Sr. Product Designer

About Thoughtful

Thoughtful is building AI Agents that automate the most expensive, repetitive, and error-prone workflows in healthcare—starting with revenue cycle management. Our agents work across claims, billing, prior authorizations, denials, and more to help providers get paid faster with fewer administrative headaches.

Behind every great agent is a great interface. We're not just building dashboards—we’re designing a new way for humans to collaborate with intelligent systems.

The Opportunity

We're looking for a Product Designer to lead the UX and UI design of our platform, helping users interact fluidly with AI agents across a range of healthcare workflows. This role sits at the intersection of user needs, agent behavior, and system transparency. You’ll partner with product, engineering, and leadership to create design systems and product surfaces that are intuitive, powerful, and delightful.

You’ll have ownership of the end-to-end design process—from concept through craft—and play a pivotal role in defining how people engage with autonomous work.

What You’ll Do

• Design core interfaces that allow users to deploy, monitor, and collaborate with AI agents.
• Shape the design system that supports both customer-facing and internal tooling experiences.
• Translate complex workflows into simple, elegant UI/UX patterns that drive adoption and trust.
• Lead design explorations across low-fidelity concepts and high-fidelity prototypes with speed and polish.
• Partner closely with engineers to ship high-quality, pixel-perfect interfaces.
• Bring a strategic mindset to prioritization, design tradeoffs, and iterative testing.
• Act as a champion of the user—identifying pain points, gathering feedback, and evolving the product experience over time.
• Regularly share work with stakeholders and incorporate input to move quickly without compromising quality.

What We’re Looking For

• 5+ years of product design experience at fast-paced software or AI companies.
• A strong design portfolio that demonstrates your ability to craft interfaces that are both functional and beautiful.
• Comfort working across the full product lifecycle—from zero-to-one bets to system-level iteration.
• Proven ability to distill complex systems into intuitive user flows and components.
• Systems thinker who loves creating shared patterns and scalable design frameworks.
• Bias toward action with a love of rapid iteration, feedback loops, and continuous learning.
• Excellent communicator with strong opinions, loosely held—you can present and defend your decisions with clarity and grace.
• Experience designing for technical users (bonus: platform, B2B, or developer tools).

You’ll Thrive Here If You...

• Want to shape the future of human-AI collaboration—not just design another dashboard.
• Sweat the details and are obsessed with polish, hierarchy, and usability.
• Enjoy working directly with founders, engineers, and customers in fast feedback cycles.
• Love turning ambiguity into structure and forward momentum.
• Have a high bar for craft and aren’t afraid to own big problems end-to-end.

Why Thoughtful?

• Competitive compensation with significant performance-based incentives
• Employee stock options—we win together
• Full medical, dental, and vision coverage
• Minimum three weeks PTO—we expect you to rest, recharge, and return inspired

California Salary Range

$140,000—$190,000 USD