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: March 05, 2026

Experience Level: 6+ Years

Remote Status: Hybrid

🚀 Role Summary

• Spearhead end-to-end product design initiatives, from ideation and discovery through to detailed specification and delivery, with a high degree of autonomy.

• Drive product strategy and solutions by developing deep expertise in user needs and the business domain, particularly within the complex healthcare insurance provider network ecosystem.

• Foster strong collaborative relationships with cross-functional teams, including Product Management, Engineering, Marketing, Brand Design, and User Research, to ensure cohesive product development.

• Play a significant role in defining team objectives and strategic direction, effectively bridging user needs with business requirements to achieve impactful outcomes.

• Manage and cultivate stakeholder relationships to drive clear decision-making processes and alignment across diverse teams.

📝 Enhancement Note: This role is positioned as a Senior Product Designer focusing on internal tools for provider network management within a health insurance technology company. The emphasis on "Network Pillar," "operational workflows," and "SaaS or internal tools" indicates a need for strong systems thinking and experience with complex, data-driven applications. The hybrid work model with specific office days suggests a preference for collaborative in-person interaction.

📈 Primary Responsibilities

• Own the complete product design lifecycle, from initial concept exploration and user research to the creation of high-quality design specifications, ensuring a balance between speed of execution and overall design polish, with minimal direct supervision.

• Cultivate a comprehensive understanding of the target users and the intricacies of the healthcare provider network domain to effectively inform product strategy and design solutions throughout the entire product development process.

• Collaborate effectively with a diverse group of internal partners, including fellow product designers, product managers, marketing specialists, brand designers, software engineers, and user researchers, to ensure seamless product integration and user experience.

• Contribute significantly to the definition of team goals, strategic initiatives, and OKRs, acting as a key connector between user needs, business objectives, and technical feasibility.

• Proactively manage and nurture relationships with various stakeholders, facilitating clear communication and driving consensus towards effective decision-making and project progression.

• Lead and facilitate workshops, vision-setting activities, and presentations to align teams, gather insights, and communicate design strategies and outcomes.

• Apply a high standard of visual and interaction design craft to elevate the quality of user experiences, setting new benchmarks for the team and contributing to the evolution of the company's design systems.

• Integrate the Oscar brand identity and principles seamlessly across all product experiences to maintain a consistent and recognizable brand presence.

• Ensure strict compliance with all applicable laws and regulations pertinent to the healthcare industry.

• Undertake additional duties as assigned to support team and organizational objectives.

📝 Enhancement Note: The responsibilities highlight a need for a designer who can operate independently, manage complex projects, and influence product strategy. The emphasis on "end-to-end design process," "minimal oversight," and "defining team goals" suggests a leadership component within the design function for this role.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field is often preferred for Senior Product Designer roles. Equivalent practical experience will also be considered.

Experience: Minimum of 6 years of progressive experience in Product Design, UX Design, or a closely related field, with a proven track record of designing and shipping complex digital interfaces. A minimum of 3 years of direct experience in managing and influencing stakeholders is required.

Required Skills:

• End-to-End Design Ownership: Demonstrated ability to manage the entire design process from discovery, user research, and ideation through to detailed interaction design, visual design, and specification for engineering handoff, with minimal supervision.

• Complex Interface Design: Concrete examples and a robust portfolio showcasing the successful design and launch of intricate, user-friendly interfaces for web, mobile, or internal tools.

• Stakeholder Management: Proven experience in effectively managing relationships, communicating design decisions, and driving alignment with product managers, engineers, business leaders, and other key stakeholders.

• Systems Thinking: Ability to understand and design for complex systems, including interconnected workflows, data models, and user journeys within a large organization.

• Collaboration & Communication: Excellent verbal and written communication skills, with the ability to articulate design rationale, lead workshops, and present effectively to diverse audiences.

• Visual & Interaction Design Craft: Strong proficiency in creating polished, intuitive, and aesthetically pleasing user interfaces and interaction patterns.

Preferred Skills:

• Healthcare Industry Experience: Familiarity with the nuances, regulations, and user needs within the healthcare sector.

• SaaS or Internal Tool Design: Prior experience designing sophisticated software-as-a-service (SaaS) platforms or internal business tools.

• Design Systems Expertise: Experience in contributing to, or leveraging, established design systems to ensure consistency and efficiency.

