Director, Product Design

Hi, we're Oscar. We're hiring a Director, Product Design to join our Product Design team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

We are seeking a strategic Product Design Director to lead a team of designers supporting our internal tools and enterprise ecosystem. In this role, you will oversee the designers building mission‑critical platforms that power our business operations. Your mission is to ensure our internal users receive the same high‑quality, user‑centric experiences as our external customers. As Director, you will uphold a rigorous quality bar, ensuring our tools are not only functional but empower employees to deliver exceptional value to the business and our end‑users.

You will report into the Sr. Director, Product Design.

This position is based in our Marina del Rey office, requiring a hybrid work schedule with 3 days of in‑office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule.

The base pay for this role is: $ - $ per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

• Partner with Product and Engineering leads to define area strategy, roadmaps, set measurable goals, and ensure the timely and efficient delivery of high-impact solutions.
• Connect the dots across multiple domains:
  Network Management, Provider Tooling, and Clinical Experiences, to ensure cohesive, end-to-end ecosystems.
• Propose and lead design-driven initiatives, facilitating discovery and framing long-term strategic opportunities that align with business goals.
• Lead and develop a high-performing team of seasoned designers, fostering a culture of continuous growth and creative excellence.
• Own team resourcing, performance management, and prioritization, optimizing workflows to ensure the team is focused on the highest-leverage work.
• Effectively represent the product design org in executive forums, articulating the rationale behind design directions and highlighting the impact on the business.
• Maintain an uncompromising standard for design execution and craft through direct feedback, design reviews, and hands‑on guidance.
• Manage stakeholder relationships, driving towards clarity around decision making and influencing direction through informed insights.
• Focus on scalability by implementing repeatable design processes and contributing to the evolution of a unified design language across multiple domains.
• Contribute to the future of the Product Design and Research function by optimizing our internal workflows, refining our engagement models, and ensuring the team has access to the best-in-class tooling and resources to do great work.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

• 10+ years of experience in product design, building and shipping applications or software across various experiences.
• 5+ years of experience in a design leadership role, directly contributing and leading people, process, and product strategies.
• Ability to solve difficult problems through past work experience and case studies with evidence of design contributions across power‑user interfaces.
• Experience shaping design direction and strategic thinking, identifying goals and opportunities, and making impact-based decisions.
• Engaging presentation skills and the ability to tell compelling stories to cross-functional audiences.
• Ability to analyze and deconstruct complex systems into smaller bits & pieces.
• Well-developed design and research skills, ability to give feedback and mentor designers in growing their technical skill-sets.

• Ability to solve difficult problems through past work experience and case studies.
• Ability to lead with empathy, transparency, and inclusivity, holding a high bar for accountability…