structures, algorithms, and possibly system design concepts. The interviewer may also ask follow-up questions to gauge your thought process and approach to problem-solving.

3. Onsite Interview

Candidates who perform well in the technical phone screen are invited for an onsite interview, which can be conducted in-person or virtually. This stage usually consists of multiple rounds, including technical interviews, a system design interview, and a culture fit assessment. The technical interviews will involve solving coding problems on a whiteboard or a shared coding environment, while the system design interview will assess your ability to architect scalable and reliable systems. Additionally, you may have a demo session where you can learn more about Oscar’s products and ask questions about the technology stack.

4. Final Interview and Debrief

The final stage often includes a debrief with the recruiter or hiring manager, where you can discuss your experience during the interview process and ask any remaining questions. This is also when you may receive feedback on your performance and learn about the next steps regarding an offer or further evaluations.

As you prepare for your interview, it’s essential to be ready for a mix of technical challenges and discussions about your past experiences and how they align with Oscar’s mission. Now, let’s delve into the specific interview questions that candidates have encountered during the process.

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

Understand the Company Culture

Oscar values a collaborative and innovative environment, so it’s essential to demonstrate your ability to work well in teams. Familiarize yourself with Oscar’s mission and how it aims to change healthcare. Be prepared to discuss how your values align with the company’s focus on serving its members and improving the healthcare experience. Showing genuine interest in the company and its products can set you apart from other candidates.

Prepare for Technical Challenges

Given the emphasis on solving complex technical problems, brush up on your coding skills, particularly in languages and technologies relevant to the role. Expect to encounter algorithmic questions that may require you to think critically and solve problems on the spot. Practice coding problems on platforms like LeetCode, focusing on medium to hard difficulty levels, as many candidates reported similar experiences. Be ready to explain your thought process clearly and concisely during coding interviews.

Be Ready for Behavioral Questions

Oscar’s interview process includes behavioral questions to assess cultural fit. Prepare to discuss your past experiences, particularly those that highlight your problem-solving skills, teamwork, and adaptability. Use the STAR (Situation, Task, Action, Result) method to structure your responses, ensuring you convey the impact of your contributions effectively.

Engage with Your Interviewers

During the interview, take the opportunity to ask thoughtful questions about the team, projects, and company culture. This not only shows your interest but also helps you gauge if Oscar is the right fit for you. Be prepared to discuss your interests, both work-related and personal, as interviewers appreciate candidates who can connect on a human level.

Manage Expectations and Follow Up

Given the feedback from candidates about delays in communication, it’s wise to manage your expectations regarding the timeline for feedback. After your interview, consider sending a follow-up email thanking your interviewers for their time and reiterating your interest in the position. This can help keep you top of mind as they make their decisions.

Stay Authentic

Lastly, be yourself. Oscar values authenticity and diversity, so don’t hesitate to share your unique background and perspectives. This can help you stand out in a competitive candidate pool and demonstrate that you would contribute positively to the company culture.

By following these tips, you can approach your interview with confidence and a clear strategy, increasing your chances of success at Oscar. Good luck!

In this section, we’ll review the various interview questions that might be asked during a Software Engineer interview at Oscar Insurance. The interview process will likely focus on your technical skills, problem-solving abilities, and cultural fit within the company. Be prepared to discuss your experience with software development, algorithms, system design, and your approach to collaboration and innovation.

Technical Skills

1. Can you explain the difference between a stack and a queue?

Understanding data structures is fundamental for software engineering roles. Be clear about their definitions and use cases.

How to Answer

Discuss the LIFO (Last In, First Out) nature of stacks and the FIFO (First In, First Out) nature of queues, along with examples of where each might be used in software applications.

Example

“A stack is a data structure that follows the Last In, First Out principle, meaning the last element added is the first to be removed. It’s commonly used in function call management. A queue, on the other hand, follows the First In, First Out principle, which is useful in scenarios like task scheduling where the first task added should be the first to be processed.”

2. Describe a time you optimized a piece of code. What was the problem, and what was your solution?

This question assesses your problem-solving skills and ability to improve existing systems.

How to Answer

Provide a specific example, detailing the initial performance issues, the steps you took to optimize the code, and the results of your changes.

Example

“I was working on a data processing pipeline that was taking too long to execute. I identified that a nested loop was causing inefficiencies. By refactoring the code to use a hash map for lookups instead of nested iterations, I reduced the processing time from several minutes to under 30 seconds.”

Algorithms and Problem Solving

3. Given a list of integers, write a function to find two numbers that add up to a specific target.

This is a common algorithm question that tests your coding skills.

How to Answer

Walk through your thought process, explaining how you would approach the problem before coding.

Example

“I would use a hash map to store the numbers I’ve seen so far. As I iterate through the list, I can check if the complement (target - current number) exists in the map. This allows me to find the solution in linear time.”

4. How would you implement a function to check if a string has balanced parentheses?

This question tests your understanding of algorithms and string manipulation.

How to Answer

Explain your approach using a stack data structure to keep track of opening parentheses.

Example

“I would use a stack to push every opening parenthesis and pop it when I encounter a closing parenthesis. If the stack is empty at the end, the parentheses are balanced; otherwise, they are not.”

System Design

5. How would you design a system to handle millions of claims per day?

This question assesses your system design skills and understanding of scalability.

How to Answer

Discuss the components of a scalable system, including load balancing, database sharding, and caching strategies.

Example

“I would design a microservices architecture where each service handles a specific aspect of the claims process. I would use load balancers to distribute incoming requests and implement a distributed database to handle the large volume of data. Caching frequently accessed data would also help reduce database load.”

6. Describe how you would approach migrating a legacy system to a new technology stack.

This question evaluates your experience with system migrations and change management.

How to Answer

Outline a step-by-step approach, including assessment, planning, execution, and testing.

Example

“I would start by assessing the current system to understand its architecture and dependencies. Then, I would create a detailed migration plan that includes timelines and resource allocation. During execution, I would implement the new stack in phases, ensuring thorough testing at each stage to minimize disruptions.”

Behavioral Questions

7. How do you handle conflicts within a team?

This question gauges your interpersonal skills and ability to work collaboratively.

How to Answer

Provide an example of a conflict you faced and how you resolved it through communication and compromise.

Example

“In a previous project, there was a disagreement about the direction of the implementation. I facilitated a meeting where each team member could express their views. By focusing on our common goals and finding a middle ground, we were able to agree on a solution that incorporated the best ideas from both sides.”

8. What motivates you to work in the healthcare technology space?

This question assesses your passion for the industry and alignment with the company’s mission.

How to Answer

Share your personal connection to healthcare or your desire to make a positive impact through technology.

Example

“I am motivated by the opportunity to improve people’s lives through technology. Working in healthcare allows me to contribute to solutions that can enhance patient care and streamline processes, making a real difference in the industry.”