Product Designer, ICHRA at Oscar Health

📍 Job Overview

Job Title: Product Designer, ICHRA

Company: Oscar Health

Location: Boston, Massachusetts, United States

Job Type: Full-Time

Category: Product Design / UX/UI Operations

Date Posted: August 14, 2026

Experience Level: Mid-Senior Level (2-5 years)

Remote Status: Fully Remote (Boston, MA residents)

🚀 Role Summary

Design and deliver innovative user experiences for Oscar's ICHRA (Individual Coverage Health Reimbursement Arrangement) tooling within the Lucie Marketplace, a complex enterprise software platform.
Drive product strategy and execution by collaborating closely with cross-functional teams including Product Management, Engineering, Research, Data Science, and Operations stakeholders.
Champion user needs and advocate for a consistent, scalable, and intuitive user experience across the entire Lucie suite, from discovery through high-fidelity delivery.
Leverage AI-assisted tools like Claude Code alongside Figma to streamline the design-to-engineering workflow and enhance design process efficiency.

📝 Enhancement Note: While the title is "Product Designer," the responsibilities and required experience lean towards a specialized role within operations, focusing on the design and implementation of complex enterprise software that directly impacts business operations and user management within the health insurance sector. The emphasis on ICHRA tooling and enterprise software design suggests a need for operational understanding beyond standard consumer product design.

📈 Primary Responsibilities

Define and design end-to-end user experiences for Oscar’s ICHRA products, enabling employers to effectively manage health plan contributions for their employees.
Conduct user research and usability testing to gather actionable insights, translating them into informed design decisions that address user pain points and drive product improvements.
Own the product design process from concept through to high-fidelity delivery, ensuring seamless integration with technical constraints and business objectives.
Collaborate with Senior Product Designers, Product Managers, Tech Leads, Engineers, Data Scientists, and Business Stakeholders to ensure strategic alignment and successful solution development.
Contribute to and maintain Oscar’s design language system (Anatomy), ensuring visual consistency and brand integrity across all product interfaces.
Partner with other product designers across the organization, providing and receiving constructive feedback during design critiques to foster a collaborative and high-performing design team.
Translate complex requirements, goals, and research findings into simple, intuitive, and visually compelling user interfaces for web and mobile platforms.
Ensure compliance with all applicable laws and regulations within the healthcare industry.

📝 Enhancement Note: The responsibilities emphasize a blend of strategic product thinking, user advocacy, and hands-on design execution within a regulated industry. The focus on ICHRA tooling and employer-facing features suggests a need for an understanding of B2B/enterprise software design principles and operational workflows.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience, is highly recommended for understanding design principles and technical integration.

Experience:

4+ years of progressive experience in Product Design, UX Design, or a related field.
Proven track record of designing and shipping complex web and mobile interfaces, with at least two concrete examples demonstrating successful product launches.
Minimum of 2 years of direct experience managing and collaborating with diverse stakeholders, including Product Managers, Engineers, and business leaders. Required Skills:
Expertise in Product Design principles and UX methodologies, with a strong ability to translate user needs into intuitive interfaces.
Proficiency in visual design, with a strong portfolio showcasing complex enterprise software, data-intensive platforms, or workforce management tool design.
Experience conducting user research, usability testing, and translating findings into actionable design improvements.
Demonstrated ability to manage cross-functional stakeholder relationships, drive alignment, and communicate design rationale effectively.
Advanced proficiency with design tools such as Figma, and familiarity with AI-assisted design tools like Claude Code.
Experience with design systems and a proven ability to contribute to or maintain them. Preferred Skills:
Prior experience within the healthcare industry, understanding its unique regulatory and user landscape.
Proficiency in storytelling techniques, including the creation of animated prototypes and detailed user flow diagrams.
Interest in and understanding of design ethics, accessibility standards, and their application in healthcare.
Evidence of contributions to internal tools, system workflows, and power-user interfaces.
Proven ability to navigate and overcome technical constraints to deliver effective design solutions.
Experience with user research and prototyping methodologies.
Ability to translate complex requirements, goals, and research into simple and useful UI designs.

