As a UX/UI Designer at Oscar Health, your day-to-day work will be highly collaborative and fast-paced. You will be embedded within a cross-functional product squad, working alongside product managers, engineers, data analysts, and domain experts (such as clinical directors or insurance operations leads).

Your primary responsibility will be to own the end-to-end design process for your product area. This includes conducting generative user research, mapping user flows, wireframing, prototyping, and delivering high-fidelity UI designs. You will also participate in regular design critiques, giving and receiving feedback to maintain a high bar of quality across the entire design organization.

To be competitive for a UX/UI Designer position, you must demonstrate a strong balance of core design skills and collaborative soft skills.

• Must-have skills:

  • A strong portfolio showcasing shipped digital products, with a focus on web and mobile interfaces.
  • Mastery of modern design tools, specifically Figma, including advanced prototyping and component libraries.
  • Demonstrated ability to simplify complex, data-heavy workflows into intuitive user interfaces.
  • Excellent communication skills, with the ability to articulate design decisions to non-design stakeholders.

• Nice-to-have skills:

  • Experience designing in highly regulated industries, such as healthcare, fintech, or insurance.
  • Basic understanding of front-end development (HTML/CSS/JS) to facilitate smoother engineering handoffs.
  • Experience working with or contributing to enterprise-level design systems.

Q: How technical do I need to be? Do UX/UI Designers actually code at Oscar? A: While you are not expected to write production code daily, recruiters and designers emphasize that having a strong mental model of how front-end code works is highly beneficial. Knowing how your UI translates to CSS and React components will make you a much stronger candidate and partner to engineering.

Q: How does the team view candidates transitioning from design agencies? A: Candidates from agencies are welcome, but you must actively combat the bias that agency designers only focus on high-level visuals. In your portfolio walkthrough, emphasize long-term product thinking, how you scoped project timelines, and how you collaborated with developers beyond handoff.

Q: What is the company culture like for the design team? A: The design team is highly collaborative, mission-driven, and supportive. However, the broader company operates with a fast-paced, startup-like energy. Successful designers are those who are proactive, comfortable with ambiguity, and eager to take end-to-end ownership of their product space.

Q: How long does the hiring process typically take? A: The process generally takes between three to five weeks from the initial recruiter screen to the final decision. However, candidates should be prepared for potential scheduling delays and should stay in close contact with their recruiter.

To maximize your chances of success, keep these practical tips in mind as you prepare for your interviews at Oscar Health.

• Perfect your "Why Oscar" story: Healthcare is personal. Be prepared to talk about a personal experience or a systemic issue in healthcare that motivates you to work at a company trying to fix it.
• Showcase complex systems, not just clean UI: While beautiful visual design is essential, ensure your portfolio highlights how you solved a deeply complex user flow or data visualization problem.
• Address the agency-to-product transition proactively: If your resume consists primarily of agency work, explicitly state how you managed project constraints, worked with engineering, and measured post-launch success.

• Prepare for highly interactive sessions: Be ready to actively defend your design choices during the portfolio review. Treat the session as a collaborative workshop rather than a static presentation.

A UX/UI Designer role at Oscar Health offers a rare opportunity to apply your design craft to a mission that directly improves people's lives. By designing intuitive, clear, and empathetic digital experiences, you will help members navigate some of their most stressful healthcare moments with confidence.

To succeed in the interview process, focus on showcasing a portfolio that balances meticulous visual execution with deep, systems-level product thinking. Be prepared to demonstrate your technical literacy, your ability to collaborate across functional boundaries, and your genuine passion for solving complex healthcare challenges.

The salary data above represents the typical compensation structure for design roles at this level. When evaluating an offer, consider the entire package, including base salary, equity, and healthcare benefits—which are particularly robust given the company's core mission. For more detailed insights, interview reviews, and preparation resources, explore the community-contributed data on Dataford. Good luck with your preparation!