Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Oscar Health

Location: New York, New York, United States

Job Type: Full-Time

Category: Product Design / UX Design

Date Posted: 2026-09-14

Experience Level: Mid-Senior Level (4+ years)

Remote Status: Hybrid

🚀 Role Summary

• Lead the design process for mission-critical internal tools that support Oscar's insurance and care operations, focusing on complex workflows involving claims, risk adjustment, provider networks, and clinical care.

• Drive the definition and delivery of clear, effective, and user-centered experiences across a suite of operational tools, requiring strong systems thinking and comfort with ambiguity.

• Leverage AI-enabled design practices using tools like Claude and Codex for problem clarification, workflow exploration, risk identification, and rapid prototyping, while ensuring design-system alignment and production readiness in Figma.

• Collaborate deeply with product managers, engineers, researchers, data partners, clinicians, operational teams, and other designers to translate complex operational challenges into innovative and scalable design solutions.

📝 Enhancement Note: This role is specifically focused on "Internal Tools" design within the health insurance sector, emphasizing operational workflows and data-rich, technically complex environments. The integration of AI tools (Claude, Codex) into the design process is a significant differentiator and a core expectation for candidates.

📈 Primary Responsibilities

• Independently lead the end-to-end design process for intricate operational problems, balancing immediate delivery needs with a cohesive long-term product vision.

• Develop profound empathy and understanding for internal users, their daily goals, and the operational contexts in which they perform their duties.

• Act as a strategic partner to Product Management and Engineering, contributing to product direction, identifying key opportunities, establishing measurable success metrics, and influencing roadmap development.

• Systematically map complex workflows and interconnected systems to pinpoint inefficiencies, bottlenecks, redundancies, and opportunities for significant simplification and improvement.

• Drive design initiatives from initial discovery and conceptualization through detailed interaction design, seamless implementation, and continuous post-launch iteration.

• Employ a data-informed approach, utilizing research findings, analytics, hypotheses, and experimentation to validate design concepts and refine product direction.

• Create interactive prototypes to facilitate team understanding, test critical assumptions, and build confidence in proposed solutions before committing to full development.

• Facilitate impactful workshops, design sprints, and visioning sessions to foster cross-functional alignment and drive clarity on complex product challenges.

• Actively utilize AI tools (e.g., Claude, Codex) to clarify user and business needs, explore diverse solution paths, and identify potential requirements, risks, and edge cases early in the design cycle.

• Employ AI-assisted tools to rapidly build and test realistic interactions, end-to-end workflows, and front-end prototypes, accelerating the discovery and validation phases.

• Exercise strong design judgment to refine and elevate AI-generated output, ensuring optimal structure, behavior, accessibility, and overall visual quality.

• Collaborate closely with engineering partners to identify reusable prototypes, design patterns, or components that can be efficiently integrated into production code.

• Utilize Figma to ensure all validated concepts are fully documented with complete states, adhere to established design system patterns, and are production-ready.

• Document and disseminate effective prompts, workflows, prototypes, and lessons learned to enhance the AI proficiency of the broader design team.

• Ensure responsible and compliant use of AI tools, adhering to Oscar’s strict privacy, security, and member-data handling policies.

• Work hand-in-hand with engineers throughout the implementation phase to guarantee the shipped product meets the intended quality standards and user experience goals.

• Navigate and address technical constraints effectively without compromising user needs, product quality, or long-term system scalability.

• Contribute to the development and maintenance of a consistent, scalable, and integrated user experience across Oscar’s portfolio of internal products.

• Actively use and contribute to the enhancement of shared design system components, established patterns, and evolving standards.

• Apply Oscar’s brand guidelines, accessibility standards, and core design principles consistently across all product experiences.

• Present design work with clarity, articulate the rationale behind decisions, and proactively solicit constructive feedback at appropriate project stages.

• Participate actively in team critiques, contribute to the refinement of design practices, and support the professional growth of the wider Product Design organization.

• Ensure compliance with all applicable laws and regulations relevant to healthcare operations and data handling.

