Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Oscar Health

Location: Los Angeles, California, United States

Job Type: Full-Time

Category: Product Design / Operations Technology

Date Posted: 2026-09-14

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

Remote Status: Hybrid

🚀 Role Summary

• Drive the end-to-end design process for mission-critical internal tools that power Oscar's insurance and care operations.

• Leverage AI-enabled design practices using tools like Claude and Codex to accelerate discovery, ideation, and prototyping for complex workflows.

• Develop a deep understanding of internal user needs and operational environments to create clear, effective, and scalable user experiences.

• Collaborate closely with Product Management, Engineering, Research, and operational teams to define product direction and deliver impactful solutions.

• Contribute to a consistent and high-quality user experience across Oscar's internal product ecosystem by adhering to and improving design systems and standards.

📝 Enhancement Note: This role is positioned within Product Design but has a strong emphasis on "Internal Tools" and "Operations," indicating a significant focus on Revenue Operations (RevOps) and Sales Operations enablement through technology. The core responsibilities revolve around designing systems that streamline complex business processes, a hallmark of effective operations technology.

📈 Primary Responsibilities

• Lead the design process for complex internal tools, from problem definition and discovery through to detailed interaction design, implementation, and iteration.

• Map intricate workflows and systems to identify operational pain points, inefficiencies, dependencies, and opportunities for simplification and automation.

• Partner with Product Managers and Engineers to define product vision, establish measurable goals, and contribute to strategic roadmaps for internal operational platforms.

• Design data-dense interfaces and configurable workflows that support critical business functions such as claims management, risk adjustment, and provider network management.

• Utilize AI tools (Claude, Codex) to clarify user and business needs, explore potential solutions, identify edge cases, and generate realistic prototypes early in the design cycle.

• Apply rigorous design judgment to AI-generated outputs, refining structure, behavior, accessibility, and visual quality to meet high standards.

• Create and present prototypes, lead design workshops, and facilitate product vision activities to build team alignment and clarity on complex operational challenges.

• Collaborate closely with engineers during implementation to ensure the shipped experience meets the intended quality, technical constraints, and scalability requirements.

• Contribute to and improve shared design system components, patterns, and standards, ensuring consistency across Oscar's internal product suite.

• Uphold and apply Oscar's brand guidelines, accessibility standards, and design principles across all product experiences.

• Document and share best practices, useful prompts, and workflows for leveraging AI within the product design process.

• Ensure all AI usage complies with Oscar’s privacy, security, and member-data requirements.

📝 Enhancement Note: The emphasis on "complex workflows," "data-rich," and "technically complex" strongly suggests a focus on designing for operational efficiency and enablement. The role requires translating intricate business logic into user-friendly interfaces, a key function for supporting Sales Operations, Customer Success Operations, and broader GTM functions.

🎓 Skills & Qualifications

Education:

• Bachelor's degree in Design, Human-Computer Interaction (HCI), Computer Science, or a related field, or equivalent practical experience. Experience:

• 4+ years of professional experience in Product Design, UX Design, or a closely related field, with a proven track record of designing and shipping complex web, mobile, SaaS, or internal-tool experiences.

• At least 2 years of experience owning and managing relationships with cross-functional stakeholders, including Product Managers, Engineers, and operational teams.

• Demonstrated experience leading product design initiatives autonomously, from initial problem definition through to launch and subsequent iterations.

• Experience working in ambiguous or complex product areas, requiring strong problem-solving and strategic thinking. Required Skills:

• Strong portfolio showcasing product thinking, systems thinking, interaction design, and visual craft, with specific examples of complex internal tools or SaaS applications.

• Proficiency in translating requirements, business goals, user research findings, and technical constraints into clear, intuitive, and effective product experiences.

• Active and proficient use of AI-assisted design tools such as Claude, Codex, or comparable technologies within a product design workflow.

• Ability to effectively explain the role of AI in the design process, highlighting where it was beneficial, where human judgment was crucial, and how the final output was shaped.

• Excellent written, visual, and verbal communication skills, with the ability to articulate design decisions and rationale clearly to diverse audiences.

• Experience partnering closely with Product and Engineering teams to define problems, evaluate solutions, and drive measurable outcomes. Preferred Skills:

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

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

• Experience designing data-dense interfaces, configurable workflows, permission systems, or multi-role systems.

• Proven ability to simplify fragmented products, workflows, or complex product ecosystems.

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

• Experience creating realistic or coded prototypes for user testing and stakeholder presentations.

