Preparing for an interview at Oscar Health requires a balanced approach that combines deep operational knowledge with strong interpersonal skills. You should focus your preparation on demonstrating how your past experiences align with the company's mission to revolutionize health insurance.

Role-Related Knowledge – You must demonstrate a deep understanding of project management methodologies, workflow optimization, and operational frameworks. Be prepared to discuss how you manage project lifecycles, mitigate risks, and use tools to track progress. Having a solid grasp of healthcare operations, insurance processes, or clinical programs will significantly strengthen your candidacy.

Problem-Solving Ability – Interviewers will evaluate how you approach complex, ambiguous challenges. You should practice structuring your thoughts logically, breaking down large problems into manageable components, and explaining your decision-making process. Focus on showing how you use data and metrics to guide your project strategy and measure success.

Stakeholder Alignment – Because this role requires constant collaboration across diverse departments, you must show that you can build strong relationships, influence without authority, and align teams with competing priorities. Be ready with examples of how you have successfully navigated matrixed organizations and facilitated clear, proactive communication.

Adaptability & Resilience – Oscar Health operates in a dynamic, highly regulated industry. Interviewers want to see that you can remain calm under pressure, adapt to changing priorities, and successfully guide your team through organizational transitions or unexpected project shifts.

The interview process for a Project Manager at Oscar Health is designed to evaluate both your technical execution capabilities and your alignment with the company's collaborative culture. The process typically moves from initial screens to a comprehensive panel round, though candidates should be prepared for a rigorous evaluation at every stage.

The journey begins with a standard recruiter screen to assess your background and high-level fit. This is followed by a hiring manager interview, which dives deeper into your specific project management experience and your understanding of the role's scope. If you pass this stage, you will move to the panel round. The panel is highly structured and often includes multiple consecutive sessions with senior managers, cross-functional partners, and sometimes senior leadership. A core component of this final stage is a Case Study, which you will receive in advance to prepare and submit before your panel presentations.

The timeline above outlines the typical progression from application to offer. Candidates should interpret this as a general framework, keeping in mind that the panel and case study stages require the most intensive preparation. Use this timeline to pace your study plan, ensuring you allocate sufficient time to draft and refine your case study presentation before the final loop.

To stand out during your Oscar Health interviews, you must understand the specific competencies the hiring team evaluates during each interaction.

Case Study & Problem Solving

The case study is a pivotal element of the panel interview. It is designed to simulate a real-world operational challenge you would face as a Project Manager at Oscar Health. You will be asked to analyze a scenario, identify bottlenecks, propose a structured solution, and define success metrics.

Be ready to go over:

• Structured Frameworks – How you organize your approach to an ambiguous operational problem.
• Resource Allocation – How you determine the staffing, technology, and budget required to execute your proposed solution.
• Risk Mitigation – Identifying potential failure points in your plan and outlining proactive steps to prevent them.
• Advanced concepts – Operational capacity planning, cost-benefit analysis of workflow automation, and scaling pilot programs to enterprise-wide initiatives.

Example scenarios:

• "You are tasked with reducing the onboarding time for new clinical staff in the Case Management department by 20%. Walk us through your project plan."
• "A new state regulation requires a change to our member communication flow within 30 days. How do you manage this urgent implementation across product, legal, and operations?"

Stakeholder Management & Alignment

As a cross-functional leader, your ability to communicate effectively with diverse teams—ranging from software engineers to clinical directors—is paramount. Interviewers will closely observe how you build trust, manage expectations, and resolve conflicts.

Be ready to go over:

• Influence Without Authority – Strategies for motivating team members who do not report directly to you.
• Tailored Communication – Adjusting your communication style when presenting to executive leadership versus technical implementation teams.
• Conflict Resolution – Navigating disagreements regarding project scope, timelines, or resource allocation.
• Advanced concepts – Managing distracted or disengaged stakeholders, driving consensus across highly matrixed organizational structures, and managing change resistance during large-scale operational shifts.

Example scenarios:

• "Describe a time when a key stakeholder disagreed with your project direction. How did you handle the conflict and reach an agreement?"
• "How do you keep a highly distracted cross-functional team focused and engaged during a critical project phase?"

Operational Execution & Delivery

This area focuses on your ability to get things done. Oscar Health values execution-oriented professionals who can take a project from concept to completion while maintaining high standards of quality and efficiency.

Be ready to go over:

• Project Tracking & Tools – Your proficiency in using project management tools to monitor timelines, dependencies, and milestones.
• Agile vs. Waterfall – Knowing when to apply different methodologies based on the project's unique constraints and goals.
• Process Optimization – Identifying inefficiencies in existing workflows and implementing continuous improvement strategies.
• Advanced concepts – Managing critical path dependencies in multi-threaded programs, standardizing operational playbooks, and handling post-launch optimization phases.

Example scenarios:

• "Tell me about a project you managed that was failing. What indicators did you use to identify the failure, and how did you pivot to deliver a successful outcome?"
• "How do you ensure project documentation remains accurate and accessible to all team members throughout the project lifecycle?"