• Prototyping & User Research: Proficiency in using advanced prototyping tools and methodologies, and experience conducting user research to validate design decisions.

• Storytelling: Ability to communicate design concepts effectively through methods like animated prototypes, user flow diagrams, and compelling presentations.

• Accessibility & Design Ethics: A strong understanding and interest in design ethics, accessibility standards, and their application in the healthcare context.

• Mentorship & Coaching: Experience in guiding and elevating junior designers through thoughtful coaching and collaborative practices.

📝 Enhancement Note: The requirements emphasize a senior-level designer capable of independent work, strategic influence, and managing complex stakeholder dynamics. The "Bonus points" suggest that experience in healthcare, internal tools, and advanced design skills like prototyping and storytelling will be highly valued.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Case Studies: Showcase 2-3 comprehensive case studies detailing your involvement from initial problem definition and discovery through to final shipped product. Each case study should clearly articulate the problem, your design process, key decisions, and the measurable impact.

• Complex Problem Solving: Include examples that demonstrate your ability to tackle complex user problems and translate them into intuitive and effective design solutions, particularly for internal tools or SaaS platforms.

• Systems Design Thinking: Present work that illustrates your capacity for systems thinking, showing how you've designed for interconnected workflows, data management, or scalable user experiences within a larger product ecosystem.

• Stakeholder Collaboration: Evidence of how you've managed stakeholder relationships, incorporated feedback, and navigated trade-offs to achieve successful design outcomes.

• Visual & Interaction Craft: High-quality visual mockups and interactive prototypes that exemplify your design sensibilities and attention to detail.

Process Documentation:

• Discovery & Research: Detail your approach to understanding user needs, business requirements, and technical constraints, including methodologies used (e.g., user interviews, competitive analysis, heuristic evaluations).

• Design Iteration & Validation: Explain how you iterate on designs based on feedback and testing, including the use of prototyping, user testing, and A/B testing where applicable.

• Cross-Functional Collaboration: Describe your process for working with product managers, engineers, and other teams, including how you hand off designs and ensure implementation quality.

• Metrics & Impact: Articulate how you measure the success of your designs, focusing on key performance indicators (KPIs) related to user satisfaction, operational efficiency, or business goals.

📝 Enhancement Note: For a senior role, the portfolio must go beyond just showcasing polished UI. It needs to demonstrate strategic thinking, process maturity, and the ability to deliver tangible business value, especially in the context of internal tools and complex systems.

💵 Compensation & Benefits

Salary Range: $149,040.00 - $195,615.00 per year. This range reflects a Senior Product Designer role in New York City, considering the specified experience level and the competitive nature of the tech and healthcare industries.

Benefits:

• Medical, Dental, and Vision Insurance: Comprehensive health coverage for employees and their families.

• Unlimited Vacation Program: Flexibility and trust in managing personal time off.

• Company Equity Grants: Opportunity to share in the company's growth and success.

• Annual Performance Bonuses: Potential for additional compensation based on individual and company performance.

• 11 Paid Holidays: Designated days off for national holidays.

• Paid Sick Time: Time off for personal illness or medical appointments.

• Paid Parental Leave: Support for new parents during a significant life event.

• 401(k) Plan Participation: Retirement savings plan with potential company matching.

• Life Insurance: Financial protection for beneficiaries.

• Disability Insurance: Income replacement in case of short-term or long-term disability.

• Paid Wellness Time: Dedicated time for personal well-being activities.

• Wellness Reimbursements: Financial support for wellness-related expenses.

Working Hours: The standard working hours are 40 hours per week. The role is hybrid, requiring 3 days in the New York City office per week, with Thursdays designated as a mandatory in-office day for team meetings and events.

📝 Enhancement Note: The provided salary range is within industry standards for a Senior Product Designer in a major metropolitan area like New York City. The benefits package is robust, offering a mix of traditional health and retirement benefits along with incentives like equity and bonuses, and a flexible vacation policy.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance & Technology. Oscar Health operates at the intersection of healthcare and technology, aiming to disrupt the traditional health insurance market with a tech-driven, member-centric approach. This context means designers will work within a highly regulated industry but with a startup's agility and innovation focus.

Company Size: Oscar Health is a significant player in the insurtech space, likely falling into the "Large" to "Very Large" category based on typical tech company growth. This implies a structured environment with established processes but also opportunities for impact across various departments.