📝 Enhancement Note: The emphasis on "complex enterprise software," "data-intensive platforms," and "workforce management tools" strongly indicates that candidates with experience in B2B SaaS or enterprise-level product design will be highly valued. The preference for healthcare experience and interest in design ethics highlights the specific domain of this role.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

Showcase at least two distinct projects demonstrating the end-to-end design process for complex web and mobile interfaces, ideally within enterprise software, B2B SaaS, or data-intensive platforms.
Clearly articulate your role, the problem statement, your design process, key decisions made, and the measurable impact of your solutions.
Include examples of user research, wireframing, prototyping, and final UI designs.
Highlight experience in stakeholder management and how you navigated feedback and collaboration.
Demonstrate an understanding of design systems and how your work aligns with or contributes to them. Process Documentation:
For each portfolio piece, clearly document the discovery phase, including user research methodologies and insights gathered.
Detail the iterative design and prototyping phases, showcasing how user feedback influenced the design direction.
Explain the process of collaborating with engineering and product management to ensure successful implementation and delivery of the final product.
Include metrics or outcomes that demonstrate the impact of your design solutions, such as user adoption, efficiency gains, or task completion rates.

📝 Enhancement Note: A strong portfolio is critical for this role, particularly one that exhibits experience with complex systems and enterprise-level problem-solving. The ability to articulate the "why" behind design decisions and demonstrate measurable impact will be key. Explicitly showing experience with B2B/enterprise software design is crucial.

💵 Compensation & Benefits

Salary Range: $123,372.00 - $161,925.75 per year

Benefits:

Comprehensive Medical, Dental, and Vision benefits.
Unlimited Vacation Program: Empowers employees to take time off as needed, promoting work-life balance.
Company Equity Grants: Opportunity to share in the company's growth and success.
Annual Performance Bonuses: Rewarding individual and company achievements.
11 Paid Holidays: Standard national holidays observed.
Paid Sick Time: For personal health and well-being.
Paid Parental Leave: Supporting new parents.
401(k) Plan Participation: Retirement savings plan.
Life Insurance: Financial protection for beneficiaries.
Disability Insurance: Income protection in case of extended illness or injury.
Paid Wellness Time and Reimbursements: Encouraging and supporting employee well-being initiatives.

Working Hours: The role is specified as full-time, and while the exact hours are not detailed, a standard 40-hour work week is typical in the US for such roles. The fully remote nature offers flexibility.

📝 Enhancement Note: The salary range provided is competitive for a Product Designer role with 4+ years of experience in a high-cost-of-living area like Boston. The benefits package is robust and aligns with typical offerings for tech companies, with particular emphasis on wellness and work-life balance (unlimited vacation, paid wellness time). The inclusion of equity and annual bonuses suggests a performance-driven culture.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health Insurance Technology / HealthTech. Oscar Health is a disruptive force in the health insurance market, leveraging technology to create a more member-centric and accessible healthcare experience.

Company Size: While not explicitly stated in the raw data, Oscar Health is a significant player in the health insurance market, indicating a medium to large-sized organization with established processes and a growing team. The presence of multiple derived locations suggests a distributed workforce.

Founded: Oscar was founded in 2012, positioning it as a relatively modern tech-driven health insurance provider that has evolved from a startup to a more established company. This history suggests a culture that balances innovation with the need for robust, scalable systems.

Team Structure:

The Product Design team likely operates within a larger Product, Design, Data, and Engineering organization, reporting to the SVP, Product, Design, Data.
This role involves close partnership with Product Managers, Engineers, Researchers, Data Scientists, and Operations stakeholders, indicating a highly collaborative and cross-functional team environment.
The specific focus on ICHRA tooling suggests the existence of specialized product pods or squads dedicated to specific areas of the Lucie Marketplace. Methodology:
Oscar emphasizes a "full stack technology platform" approach, suggesting a data-driven and engineering-centric methodology.
The role requires a blend of agile execution (designing and shipping features) and strategic thinking (defining user experiences and driving product strategy).
A strong focus on user empathy, research, and iterative design is expected.
The integration of AI-assisted tools highlights a forward-thinking approach to design and development workflows.