• Familiarity with front-end development concepts such as components, states, responsive behavior, and accessibility standards.

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

• Experience using animated prototypes, working software, or user-flow diagrams to effectively communicate product direction.

• Experience contributing reusable prompts, patterns, components, or workflows to a broader design team.

• Interest in accessibility, design ethics, and the responsibilities associated with designing healthcare products.

• A curious, humble, determined, and feedback-open working style.

📝 Enhancement Note: The requirement for 4+ years of experience and the emphasis on "complex web, mobile, SaaS, or internal-tool experiences" positions this as a senior-level role. The specific mention of "internal tools" and "operational environments" is a strong indicator for candidates with experience in designing for Sales Operations, RevOps, or GTM enablement platforms. The AI tool requirements are cutting-edge and indicate a forward-thinking design practice.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least two examples of designing and shipping complex web, mobile, SaaS, or internal-tool experiences, demonstrating end-to-end ownership.

• Highlight a deep understanding of product thinking, systems thinking, and interaction design principles applied to solve user and business problems.

• Include detailed case studies that illustrate your process for problem definition, user research, workflow mapping, ideation, prototyping, and final design delivery.

• Demonstrate experience in translating complex requirements, business goals, and technical constraints into intuitive and effective user interfaces.

• Present examples of how you have collaborated with Product and Engineering teams to define product direction and deliver measurable outcomes. Process Documentation:

• Provide clear documentation of your design process, including how you approach discovery, research, synthesis, ideation, prototyping, and validation.

• Detail your methodology for mapping complex workflows and identifying operational inefficiencies or opportunities for improvement within those workflows.

• Showcase how you've utilized AI-assisted tools (Claude, Codex) to enhance your design process, from initial problem clarification to prototype generation, and how you've refined AI outputs.

• Include examples of how you measure the impact of your designs, demonstrating an understanding of key performance indicators (KPIs) relevant to internal tools and operational efficiency.

📝 Enhancement Note: For operations-focused roles, a portfolio is critical. Candidates should emphasize case studies that demonstrate their ability to untangle complex operational processes, design for efficiency, and quantify the impact of their design solutions on user productivity and business outcomes. The AI component is a unique differentiator that should be clearly articulated.

💵 Compensation & Benefits

Salary Range:

• The base pay for this role is between $149,040.00 and $195,615.00 per year. Benefits:

• Comprehensive medical, dental, and vision insurance plans.

• 11 paid holidays, paid sick time, and paid parental leave.

• 401(k) plan participation with company match (implied, typical for such plans).

• Life and disability insurance coverage.

• Paid wellness time and wellness reimbursements.

• Unlimited vacation program, encouraging work-life balance.

• Company equity grants, offering ownership and potential for long-term financial growth.

• Annual performance bonuses, tied to individual and company success. Working Hours:

• This role is based on a standard 40-hour work week.

• A hybrid work schedule is required, with 3 days in the office per week. Thursdays are designated as a mandatory in-office day for team meetings and events, offering flexibility on the other two office days.

📝 Enhancement Note: The salary range provided is competitive for a Senior Product Designer role in the Los Angeles area, especially within the tech and healthcare sectors. The comprehensive benefits package, including equity and performance bonuses, indicates a strong total compensation offering. The hybrid model with specific in-office days is typical for fostering collaboration while allowing some flexibility.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance Technology (Insurtech)

Company Size: Oscar Health is a significant player in the health insurance market, employing a substantial number of individuals. The company has grown considerably since its founding, indicating a dynamic and evolving work environment.

Founded: 2012

Company Description: Oscar Health is a technology-driven health insurance company focused on improving the member experience through its integrated platform. They aim to provide a more personalized, efficient, and consumer-friendly approach to healthcare.

Team Structure:

• The Product Design team is part of the broader Product organization, likely working in close collaboration with Product Management and Engineering.

• This specific role is on the "Internal Tools" design team, suggesting a dedicated focus on building and improving the technology that empowers Oscar's internal operational staff.

• The team structure likely involves a Product Design Director overseeing multiple Senior Product Designers, each potentially focusing on different internal tool domains.

• Cross-functional collaboration is a cornerstone, with designers working alongside Product Managers, Engineers, Researchers, Data Analysts, Clinicians, and operational teams. Methodology:

• AI-Enabled Design Practice: Oscar is actively integrating AI tools (Claude, Codex) into its design workflow for problem clarification, workflow exploration, risk identification, and rapid prototyping.