Founded: Oscar Health was founded in 2012. This indicates a company that has moved beyond its early startup phase and is now a mature, scaling organization with established product lines and operational frameworks.

Team Structure:

• Product Design Team: The designer will report into the Senior Director, Product Design, indicating a hierarchical structure within the design department. The role is part of the "Network Pillar," suggesting a specialized focus within the broader product organization.

• Cross-Functional Collaboration: The role emphasizes close partnership with Product Managers, Engineers, Marketers, Brand Designers, and Researchers, highlighting a matrixed and collaborative approach to product development.

• Operational Integration: A key aspect of this role is working with "operational stakeholders," meaning the design will directly impact internal teams responsible for managing the provider network.

Methodology:

• Agile Development: Given the tech industry context, it's highly probable that Oscar Health utilizes agile or lean methodologies for product development, emphasizing iterative design and rapid deployment.

• Data-Driven Decision Making: The company's focus on a "full stack technology platform" suggests a strong reliance on data analytics to inform product strategy, user understanding, and performance measurement.

• User-Centric Design: The mission to be a "health insurance company we would want for ourselves" underscores a commitment to user empathy and designing experiences that prioritize member and provider needs.

Company Website: http://www.hioscar.com/careers

📝 Enhancement Note: Oscar Health's positioning as an innovative health insurance provider with a strong technology backbone means this role offers the chance to work on impactful products within a regulated but rapidly evolving industry. The "Network Pillar" focus is critical for understanding the specific domain expertise required.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as a "Senior Product Designer." This level typically signifies a designer who can independently own significant product areas, mentor junior team members, and influence product strategy. It's a critical individual contributor role with expectations of leadership in design thinking and execution.

Reporting Structure: The Senior Product Designer will report to the Senior Director, Product Design. This indicates a clear line of reporting within the design department, with opportunities for mentorship from a senior leader. The role also involves extensive collaboration with Product Managers and Engineers on the "Network Pillar" team.

Operations Impact: The role's direct impact is on designing and shipping tools that power Oscar's provider network evaluation, management, and configuration. This means the designer will be instrumental in improving operational workflows, enabling internal teams to make better decisions regarding network adequacy and provider relationships, and ultimately contributing to the quality, accessibility, and cost-effectiveness of healthcare services offered to members.

Growth Opportunities:

• Leadership in Design: Potential to grow into a Lead Product Designer or Design Manager role, taking on more strategic oversight and team leadership responsibilities within specialized product areas like the Network Pillar.

• Domain Expertise: Deepen expertise within the complex healthcare and provider network domain, becoming a go-to subject matter expert for product and design challenges in this area.

• Cross-Functional Influence: Expand influence across different product pillars and departments by successfully delivering impactful design solutions for critical internal tools.

• Mentorship: Opportunity to formally or informally mentor junior designers, contributing to the growth of the broader design team and developing leadership skills.

• Strategic Contribution: Play a more significant role in shaping product strategy, OKRs, and long-term vision for the Network Pillar and beyond.

📝 Enhancement Note: The Senior designation implies a clear path for career progression within Oscar Health, either through specialization, leadership, or broader strategic influence, particularly within the critical provider network domain.

🌐 Work Environment

Office Type: Oscar Health operates with a hybrid work model, requiring 3 days per week in their New York City office. This suggests a modern office environment designed to facilitate collaboration, team meetings, and in-person brainstorming sessions.

Office Location(s): The position is based in the New York City office. Specific details about the office amenities or address would typically be provided during the interview process.

Workspace Context:

• Collaborative Spaces: The hybrid model indicates an office setup that likely includes meeting rooms, common areas, and potentially dedicated collaborative zones to support team interactions.

• Technology & Tools: As a tech-forward company, expect access to modern design software, collaboration platforms, and potentially specialized tools for managing complex data and workflows related to the provider network.

• Team Interaction: The required in-office days, especially Thursdays for team meetings, are designed to foster cohesion, spontaneous problem-solving, and a shared team culture.

Work Schedule: The role is full-time, with standard working hours of approximately 40 hours per week. The hybrid arrangement offers flexibility in choosing office days, balancing in-person collaboration with remote work flexibility.