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

📝 Enhancement Note: Oscar Health's mission to make healthcare affordable and accessible through technology points to a culture that values innovation, user-centricity, and operational efficiency. The company's growth suggests a dynamic environment where established processes are balanced with a need for continuous improvement and adaptation.

📈 Career & Growth Analysis

Operations Career Level: This Product Designer role, with 4+ years of experience and direct stakeholder management, is positioned at a mid-to-senior level. It requires independent ownership of design processes and significant cross-functional collaboration, indicating a role that contributes to strategic decision-making within its domain. The focus on ICHRA tooling places it within a specialized, operations-critical segment of the business.

Reporting Structure: The role reports into the SVP, Product, Design, Data. This high-level reporting structure suggests visibility and the potential for significant impact. The designer will work closely with a Senior Product Designer specifically focused on ICHRA.

Operations Impact: The Product Designer's work directly influences the efficiency and usability of Oscar's ICHRA offerings, which are critical for employer clients managing health plan contributions. Well-designed tools can lead to increased adoption, reduced administrative burden for employers, improved employee experience, and ultimately, greater market competitiveness for Oscar. The role bridges the gap between complex operational requirements and user-friendly design.

Growth Opportunities:

Specialization: Deepen expertise in designing for complex B2B/enterprise software, particularly within the regulated health insurance sector, becoming a go-to expert for ICHRA and related functionalities.
Leadership: Progress to a Senior Product Designer role, potentially leading design efforts for specific product areas or mentoring junior designers.
Cross-functional Development: Gain deeper understanding of product management, engineering challenges, data analysis, and operational workflows, enhancing overall product strategy contribution.
Design System Expansion: Contribute to the evolution and expansion of Oscar's design language system, "Anatomy," potentially leading initiatives within specific product domains.

📝 Enhancement Note: The growth opportunities are tied to both design specialization and broader product/operations understanding. The reporting structure to an SVP suggests potential for high-impact projects and visibility within the organization.

🌐 Work Environment

Office Type: This is a fully remote position. While Oscar has hub offices, the role is open to candidates residing in Boston, MA, and can be performed remotely. Future hybrid models may be introduced, but the current offering is remote.

Office Location(s): The role is based in Boston, MA, though remote. Oscar Health has other hub locations as well, indicating a distributed workforce model.

Workspace Context:

As a remote role, the primary workspace will be the employee's home office, requiring self-discipline and effective remote collaboration tools.
The remote setup necessitates strong communication skills and proactive engagement with team members and stakeholders across different locations.
Access to Oscar's digital tools and platforms will be essential for day-to-day work, including Figma, Claude Code, and other collaboration software.
The role demands an environment conducive to focused design work, user research, and virtual collaboration sessions.

Work Schedule: Standard full-time hours (typically 40 hours per week) are expected. While remote, maintaining consistent availability for team meetings, design critiques, and stakeholder discussions during core business hours is important for effective cross-functional collaboration.

📝 Enhancement Note: The fully remote nature of this position offers significant flexibility but requires strong self-management and communication skills. Understanding how to effectively collaborate virtually with distributed teams is key.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A recruiter or hiring manager will review your application and resume, looking for alignment with the core requirements and experience.
Portfolio Review & Discussion: You will likely be asked to present your portfolio, detailing 2-3 relevant projects. This will involve discussing your design process, problem-solving approach, user research, stakeholder management, and the impact of your work. Be prepared to answer questions about your experience with complex enterprise software and ICHRA or similar financial/operational tools.
Design Challenge/Exercise: A practical design exercise may be given, either take-home or conducted during an interview, to assess your problem-solving skills, design thinking, and ability to translate requirements into tangible design solutions. This could involve a specific challenge related to ICHRA or a similar complex system.
Cross-functional Interviews: You will likely meet with Product Managers, Engineers, and potentially other designers or operations stakeholders to assess your collaboration style, technical understanding, and cultural fit.
Final Interview: A meeting with the SVP, Product, Design, Data, or another senior leader to discuss your overall fit, strategic thinking, and long-term career aspirations.