• Data-Driven Decision Making: The role emphasizes using research, data, hypotheses, and experimentation to inform design decisions and measure product impact.

• Systems Thinking: A core methodology involves mapping complex workflows and systems to understand interdependencies, identify bottlenecks, and design holistic solutions.

• Agile Development & Iteration: The design process moves from discovery through delivery and iteration, suggesting an agile or iterative approach to product development.

Company Website: https://hioscar.com/

📝 Enhancement Note: Oscar's commitment to technology and its unique position as an Insurtech company shape its culture. The emphasis on AI integration is a significant differentiator, suggesting a forward-thinking approach to design and operations. The internal tools team is crucial for operational efficiency, making this role vital to the company's success in delivering healthcare services.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, signifying a level of autonomy, strategic input, and ownership. Senior designers are expected to lead complex projects, mentor junior team members (implicitly), and influence product direction. The focus on internal operational tools places this role at the intersection of design and business process optimization.

Reporting Structure: The role reports to a Product Design Director. This provides a clear line of management and mentorship, with opportunities for strategic guidance and career development discussions.

Operations Impact: The work directly impacts the efficiency, productivity, and effectiveness of Oscar's core insurance and care operations teams. By designing better internal tools, this role contributes to smoother claims processing, improved patient care coordination, more accurate risk adjustment, and better network management, all of which are critical for the company's financial health and member satisfaction. The AI integration aspect also positions the role at the forefront of operational technology innovation.

Growth Opportunities:

• Skill Specialization: Deepen expertise in designing complex operational workflows, data-dense interfaces, and AI-assisted design practices.

• Leadership Development: Potential to lead design initiatives, mentor junior designers, and contribute to the strategic direction of the internal tools product portfolio.

• Cross-functional Influence: Grow influence across Product, Engineering, and Operations by delivering impactful solutions and fostering strong collaborative relationships.

• Industry Expertise: Gain specialized knowledge in the healthcare and insurance industries, particularly in operational challenges and regulatory environments.

• AI Design Leadership: Become a key contributor to Oscar's AI-enabled design practice, shaping how AI is responsibly and effectively used in product development.

📝 Enhancement Note: This role offers significant growth potential for designers interested in operational efficiency and the application of emerging technologies like AI in a regulated industry. The path from Senior Designer could lead to Principal Designer, Design Lead, or even management roles within the product organization.

🌐 Work Environment

Office Type: Hybrid work model, with a requirement to be in the Marina Del Rey office 3 days per week.

Office Location(s): Marina Del Rey, California. This location offers access to a vibrant tech hub and a significant talent pool.

Workspace Context:

• Collaborative Environment: The hybrid model, with designated in-office days (including a mandatory Thursday), is designed to foster in-person collaboration, team meetings, and spontaneous interactions vital for design brainstorming and problem-solving.

• Operations Tool & Technology Access: Designers will have access to industry-standard design tools (Figma) and cutting-edge AI tools (Claude, Codex), along with the necessary infrastructure to support a hybrid work setup.

• Cross-Functional Interaction: The workspace will facilitate regular interaction with product managers, engineers, researchers, data partners, and operational stakeholders, promoting a holistic understanding of business needs and user challenges.

Work Schedule: A standard 40-hour work week is expected. The hybrid schedule provides some flexibility in choosing office days, allowing operations professionals to balance in-office collaboration with remote focus time.

📝 Enhancement Note: The Marina Del Rey office location is a key aspect for candidates in the Los Angeles area. The hybrid setup is a common and often preferred model for design and operations roles, aiming to capture the benefits of both remote focus and in-office collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review applications and portfolios to assess alignment with the role's core requirements.

• Design Challenge/Portfolio Review: Candidates will likely present their portfolio, discussing specific case studies that highlight their product thinking, systems thinking, interaction design, and experience with complex workflows and AI tools. This may involve a dedicated presentation or a deep dive into selected projects.

• Cross-Functional Interviews: Interviews with Product Managers, Engineers, and potentially other designers or operational stakeholders to assess collaboration skills, problem-solving abilities, and understanding of technical constraints and business needs.

• Hiring Manager/Director Interview: A final interview with the Product Design Director to discuss strategic alignment, career aspirations, and cultural fit.

Portfolio Review Tips:

• Highlight Operations Focus: Clearly showcase projects that involve designing for complex operational workflows, internal tools, or enterprise software. Emphasize how your designs improved efficiency, reduced errors, or streamlined processes.

