Oscar Insurance Product Manager Interview Questions + Guide in 2025

Oscar Insurance is an innovative health insurance company focused on leveraging technology to provide exceptional service to its members.

As a Product Manager at Oscar, you will play a pivotal role in shaping the future of healthcare solutions through cutting-edge technology. Your responsibilities will include defining and executing product strategies that drive AI investments, collaborating with engineers and data scientists to develop user-centric applications, and establishing measurable outcomes to gauge the success of your initiatives. A key aspect of your role will involve problem-solving across teams, ensuring that complex projects are delivered on time and meet the high standards set by stakeholders. To excel in this position, you should have a deep understanding of product management principles, experience with SQL and tech infrastructure, and the ability to effectively communicate insights derived from user research and data analysis.

Your work will be driven by Oscar's commitment to improving healthcare, making it crucial that candidates align with the company's values of innovation, collaboration, and a member-first approach. This guide will help you prepare for your interview by providing insights into the expectations for the role, common interview questions, and strategies for showcasing your skills and experiences effectively.

The interview process for a Product Manager at Oscar Insurance is structured and involves multiple stages designed to assess both technical and interpersonal skills. Here’s a breakdown of what you can expect:

1. Initial Screening

The process typically begins with a phone screening conducted by a recruiter. This initial conversation lasts about 30 minutes and focuses on your background, experience, and motivation for applying to Oscar. Expect standard questions about your understanding of the company and its mission, as well as your interest in the role.

2. Technical Phone Interview

Following the initial screening, candidates usually participate in a technical phone interview. This round is more in-depth and may include case study questions relevant to the role. You might be asked to solve problems related to product management, operational efficiency, or user experience. This stage is crucial for demonstrating your analytical skills and ability to think critically about product challenges.

3. Onsite Interviews

The onsite interview is a comprehensive assessment that typically includes multiple rounds with various stakeholders. You can expect to meet with senior product managers, engineers, and possibly members from the operations team. This stage often includes a mix of behavioral interviews, case studies, and technical assessments. You may be asked to present a case study or a project you’ve worked on, showcasing your problem-solving abilities and how you approach product management challenges.

4. Final Round

In the final round, candidates may have a series of one-on-one interviews with senior leadership or cross-functional team members. This is an opportunity to discuss your vision for the product, how you would define success metrics, and how you would collaborate with different teams. Expect to articulate your thought process clearly and demonstrate your ability to influence without direct authority.

Throughout the interview process, be prepared to discuss your past experiences in product management, your approach to prioritization, and how you handle complex projects.

As you prepare for your interview, consider the types of questions that may arise, particularly those that assess your understanding of product metrics, user needs, and operational challenges.

In this section, we’ll review the various interview questions that might be asked during a Product Manager interview at Oscar Insurance. The interview process will likely focus on your ability to define product strategy, collaborate with cross-functional teams, and solve complex problems within the healthcare technology space. Be prepared to discuss your past experiences, your understanding of product management principles, and your approach to data-driven decision-making.

Experience and Background

1. Can you describe a product you managed from conception to launch? What were the key challenges you faced?

This question assesses your experience in product management and your ability to navigate challenges.

How to Answer

Discuss a specific product, focusing on your role, the challenges encountered, and how you overcame them. Highlight your problem-solving skills and the impact of your decisions.

Example

“I managed the launch of a telehealth platform aimed at improving patient access to care. One key challenge was integrating the platform with existing healthcare systems. I coordinated with engineers and stakeholders to ensure seamless integration, which ultimately led to a 30% increase in patient engagement.”

2. How do you prioritize features in your product roadmap?

This question evaluates your prioritization skills and understanding of product management frameworks.

How to Answer

Explain your approach to prioritization, including any frameworks you use (e.g., RICE, MoSCoW). Discuss how you balance stakeholder needs with user feedback and business goals.

Example

“I use the RICE framework to prioritize features based on reach, impact, confidence, and effort. For instance, when prioritizing features for our claims processing tool, I gathered user feedback and aligned it with our business objectives, ensuring we focused on high-impact features that would enhance user experience.”

Technical Skills

3. What is your experience with SQL and data analysis? Can you provide an example of how you used data to inform a product decision?

This question assesses your technical skills and ability to leverage data in product management.

How to Answer

Discuss your experience with SQL and data analysis, providing a specific example where data influenced your product decisions.

Example

“I have used SQL extensively to analyze user behavior data. For example, I discovered that users were dropping off during the onboarding process. By analyzing the data, I identified specific pain points and collaborated with the design team to streamline the onboarding experience, resulting in a 20% increase in user retention.”

4. Describe a time when you had to work with engineers and designers to solve a complex problem. What was your approach?

This question evaluates your collaboration skills and ability to work cross-functionally.

How to Answer

Share a specific example that highlights your collaborative approach, communication skills, and problem-solving abilities.

Example

“When we faced issues with our mobile app’s performance, I organized a series of workshops with engineers and designers to identify the root cause. By facilitating open communication and brainstorming sessions, we developed a solution that improved app speed by 40%.”

Behavioral Questions

5. Tell me about a time you received critical feedback. How did you handle it?

This question assesses your ability to accept feedback and grow from it.

How to Answer

Discuss a specific instance where you received constructive criticism, how you responded, and what you learned from the experience.

Example

“I once received feedback that my project updates were too technical for non-technical stakeholders. I took this to heart and worked on simplifying my communication. I now focus on presenting key insights and impacts rather than technical details, which has improved stakeholder engagement.”

6. How do you handle conflicts within a team? Can you provide an example?

This question evaluates your conflict resolution skills and ability to maintain team dynamics.

How to Answer

Share a specific example of a conflict you encountered, how you addressed it, and the outcome.

Example

“In a previous project, there was a disagreement between the design and engineering teams regarding feature implementation. I facilitated a meeting where both sides could express their concerns. By encouraging open dialogue, we reached a compromise that satisfied both teams and kept the project on track.”

Case Study Questions

7. Imagine you are tasked with improving the user experience of our health insurance application. What steps would you take?

This question assesses your problem-solving skills and understanding of user experience.

How to Answer

Outline a structured approach to improving user experience, including user research, data analysis, and collaboration with design and engineering teams.

Example

“I would start by conducting user interviews to gather feedback on pain points. Next, I would analyze usage data to identify trends. Based on these insights, I would collaborate with the design team to prototype solutions and conduct usability testing before implementing changes.”

8. How would you approach defining OKRs for a new AI-driven product?

This question evaluates your understanding of goal-setting and product strategy.

How to Answer

Discuss your approach to defining Objectives and Key Results (OKRs), emphasizing alignment with business goals and measurable outcomes.

Example

“I would begin by aligning with stakeholders to understand the strategic goals for the AI product. Then, I would define clear objectives, such as improving user engagement or reducing operational costs, and establish measurable key results, like achieving a 25% increase in user interactions within six months.”