• Perform other duties as assigned to support team and company objectives.

📝 Enhancement Note: The responsibilities highlight a blend of strategic product thinking, deep operational workflow understanding, and hands-on design execution. The emphasis on AI tool integration, systems thinking, and cross-functional collaboration is central to this role.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience.

Experience:

• Minimum of 4 years of progressive experience in Product Design, UX Design, or a closely related discipline.

• Demonstrated experience (at least two distinct examples) in designing and successfully shipping complex web, mobile, SaaS, or internal-tool experiences.

• A minimum of 2 years of dedicated experience in owning and managing relationships with cross-functional stakeholders, ensuring alignment and effective communication. Required Skills:

• Product Thinking & Strategy: Ability to define product direction, identify opportunities, and contribute to roadmaps based on user needs and business goals.

• Systems Thinking: Proficiency in mapping complex workflows, understanding interdependencies, and designing cohesive experiences across multiple products or user segments.

• Interaction Design: Expertise in crafting intuitive and efficient user flows, defining states, and designing clear, functional interactions.

• Visual Design Craft: Strong aesthetic sensibility and ability to create polished, accessible, and brand-aligned visual interfaces.

• Prototyping: Proficiency in creating interactive prototypes (e.g., using Figma) to test concepts, validate assumptions, and communicate design solutions effectively.

• Figma Proficiency: Advanced skills in using Figma for design, prototyping, collaboration, and design system management.

• AI-Assisted Design Tools: Active and demonstrable experience using AI tools such as Claude, Codex, or comparable AI-assisted tools within a product design workflow for exploration, ideation, and prototyping.

• Cross-Functional Collaboration: Proven ability to work effectively with Product Managers, Engineers, Researchers, and other stakeholders.

• Stakeholder Management: Skill in building rapport, managing expectations, and communicating design decisions and rationale to diverse stakeholder groups.

• Workflow Mapping & Analysis: Ability to dissect and visualize complex operational processes to identify pain points and opportunities for improvement.

• Autonomy & Ambiguity: Demonstrated ability to work independently and drive projects forward in complex or ambiguous product areas.

• Data-Informed Design: Experience using research, data, and experimentation to inform design decisions and measure product impact.

• Communication Skills: Excellent written, visual, and verbal communication abilities, with a capacity to articulate design rationale clearly.

Preferred Skills:

• Experience designing SaaS products, enterprise software, CRM platforms, operational tools, or similarly complex applications.

• Experience within the healthcare, insurance, financial services, or another highly regulated industry.

• Expertise in designing data-dense interfaces, configurable workflows, permission systems, or multi-role environments.

• Proven track record of simplifying fragmented products, workflows, or complex product ecosystems.

• Experience contributing to or closely collaborating with a design system or front-end component library.

• Experience creating realistic or coded prototypes that closely simulate final product behavior.

• Familiarity with front-end development concepts, including components, states, responsive behavior, and accessibility best practices.

• Experience planning and conducting user research, including customer interviews and usability testing.

• Proficiency in using animated prototypes, working software demonstrations, or detailed user-flow diagrams to convey product vision.

• Experience contributing reusable prompts, patterns, components, or workflows to a broader team's toolkit.

• Experience designing AI-powered products, with an understanding of considerations like transparency, user control, trust, and uncertainty.

• A strong interest in accessibility, design ethics, and the specific responsibilities associated with designing healthcare products.

• A genuine, inquisitive, and collaborative working style characterized by humility, determination, and openness to feedback.

📝 Enhancement Note: The requirements emphasize a strong foundation in core product design principles, coupled with specific experience in complex operational environments and the emerging use of AI in design. The distinction between required and preferred skills clearly delineates essential qualifications from advantageous ones.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Product Thinking Case Studies: Showcase at least two comprehensive case studies detailing your involvement in designing and shipping complex web, mobile, SaaS, or internal tool experiences from problem definition to successful launch and iteration.