• Demonstrate Systems Thinking: Use diagrams, flowcharts, or detailed descriptions to illustrate how your designs fit into a larger system or ecosystem of tools.

• Showcase AI Integration: If possible, include examples of how you've used AI tools in your design process. Explain the specific prompts used, the AI's contribution, and how you refined its output to achieve the final result. Quantify any efficiency gains or improvements in fidelity/speed.

• Quantify Impact: Wherever possible, include metrics or data that demonstrate the positive impact of your designs on users or business outcomes (e.g., reduced task completion time, increased adoption rates, decreased error rates).

• Tell a Story: For each case study, structure it as a narrative: the problem, your approach, your solutions, the challenges, and the results. Explain your rationale and decision-making process clearly.

Challenge Preparation:

• Anticipate Workflow Problems: Be prepared to discuss how you would approach designing solutions for common operational challenges in insurance or healthcare, such as claim adjudication, patient intake, or provider credentialing.

• AI Prompting Skills: Practice articulating problems and workflows in a way that would be effective for AI tools to process. Think about how you would guide an AI to explore different scenarios or generate specific UI elements.

• Systems Thinking Exercises: Be ready to analyze a hypothetical complex system or workflow and identify potential areas for design intervention and improvement.

• Communication Clarity: Practice articulating complex design concepts and decisions concisely and persuasively, especially when discussing technical constraints or AI-generated outputs.

📝 Enhancement Note: The emphasis on AI tools and complex operational workflows means candidates should be prepared to articulate their experience with these specific areas. The portfolio should be curated to prominently feature relevant projects, showcasing not just aesthetic skills but also strategic problem-solving and process optimization capabilities.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI design, prototyping, and collaboration. Proficiency in creating comprehensive design states, leveraging components, and ensuring design system alignment is essential.

• AI Design Tools (Claude, Codex): Active and proficient use of these AI tools is a requirement for clarifying problems, exploring workflows, identifying risks, and generating realistic prototypes.

• Prototyping Tools (built into Figma or others): For creating interactive prototypes to test assumptions and communicate design direction.

Analytics & Reporting:

• While not explicitly stated as a primary design tool, familiarity with how design impacts analytics and reporting is crucial. This includes understanding how design choices affect user behavior tracking, conversion rates, and performance metrics within operational systems.

• Experience with data visualization tools or principles may be beneficial for designing data-dense interfaces. CRM & Automation:

• Familiarity with CRM systems (e.g., Salesforce, though not specified) and automation platforms is advantageous, as internal tools often integrate with or complement these systems. Understanding how design can facilitate automation and improve CRM data quality is a plus.

• Experience designing for systems that manage complex workflows, permissions, and multi-role access is highly relevant.

📝 Enhancement Note: The specific mention of Claude and Codex as AI tools is a strong indicator of Oscar's investment in AI-driven design. Candidates should be prepared to discuss their experience with these or similar large language model (LLM) based AI assistants for design tasks. Figma is a standard for modern UI design.

👥 Team Culture & Values

Operations Values:

• Member-Centricity: While this role focuses on internal tools, the ultimate goal is to improve the experience and outcomes for Oscar's health insurance members. Designs should indirectly support this mission.

• Data-Driven Approach: Decisions are informed by data, research, and experimentation. Operations professionals are expected to leverage insights to drive improvements.

• Efficiency & Optimization: A strong emphasis on streamlining processes, reducing waste, and maximizing productivity through effective tool design.

• Collaboration & Transparency: Working effectively across teams, sharing knowledge, and being open to feedback are highly valued.

• Innovation & Adaptability: Embracing new technologies like AI and being willing to adapt to evolving business needs and industry trends.

Collaboration Style:

• Cross-functional Integration: Designers are expected to be integral members of product teams, working hand-in-hand with Product Managers, Engineers, and operational experts.

• Process Review & Feedback Culture: Regular design critiques and feedback sessions are likely part of the team's process, fostering continuous improvement and shared learning.

• Knowledge Sharing: Contributing to team best practices, documenting learnings, and sharing insights, particularly around AI-assisted design.

📝 Enhancement Note: The culture at Oscar, particularly within its operational and product teams, likely prioritizes impact, efficiency, and collaborative problem-solving. The integration of AI suggests a culture that embraces innovation and seeks to leverage technology for operational advantage.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of Operational Workflows: Designing for intricate, multi-step processes within a regulated industry like healthcare can be challenging, requiring deep understanding and meticulous attention to detail.