📝 Enhancement Note: The hybrid nature of the role suggests a balance between focused individual work (potentially remote) and collaborative team engagement (in-office), typical of modern tech companies.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will likely review your application and portfolio to assess alignment with the core requirements. Be prepared to articulate your most relevant experience quickly.

• Portfolio Review & Design Challenge: Expect a session where you present your portfolio, focusing on 1-2 key case studies that demonstrate your ability to handle complex problems, systems thinking, and stakeholder management. A design challenge or exercise, either take-home or live, may be part of this stage to assess your problem-solving approach and design craft.

• Cross-Functional Interviews: Interviews with Product Managers, Engineers, and potentially other Designers from the "Network Pillar" team. These will focus on collaboration, technical understanding, and how you approach design within a team context.

• Leadership/Director Interview: A final interview with the Senior Director, Product Design, and potentially other senior leaders. This will assess your strategic thinking, leadership potential, cultural fit, and overall impact.

Portfolio Review Tips:

• Focus on Impact: For each case study, clearly articulate the problem, your specific role and process, the design decisions made, and most importantly, the measurable outcomes or impact on users and the business. Use metrics where possible.

• Show, Don't Just Tell: Use visuals, prototypes, and clear explanations to guide the reviewer through your thought process. Highlight how you navigated challenges and trade-offs.

• Tailor to the Role: Emphasize projects that showcase experience with internal tools, complex systems, or the healthcare domain, if applicable. Highlight your stakeholder management skills.

• Be Ready to Discuss: Prepare to answer detailed questions about your design choices, your process, and how you would approach scenarios relevant to Oscar Health's provider network challenges.

Challenge Preparation:

• Understand the Domain: Research Oscar Health, their mission, and the challenges of managing a provider network in health insurance.

• Systems Thinking Practice: Practice breaking down complex problems into smaller, manageable parts and thinking about interconnectedness.

• Communication Clarity: Be prepared to articulate your thought process clearly and concisely, especially when presenting design solutions or strategies.

• Focus on User & Business: Ensure your solutions address both user needs and business objectives, demonstrating an understanding of how design drives value.

📝 Enhancement Note: The interview process will likely be rigorous, focusing on a blend of design skill, strategic thinking, collaboration, and domain understanding. A well-curated portfolio that tells a compelling story of impact is crucial.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping Software: Proficiency with industry-standard tools such as Figma (highly probable given its prevalence), Sketch, Adobe Creative Suite (Illustrator, Photoshop).

• Prototyping Tools: Experience with tools like InVision, Principle, or Figma's built-in prototyping capabilities for creating interactive user flows and mockups.

• Collaboration Platforms: Familiarity with tools like Slack, Microsoft Teams, or Google Workspace for team communication and collaboration.

• Project Management Tools: Experience with tools like Jira, Asana, or Trello for managing design tasks and tracking project progress.

Analytics & Reporting:

• Analytics Platforms: While not a direct responsibility, understanding how to interpret data from platforms like Google Analytics, Amplitude, or Mixpanel is beneficial for informing design decisions.

• Data Visualization Tools: Familiarity with tools that help visualize data and user behavior, which might be used by product managers or data analysts, can aid collaboration.

CRM & Automation:

• CRM Systems: While this role is not directly in Sales Ops, understanding CRM principles (e.g., Salesforce) might be helpful if the internal tools interact with sales or provider relationship management data.

• Workflow Automation: Awareness of how automation impacts user workflows and operational efficiency is valuable, even if not directly building automation tools.

📝 Enhancement Note: The emphasis on internal tools and complex systems suggests a need for proficiency in modern design tools like Figma, which excel at collaborative design and component-based systems. Understanding how design integrates with broader business systems is also key.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A commitment to understanding and prioritizing the needs of both internal users (e.g., network managers) and external users (e.g., members, providers) to create empathetic and effective solutions.

• Collaboration & Transparency: Fostering an environment where ideas are shared openly, feedback is constructive, and cross-functional teams work together seamlessly towards common goals.

• Data-Driven Innovation: Leveraging data and insights to inform design decisions, measure impact, and drive continuous improvement in product and operational efficiency.

• Execution & Speed: Balancing thorough design processes with the need for rapid iteration and timely delivery in a fast-paced industry.

• Quality & Craftsmanship: Upholding high standards for design execution, from visual polish to interaction clarity, ensuring a professional and intuitive user experience.

