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 New York City 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. #LI-Hybrid

• →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 and outcomes.