Portfolio Review Tips:

Focus on Impact: Quantify your achievements whenever possible. Use metrics to demonstrate the success of your designs (e.g., improved user adoption, reduced error rates, increased task completion efficiency).
Showcase Process: Clearly articulate your design process for each project, highlighting how you moved from problem definition to solution. Emphasize user research, iterative design, and collaboration.
Enterprise Context: For this role, explicitly highlight projects involving complex enterprise software, B2B platforms, or data-intensive applications. Explain the unique challenges and considerations for designing such systems.
ICHRA Relevance: If you have experience with financial tools, HR platforms, or healthcare administration systems, make sure these projects are prominently featured. If not, draw parallels to similar complex systems you have designed.
Visual Polish: Ensure your portfolio is well-organized, visually appealing, and easy to navigate. High-fidelity mockups and interactive prototypes are beneficial.

Challenge Preparation:

Understand the Domain: Research ICHRA, employer health benefits, and the broader health insurance landscape. Understand the key stakeholders (employers, employees, brokers) and their potential pain points.
Focus on Workflow: Practice designing for complex workflows and user journeys. Think about how to simplify intricate processes and provide clear guidance to users.
Data Interpretation: Be prepared to interpret data and requirements to inform your design decisions.
AI Tool Integration: If an AI tool is mentioned, consider how you might leverage it in a design challenge to improve efficiency or explore solutions.

📝 Enhancement Note: The interview process is likely to be rigorous, with a strong emphasis on portfolio presentation and practical design skills. Candidates should be prepared to demonstrate their ability to handle complex enterprise problems and collaborate effectively within a cross-functional team.

🛠 Tools & Technology Stack

Primary Tools:

Figma: The core design tool for wireframing, prototyping, and high-fidelity UI design. Expect to create and maintain design files within Figma.
Claude Code: Mentioned as an AI-assisted tool to streamline the design-to-engineering process. Familiarity or a willingness to learn and leverage AI in design workflows is expected.
Prototyping Tools: Beyond Figma, other tools like InVision or Principle may be used for advanced prototyping or animation, especially for storytelling.

Analytics & Reporting:

While not explicitly listed as a designer's direct tool, understanding how to interpret data from analytics platforms (e.g., Google Analytics, Mixpanel, Amplitude) to inform design decisions is crucial. Designers will likely work with data scientists and product managers who utilize these tools. CRM & Automation:
Not directly applicable to the designer's primary toolset, but understanding how design impacts CRM systems or automated workflows within the Lucie Marketplace could be beneficial.

📝 Enhancement Note: Proficiency in Figma is a must. The mention of Claude Code suggests a forward-thinking approach to design tools and an expectation that candidates are open to or already utilizing AI in their design process. Understanding the broader tech stack and how design integrates with it is advantageous.

👥 Team Culture & Values

Operations Values:

User-Centricity: A deep commitment to understanding and advocating for the needs of Oscar's users, particularly employers managing health benefits.
Collaboration: A strong emphasis on working effectively with cross-functional partners to achieve shared goals. This includes giving and receiving feedback constructively.
Data-Driven Decision Making: Utilizing research and analytics to inform design choices and measure impact.
Efficiency & Scalability: Designing solutions that are not only intuitive but also efficient to build, maintain, and scale across the Lucie suite.
Innovation: Embracing new technologies and methodologies, such as AI-assisted tools, to improve design processes and outcomes.

Collaboration Style:

Cross-functional Partnership: The role requires seamless collaboration with Product Managers, Engineers, Researchers, and Data Scientists. This involves regular communication, shared understanding of goals, and joint problem-solving.
Design Critiques: An active participation in design critiques is expected, fostering a culture of continuous improvement and shared learning within the design team.
Open Communication: A transparent and open communication style is vital for navigating complex projects and ensuring alignment across diverse teams and stakeholders.

📝 Enhancement Note: The culture at Oscar Health appears to be collaborative, innovative, and user-focused, with a strong emphasis on leveraging technology to achieve its mission. Designers are expected to be proactive communicators and team players.

⚡ Challenges & Growth Opportunities

Challenges:

Complexity of ICHRA: Designing for the intricacies of ICHRA and employer benefits management requires a deep understanding of complex financial and regulatory frameworks.
Balancing User Needs with Business Requirements: Effectively translating diverse user needs and business objectives into a cohesive and functional design.
Cross-functional Alignment: Ensuring all stakeholders are aligned on the design strategy and implementation across different departments.
Remote Collaboration: Maintaining strong team cohesion and effective communication in a fully remote environment.
Evolving Technology: Keeping pace with advancements in design tools, AI, and the broader tech landscape.