Collaboration Style:

• Cross-Functional Integration: The design team actively partners with Product Management and Engineering from early discovery through to launch, ensuring alignment and shared ownership.

• Iterative Feedback Loops: A culture of regular feedback exchange through design reviews, sprint demos, and informal check-ins to refine designs and identify potential issues early.

• Knowledge Sharing: Encouraging designers to share best practices, learnings, and design patterns, contributing to the collective growth and consistency of the design team and its systems.

📝 Enhancement Note: The company culture likely emphasizes innovation, collaboration, and a strong focus on improving healthcare through technology, aligning with the values of a mission-driven organization.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Complexity: Designing for the intricate regulations, workflows, and data requirements of the healthcare provider network can be challenging. Balancing these complexities with user needs and a seamless experience requires strong problem-solving skills.

• Balancing Speed and Quality: The need to ship quickly in a fast-paced tech environment while maintaining high design standards and ensuring robust solutions for critical internal operations.

• Stakeholder Alignment: Managing diverse stakeholder perspectives and priorities to achieve consensus on design direction for complex internal tools.

• Evolving Healthcare Landscape: Adapting designs to changes in healthcare policy, market dynamics, and technological advancements within the industry.

Learning & Development Opportunities:

• Deepen Healthcare Domain Knowledge: Gain specialized expertise in health insurance operations, provider network management, and related regulatory frameworks.

• Lead Design Initiatives: Take on more ownership of strategic product areas, influencing roadmaps and driving design vision for critical internal tools.

• Mentorship and Coaching: Develop leadership skills by mentoring junior designers and contributing to the growth of the design team's capabilities.

• Advanced Design Techniques: Explore and implement advanced design methodologies, such as complex systems design, behavioral economics in UX, or advanced prototyping.

📝 Enhancement Note: The role presents significant opportunities for professional growth by tackling challenging problems in a critical industry, with a clear path for advancing within the design organization and developing specialized expertise.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design a complex internal tool. What were the biggest challenges, and how did you overcome them?" (Focus on process, user research, stakeholder management, and outcomes)

• "How do you balance the needs of multiple stakeholders with potentially conflicting priorities when designing a product?" (Highlight your communication, negotiation, and decision-making process)

Company & Culture Questions:

• "What interests you about Oscar Health and our mission to change healthcare?" (Research their mission, values, and recent news)

• "How do you see your role contributing to the success of the Network Pillar and Oscar's overall business objectives?" (Connect your skills to their specific goals)

Portfolio Presentation Strategy:

• Structure: Begin with a high-level overview of the project and its business/user impact. Then, dive into your specific role, the problem, your process (discovery, ideation, iteration, validation), key design decisions, and finally, the results/outcomes.

• Metrics & Impact: Quantify your achievements whenever possible. Use data to demonstrate the value of your design solutions (e.g., "reduced process time by X%", "increased user adoption by Y%", "improved data accuracy leading to Z savings").

• Visual Storytelling: Use clear visuals, wireframes, mockups, and prototypes to illustrate your design journey. Explain why you made certain design choices.

• Conciseness: Be mindful of time. Focus on the most impactful aspects of your projects and be prepared to answer questions for deeper dives.

📝 Enhancement Note: Preparation should focus on demonstrating strategic thinking, process maturity, and the ability to articulate impact, rather than just showcasing UI skills. Understanding Oscar Health's business and mission will be key.

📌 Application Steps

To apply for this operations position:

• Submit your application through the Oscar Health careers portal via the provided URL.

• Portfolio Customization: Curate your portfolio to prominently feature 2-3 case studies that best align with the requirements of designing complex interfaces, internal tools, or SaaS products. Highlight projects demonstrating systems thinking and stakeholder management.

• Resume Optimization: Tailor your resume to emphasize your 6+ years of Product/UX Design experience, explicitly mentioning your 3+ years in stakeholder management and any experience with complex interfaces or internal tools. Use keywords from the job description.

• Interview Preparation: Practice articulating your design process, decision-making rationale, and the impact of your work. Prepare to discuss your experience with hybrid work and your interest in the healthcare industry. Rehearse presenting your portfolio case studies.

• Company Research: Thoroughly research Oscar Health's mission, values, product offerings, and recent news. Understand their approach to technology and healthcare to better articulate your fit and interest during interviews.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

---