Founding Product Designer

Pivotal Health•Los Angeles, CA

About The Position

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 As Pivotal’s founding Product Designer, you’ll own how our product looks, feels, and works as it evolves over time. You’ll establish the foundational design systems, patterns and core user flows that will serve as the backbone of the product as we scale. Partnering closely with Product Managers and Engineering leads, you’ll bring design ownership to the product triad and ensure design decisions translate into cohesive, scalable outcomes across the platform. Pivotal has built meaningful traction at the intersection of healthcare services and technology. Much of our design work to date has been pragmatic and AI-assisted, enabling speed and early progress, but we’re ready to level up. This role is product-heavy and execution-focused, centered on bringing clarity, consistency, and intuition to complex workflows, owning end-to-end product design strategy, and establishing foundations that scale with the business. This is a hands-on builder role for someone excited to turn emerging patterns into a strong, scalable design foundation. If you thrive in ambiguity, enjoy shaping both vision and execution, and want to elevate how an existing product is designed and experienced, this role offers the chance to have outsized impact alongside thoughtful Product and Engineering partners.

Requirements

5+ years of experience in product design, ideally in B2B, SaaS, or complex product environments.
Strong product instincts — you think holistically about problems, not just screens.
Experience owning end-to-end design for meaningful product areas.
Comfort working in ambiguity and making progress without perfect inputs.
Ability to balance speed, quality, and pragmatism in an early-stage environment.
Strong communication skills — you can explain your thinking and invite productive debate.
Enjoy collaborating closely with Product and Engineering teams.

Nice To Haves

Experience as a first or early design hire.
Awareness of existing brand guidelines and comfort aligning product UI accordingly, with occasional coordination across teams as needed.
Background in regulated, technical, or workflow-heavy domains (healthcare, fintech, govtech, etc.).
Comfort leading user research or usability testing.
Experience building and iterating on design systems in fast-moving environments, balancing speed, consistency, and long-term scalability.

Responsibilities

Product Partnership & Strategy: Partner deeply with Product Managers and Engineering leaders to shape product direction and ensure design decisions translate into cohesive, scalable product experiences over time.
End-to-End Product Design: Own design from concept through shipped product, taking ambiguous problems and turning them into intuitive, well-executed workflows rather than vision-only concepts.
Systems & Foundations: Establish and evolve design patterns, components, and guardrails that bring consistency across the product while supporting fast iteration and long-term scale.
Design–Engineering Alignment: Create clear, intentional design direction that reduces iteration churn with front-end engineering and ensures what’s built reflects thoughtful, deliberate UI decisions.
Customer Insight & Pragmatic Research: Use lightweight research, customer feedback, and emerging usage data to inform design decisions, especially where workflows and behavior are still being discovered.