Senior Product Designer

Pivotal Health•New York, NY

8d•$145,000 - $170,000•Hybrid

About The Position

Pivotal Health is hiring a Senior Product Designer to shape the look, feel, and functionality of its products. Reporting to the Founding Product Designer, this person will own significant product areas from discovery through launch, creating clear and intuitive interactions and thoughtful visual design for complex healthcare workflows. The designer will work closely with Product Managers and Engineers on customer-facing portals and internal tools. The role involves understanding user needs, exploring solutions, prototyping, gathering feedback, and ensuring the quality of shipped experiences. As the platform develops AI-powered and agentic workflows, the designer will help make those experiences understandable and useful. This is a hands-on role with substantial ownership on an early design team, requiring strong product judgment, design craft, independence in ambiguous situations, and practical decision-making. Pivotal Health combines software, data, and services in an AI-driven platform that helps healthcare providers dispute underpaid claims and recover reimbursement while reducing administrative work. Its full-service Independent Dispute Resolution solution is the starting point for broader tools supporting providers across the reimbursement journey. The role follows the company’s New York City hybrid model, with in-person collaboration expected. Candidates must be authorized to work in the United States without current or future employer sponsorship. Employment is at-will and contingent upon successful completion of applicable background checks, where permitted by law.

Requirements

5–8 years of product design experience, including substantial work on complex B2B software, fintech, financial, or accounting products.
Experience owning a product line or significant product area and working directly with Product Managers and Engineers throughout the development lifecycle.
A portfolio demonstrating strong product thinking, visual craft, shipped outcomes, and clear explanations of design decisions and tradeoffs.
Ability to translate complex workflows, information, and business requirements into intuitive user experiences.
High proficiency in Figma, including prototyping, components, and design systems.
Effective use of AI tools such as Claude or ChatGPT, and ability to incorporate tools such as Cursor or Codex into prototyping and product development workflows.
Ability to independently conduct focused user research and translate findings into concrete design decisions.
Initiative to identify problems and move work forward without waiting for perfectly defined requirements.
Clear communication, openness to feedback, and flexible collaboration, including knowing when to advocate for a design decision and when to compromise.
Willingness and excitement to collaborate in person with teammates through the New York City hybrid model.
Authorization to work in the United States without current or future employer sponsorship.

Nice To Haves

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 helping users understand, guide, and review automated work.

Responsibilities

Lead design for significant product initiatives from problem definition and research through prototyping, delivery, and iteration, including production edge cases and interaction details.
Partner with Product Managers and Engineers early to shape requirements, explore options, assess feasibility, make tradeoffs, and consider platform-wide impacts.
Translate complex processes, data, and business rules into clear, intuitive experiences across customer-facing portals and internal tools.
Improve visual craft and product quality through attention to hierarchy, layout, typography, interaction patterns, and UI states; stay involved through implementation and design QA.
Independently plan and conduct focused user research, customer conversations, and usability testing; use prototypes to gather feedback, validate assumptions, and refine solutions.
Evolve the design system by reusing and improving existing components and patterns or introducing new approaches, balancing consistency with workflow needs.
Incorporate AI tools into exploration, prototyping, and everyday problem-solving, using judgment to evaluate outputs and inform product decisions.