Senior Product Designer

About Pivotal Health Pivotal Health is the leading technology platform that helps healthcare providers get paid fairly in an increasingly complex reimbursement landscape. Today, many providers face persistent underpayment from health insurance companies, despite delivering high-quality care. While processes like IDR (Independent Dispute Resolution) were designed to promote fairness, they’re often administrative-heavy, time-consuming, and difficult to navigate without the right tools. Pivotal Health combines software, data, and service into a seamlessly integrated, AI-driven platform that simplifies these complex reimbursement workflows. We help providers efficiently dispute underpaid claims, reduce administrative burden, and recover the reimbursement they’re entitled to; without adding more work to already stretched teams. Our full-service IDR solution is just the starting point. We’re building solutions that enable providers to operate with clarity, control, and confidence across the reimbursement journey. About the Role We’re hiring a Senior Product Designer to help shape how Pivotal’s products look, feel, and work. Reporting to our Founding Product Designer, you’ll own meaningful product areas from discovery through launch, bringing clarity, intuitive interactions, and thoughtful visual design to complex healthcare workflows.

You’ll partner closely with Product Managers and Engineers across customer-facing portals and internal tools. Your work will span understanding user needs, exploring solutions, building prototypes, gathering feedback, and ensuring the shipped experience meets a high bar for quality. As our product evolves to incorporate more AI-powered and agentic workflows, you’ll help make those experiences understandable and useful.

This is a hands-on role for someone who combines strong product judgment with excellent design craft. You should be comfortable navigating complex B2B software, working independently through ambiguity, and making practical tradeoffs without losing sight of the details. You’ll join an early design team with substantial ownership and the opportunity to strengthen both our product experiences and the design foundations behind them.

What You’ll Do

• Own End-to-End Product Design: Lead design for significant product initiatives, from problem definition and research through prototyping, delivery, and iteration. Take responsibility for how the experience works in production, including edge cases and interaction details.

• Partner Closely with Product and Engineering: Work alongside PMs and Engineers early in the development process to shape requirements, explore options, assess feasibility, and make thoughtful tradeoffs. Connect decisions within your product area to their impact across Pivotal’s platform.

• Simplify Complex Workflows: Turn intricate processes, data, and business rules into clear, intuitive experiences across customer-facing portals and internal tools.

• Elevate Visual Craft and Product Quality: Bring care to hierarchy, layout, typography, interaction patterns, and UI states. Stay involved through implementation and design QA to ensure the shipped product reflects the intended experience.

• Conduct Practical User Research: Independently plan and run focused research, customer conversations, and usability testing. Use prototypes to gather feedback, validate assumptions, and refine solutions without relying on a dedicated research team.

• Evolve Our Design System: Build on existing components and patterns, identifying where to reuse, improve, or introduce new approaches. Understand how changes affect other experiences and balance consistency with the needs of each workflow.

• Use AI to Improve Your Process: Incorporate AI tools into exploration, prototyping, and everyday problem-solving. Apply your judgment to evaluate outputs and turn faster iteration into better product decisions.

Who You Are

• You bring 5–8 years of product design experience, including substantial work on complex B2B software, fintech, financial, or accounting products.

• You’ve owned a product line or significant product area and worked directly with Product Managers and Engineers throughout the development lifecycle.

• You have a portfolio that demonstrates strong product thinking, visual craft, and shipped outcomes, with clear explanations of your decisions and tradeoffs.

• You’re skilled at translating complex workflows, information, and business requirements into intuitive user experiences.

• You’re highly proficient in Figma, including prototyping, components, and design systems.

• You use AI tools such as Claude or ChatGPT effectively and can incorporate tools such as Cursor or Codex into prototyping and product development workflows.

• You can independently conduct focused user research and translate what you learn into concrete design decisions.

• You take initiative, identify problems, and move work forward without waiting for perfectly defined requirements.

• You communicate clearly, welcome feedback, and collaborate with flexibility. You know when to advocate for a design decision and when to make a practical compromise.

• You’re excited to collaborate in person with teammates through our New York City hybrid model.

Extra Credit if you have:

• Experience as an early design hire or on a small design team at a growing startup.

• Background designing financial, accounting, or similarly complex products with detailed workflows and interconnected data.

• Experience designing for healthcare or another regulated industry.

• Experience building and maintaining design systems used across multiple product areas.

• Experience designing AI-powered or agentic experiences, including how users understand, guide, and review automated work.

Why You’ll Love Working Here We’re a collaborative, low-ego team on a mission to make healthcare reimbursement fairer for providers. While we primarily hire around our core hubs–Los Angeles and New York–we remain open to exceptional talent outside those regions. Remote and hybrid flexibility varies by role and team, and is outlined in each job description. If you’re excited by solving complex problems and making a real-world impact, we’d love to hear from you. Benefits Include:

• Competitive compensation, including equity

• Full health, dental, and vision coverage

• Retirement savings plan through 401(k)

• Flexible time off

• Opportunities for company-wide connection and events

Ready to Make an Impact? We’re building something meaningful; and we want you on the team. Bring your ideas, curiosity, and drive, and let’s transform healthcare reimbursement together.

Employment Information Work Authorization Candidates must be authorized to work in the United States without current or future employer sponsorship. Equal Employment Opportunity Pivotal Health is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, color, religion, sex, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected status. Reasonable Accommodations Pivotal Health provides reasonable accommodations for qualified individuals with disabilities in accordance with applicable laws. If you need assistance during the application or interview process, please let us know. Background Checks Employment is contingent upon successful completion of applicable background checks, where permitted by law. At-Will Employment Employment with Pivotal Health is at-will and may be terminated by either party at any time, with or without cause or notice, in accordance with applicable law.