Learning & Development Opportunities:

Domain Expertise: Gaining in-depth knowledge of the health insurance industry, specifically employer benefits and ICHRA regulations.
Advanced Design Skills: Developing expertise in designing for complex enterprise systems, data visualization, and potentially leading design initiatives.
AI in Design: Becoming proficient in leveraging AI tools for enhanced design efficiency and exploration.
Leadership Development: Opportunities to mentor junior designers, lead design projects, and contribute to the strategic direction of the product design team.

📝 Enhancement Note: The role presents challenges inherent in designing for complex, regulated industries and remote work environments. However, these challenges are coupled with significant opportunities for specialized domain expertise and career advancement.

💡 Interview Preparation

Strategy Questions:

"Describe a time you designed a complex enterprise software feature. What were the main challenges, and how did you address them?" (Focus on process, user research, stakeholder management, and outcomes.)
"How do you approach balancing the needs of multiple stakeholders (e.g., employers, employees, internal operations teams) when designing a feature?" (Highlight your communication, negotiation, and user advocacy skills.)
"Walk us through a project where you had to navigate significant technical constraints. How did your design adapt, and what was the result?" (Demonstrate problem-solving and practical design execution.)
"How would you use user research to inform the design of an ICHRA management tool for employers?" (Showcase your understanding of research methodologies and their application to operational tools.) Company & Culture Questions:
"What interests you about Oscar Health and our mission to make healthcare affordable and accessible?" (Show your understanding of the company's mission and values.)
"How do you contribute to a collaborative design team environment, especially in a remote setting?" (Provide examples of your teamwork and communication style.)
"How do you ensure your designs are scalable and align with a company's design system?" (Demonstrate your understanding of design systems and long-term thinking.) Portfolio Presentation Strategy:
Structure for Impact: For each portfolio piece, follow a clear narrative: Problem -> Your Role -> Process -> Solution -> Impact.
Quantify Results: Wherever possible, use metrics to demonstrate the success of your designs. Focus on business outcomes and user experience improvements.
Highlight Enterprise Experience: Explicitly call out projects that involved complex systems, B2B platforms, or data-heavy applications. Explain the unique challenges of designing for these environments.
Demonstrate ICHRA Relevance: If you have direct experience, great. If not, draw parallels to similar complex financial, HR, or operational systems you've designed. Explain how your transferable skills apply.
Visual Clarity: Ensure your slides or digital portfolio are clean, well-organized, and visually appealing. Use high-fidelity mockups and interactive prototypes where appropriate.

📝 Enhancement Note: Interview preparation should focus on demonstrating expertise in complex enterprise design, strong stakeholder management, and a user-centric approach within a regulated industry. Be ready to articulate your process and quantify the impact of your work.

📌 Application Steps

To apply for this Product Designer position:

Submit your application through the Oscar Health careers portal at http://www.hioscar.com/careers/8130858?gh_jid=8130858.
Customize Your Resume: Highlight 4+ years of Product/UX design experience, specifically mentioning complex enterprise software, B2B platforms, or data-intensive applications. Quantify achievements with metrics and tailor keywords to match the job description (e.g., ICHRA, Lucie Marketplace, stakeholder management, Figma, user research).
Curate Your Portfolio: Select 2-3 of your strongest projects that best showcase your experience with complex web/mobile interfaces, enterprise software design, and stakeholder collaboration. Ensure your portfolio clearly articulates your process, role, and the measurable impact of your work. Prepare to present these projects confidently.
Research Oscar Health: Familiarize yourself with Oscar's mission, values, and the Lucie Marketplace. Understand their approach to technology and healthcare. Prepare thoughtful questions about the role, team, and company culture.
Practice Your Presentation: Rehearse your portfolio walkthrough, focusing on clear communication, storytelling, and articulating your design decisions. Be ready to discuss your experience with AI tools and how you approach remote collaboration.

⚠️ 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.

Product Designer, ICHRA