• Balancing Immediate Delivery with Long-Term Vision: The need to deliver polished, functional tools quickly while also maintaining a coherent and scalable long-term product direction.

• Navigating Technical Constraints: Working within the limitations of existing technology stacks and engineering resources without compromising user experience or strategic goals.

• Responsible AI Implementation: Ensuring that AI tools are used ethically, securely, and in compliance with all relevant regulations, while also maximizing their benefits.

• User Adoption of New Tools/Processes: Encouraging internal users to adopt new tools and workflows, which may require change management and strong user advocacy.

Learning & Development Opportunities:

• Advanced AI Design Skills: Becoming an expert in leveraging AI tools for sophisticated design tasks and contributing to the team's AI strategy.

• Deep Domain Expertise: Developing specialized knowledge in healthcare operations, insurance processes, and regulatory compliance.

• Systems Design Mastery: Enhancing skills in designing complex, interconnected systems and understanding their impact on organizational efficiency.

• Leadership and Mentorship: Opportunities to guide product strategy, mentor junior designers, and potentially lead specific product areas or initiatives.

• Industry Trends: Staying abreast of emerging trends in product design, AI, and the Insurtech landscape.

📝 Enhancement Note: This role presents a unique opportunity to work at the cutting edge of AI in design within a critical industry. The challenges are significant but come with substantial growth potential for ambitious designers.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design a complex workflow for internal users. What were the key challenges, and how did your design address them?" (Focus on process mapping, user needs, and impact.)

• "How have you used AI tools like Claude or Codex in your design process? Can you walk us through a specific example where AI helped you explore ideas or create a prototype, and how you refined its output?" (Be ready to detail prompts, AI's contribution, and your critical judgment.)

• "How do you balance the need for immediate delivery of features with maintaining a coherent long-term product strategy for complex systems?" (Discuss prioritization, modular design, and roadmapping.)

• "Tell me about a time you had to work with significant technical constraints. How did you navigate them while still delivering a valuable user experience?" (Highlight problem-solving and compromise.) Company & Culture Questions:

• "What interests you about Oscar Health, particularly our approach to using technology and AI in healthcare?" (Research Oscar's mission, values, and recent news.)

• "How do you approach collaboration with product managers and engineers, especially when dealing with complex operational requirements?" (Emphasize partnership, communication, and shared ownership.)

• "How do you ensure your designs are accessible and comply with industry standards, especially in a regulated field like healthcare?" (Showcase awareness of accessibility principles and regulatory considerations.) Portfolio Presentation Strategy:

• Structure for Impact: Begin with a high-level overview of the project and its business goals. Clearly articulate the problem, your role, and the key challenges.

• Process Over Polish: Detail your design process, especially how you mapped complex workflows, identified pain points, and leveraged AI. Use visuals like flowcharts, wireframes, and prototypes to illustrate your journey.

• Quantify Results: Wherever possible, present metrics that demonstrate the positive impact of your designs on user efficiency, productivity, or business outcomes.

• AI Integration Narrative: Dedicate a segment to explaining your use of AI tools. Show specific examples of prompts, AI-generated outputs, and how your expertise shaped the final design.

• Concise and Engaging: Keep your presentation focused and engaging. Be prepared to answer detailed questions about your decisions and rationale. Practice your delivery to ensure clarity and confidence.

📝 Enhancement Note: Candidates should prepare to demonstrate not only their design craft but also their strategic thinking, operational understanding, and ability to integrate novel technologies like AI into their workflow. The interview process will likely assess these capabilities deeply.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Greenhouse.

• Curate Your Portfolio: Select 2-3 of your strongest projects that best showcase your experience with complex internal tools, workflow design, systems thinking, and AI integration. Ensure these projects clearly articulate the problem, your process, your solutions, and the measurable impact.

• Optimize Your Resume: Tailor your resume to highlight keywords and responsibilities mentioned in the job description, such as "Product Design," "UX Design," "Internal Tools," "SaaS," "Systems Thinking," "Workflow Mapping," and "AI-Assisted Design." Quantify achievements whenever possible.

• Prepare Your Presentation: Practice walking through your portfolio case studies, focusing on your design process, your rationale, and the outcomes. Be ready to specifically address your experience with AI tools and complex operational challenges.

• Research Oscar Health: Familiarize yourself with Oscar's mission, values, products, and recent news, particularly their focus on technology and AI. Understand their position in the healthcare industry.

⚠️ 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.