• Systems Thinking Demonstration: Include examples that clearly illustrate your ability to map complex workflows, understand system interdependencies, and design solutions that integrate seamlessly across multiple user touchpoints or product areas.

• Interaction & Visual Design Craft: Present detailed examples of your interaction design process, including user flows, wireframes, and prototypes, alongside polished visual designs that adhere to brand guidelines and accessibility standards.

• AI Integration Examples: Dedicate a section or specific case study to demonstrate how you've utilized AI tools (like Claude or Codex) in your design process, highlighting how these tools aided in problem clarification, workflow exploration, risk identification, or rapid prototyping, and how your own judgment shaped the final output.

• Cross-Functional Collaboration Evidence: Within your case studies, provide context on how you partnered with Product Managers, Engineers, and other stakeholders, illustrating communication strategies and alignment processes.

Process Documentation:

• Workflow Analysis & Optimization: Present documentation or case study elements that detail your process for mapping complex operational workflows, identifying pain points, and proposing data-driven solutions for simplification and efficiency.

• Design Process Methodology: Clearly outline your end-to-end design process, from discovery and research through ideation, prototyping, user testing, implementation support, and iteration, emphasizing how you adapt this process to different project needs and constraints.

• System Integration & Scalability: Demonstrate through your portfolio how you consider system integration, scalability, and adherence to design system standards when developing solutions, particularly for internal tools or complex platforms.

• Metrics & Impact Measurement: For each case study, clearly articulate the measurable outcomes and impact of your design solutions, referencing key performance indicators (KPIs) or metrics that demonstrate user adoption, efficiency gains, or other business value.

📝 Enhancement Note: The portfolio requirements are heavily geared towards demonstrating practical application of design skills in complex, operational contexts, with a strong emphasis on systems thinking and the innovative use of AI tools. Quantifiable impact and clear process documentation are crucial.

💵 Compensation & Benefits

Salary Range: $149,040.00 - $195,615.00 per year.

Benefits:

• Comprehensive Medical, Dental, and Vision insurance plans.

• Generous Unlimited Vacation program, encouraging work-life balance.

• Eligibility for Company Equity Grants, providing ownership in Oscar's growth.

• Annual Performance Bonuses, rewarding contributions and achievements.

• 11 Paid Holidays to observe national and company-recognized holidays.

• Paid Sick Time for personal health and recovery needs.

• Paid Parental Leave to support new parents.

• 401(k) plan participation for long-term financial planning.

• Life Insurance coverage to provide financial security for beneficiaries.

• Disability Insurance to offer income protection in case of extended illness or injury.

• Paid Wellness Time and Reimbursements to support employee well-being.

Working Hours: Standard full-time work hours are expected, typically around 40 hours per week. The hybrid work model offers flexibility in structuring the work week, with specific days designated for in-office collaboration.

📝 Enhancement Note: The salary range provided is competitive for a Senior Product Designer role in a high-cost-of-living area like New York City, especially within the tech and healthcare sectors. The benefits package is robust, offering a comprehensive suite of health, financial, and lifestyle support.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance / Health Technology. Oscar operates within the highly regulated and complex health insurance industry, leveraging technology to disrupt traditional models and improve member experience. This context means a focus on compliance, data security, and user empathy is paramount.

Company Size: Oscar Health is a growing, publicly traded company with a significant employee base (implied by the range of benefits and structured roles). This size suggests a balance between established processes and a dynamic, evolving environment, offering opportunities for impact and career progression.

Founded: Founded in 2012, Oscar has a history of innovation in the health insurance space, aiming to create a more member-centric and technology-driven approach. This founding ethos likely translates into a culture that values forward-thinking, problem-solving, and leveraging technology to achieve its mission.

Team Structure:

• Product Design Team: This role is part of the Product Design team, reporting to a Product Design Director. The team likely comprises various design specializations (UX, UI, Research, Content Design) working across different product areas.

• Internal Tools Focus: The specific team for this role focuses on "Internal Tools," meaning designers here support the operational backbone of Oscar, enabling clinical, core insurance, and network teams. This requires close collaboration with operational stakeholders.

• Cross-Functional Squads: Designers typically work within product squads, which are cross-functional teams comprising Product Managers, Engineers, Designers, and potentially Data Analysts or other specialists, fostering a collaborative and agile development environment.

Methodology:

• AI-Enabled Design Practice: Oscar is actively building an AI-enabled design practice, integrating tools like Claude and Codex into the design workflow for efficiency and enhanced exploration.

• Agile & Iterative Development: Given the tech-focused nature of Oscar and its likely use of modern development practices, an agile and iterative approach to product development is expected, with design playing a key role in continuous improvement.

• Data-Driven Decision Making: The company's reliance on a technology platform suggests a strong emphasis on data analysis to understand user behavior, operational efficiency, and product performance, which informs design decisions.

Company Website: https://hioscar.com/

📝 Enhancement Note: The company context highlights Oscar's position as a tech-forward disruptor in the health insurance industry. The emphasis on internal tools means the designer will be solving critical, often complex, operational challenges, requiring a deep understanding of business processes and user workflows. The integration of AI is a strategic initiative that candidates should be prepared to engage with.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a "Senior Product Designer." This level typically signifies an individual contributor with a high degree of autonomy, capable of independently managing complex projects, influencing product strategy, and mentoring junior designers. For an internal tools role, this means taking ownership of significant operational systems and workflows.

Reporting Structure: The Senior Product Designer reports to a Product Design Director. This provides a clear line of leadership and mentorship, with the director likely overseeing broader design strategy and team development. The role will also involve close daily collaboration within cross-functional product squads.

Operations Impact: The work on internal tools directly impacts Oscar's operational efficiency, the effectiveness of its care and insurance teams, and ultimately, the quality of service delivered to members. Successful design in this area can lead to significant cost savings, improved employee productivity, and enhanced member outcomes by streamlining critical business processes.

Growth Opportunities:

• Leadership in AI Design: As Oscar builds its AI-enabled design practice, this role offers a unique opportunity to become a leader in applying AI tools responsibly and effectively within product design, potentially shaping best practices for the company.

• Specialization in Operational Systems: Deepening expertise in designing complex operational workflows within the healthcare/insurance sector can lead to specialized career paths in enterprise software design, workflow optimization, or operational excellence.

• Mentorship & Team Contribution: Senior designers are expected to mentor junior team members, contribute to design critiques, and help evolve design processes and standards, offering opportunities to develop leadership and coaching skills.

• Broader Product Influence: Successful contributions to internal tools can lead to opportunities to influence broader product strategies across Oscar, potentially moving into product areas with more direct member interaction or taking on more strategic design leadership roles.

📝 Enhancement Note: This Senior role offers significant autonomy and the chance to shape critical internal systems. The growth path is strongly tied to developing expertise in complex operational design, AI integration, and potentially leading design initiatives within a growing, mission-driven company.

🌐 Work Environment

Office Type: The position is based in Oscar's New York City office, requiring a hybrid work schedule. This suggests a modern office environment designed to foster collaboration and innovation.

Office Location(s): New York City, New York, United States. Specific details about the office location and amenities would typically be available during the interview process or on the company's career page.

Workspace Context:

• Collaborative Hub: The hybrid model, with mandatory in-office days (including Thursdays for team meetings), indicates an emphasis on in-person collaboration, brainstorming, and team building.

• Technology-Rich Environment: As a tech-first company, expect access to modern design tools, high-performance workstations, and robust digital collaboration platforms.

• Cross-Functional Interaction: The workspace is designed to facilitate easy interaction with product managers, engineers, researchers, and other operational stakeholders, fostering a cohesive team dynamic.

Work Schedule: A hybrid work schedule is mandated, requiring 3 days per week in the New York City office, with Thursdays specifically designated for in-office team activities. This structure aims to balance the benefits of remote flexibility with the advantages of in-person collaboration.

📝 Enhancement Note: The hybrid nature