Product Management Jobs 2026 (Now Hiring) – Smart Auto Apply

The Role

Truemed helps people take control of their health by unlocking pre-tax HSA/FSA dollars for preventive care. We are the payments infrastructure that connects health and wellness merchants to billions of dollars in tax-advantaged consumer spending — powering seamless HSA/FSA transactions at checkout across Shopify storefronts, direct integrations, and emerging platforms.

Design at Truemed spans four product surfaces: the consumer checkout and qualification flow, the merchant platform and dashboards, the Truemed marketplace, and tooling for Clinical Providers. As Product Designer, you will be responsible for the end-to-end experience across all of these surfaces alongside our design engineer. You will partner directly with PMs, engineers, marketing, and analytics team members to interview users, define problems, explore solutions, prototype rapidly, and ship product improvements that move conversion, merchant NPS, and consumer trust.

We are looking for a designer who has a passion for health and wellness. You treat AI as a core tool, not a novelty. Your workflow starts in an LLM — clarifying intent, drafting flows, surfacing edge cases — and moves into prototyping tools like Cursor or Claude Code before landing in Figma for system-level polish. You are fast because you are leveraged, not because you cut corners. You have strong opinions about interaction design and visual craft, but you hold them loosely when data or user research says otherwise.

This is not a role where you receive specs and make them pretty. You will research and understand what users care about, shape what gets built, care intently how it works, and evangelize why the details matter. If you want to own the design function at a company whose product directly changes how people spend on their health, this is the job.

What you will do

• Own design end to end for projects that span all product surfaces: consumer checkout and qualification, merchant platform, marketplace, and internal tools — from problem definition through launch and iteration

• Start work in an LLM: use Claude to clarify user problems, draft interaction flows, surface edge cases, and align quickly with PM and engineering before touching pixels

• Prototype using AI tools: use Cursor, Claude Code, or similar to build and iterate on flows and lightweight interfaces — letting AI generate code while you guide structure, behavior, and UX quality

• Partner with PMs to define strategy, goals, experiments and success metrics for every initiative and use results to adjust direction

• Run self-serve research to validate assumptions: friction logs, quick usability tests, merchant interviews, session replays. Leverage research as a velocity tool, not a gate

• Bring work into Figma for full state coverage, component architecture, and production-ready handoff — building the foundations of Truemed's design system as you go

• Design for the 80/20: encode judgment and complexity under the hood while keeping default experiences simple, trustworthy, and high-converting

• Shape the design culture: establish critique rhythms, share prompts and patterns, and set the craft bar for the team as design grows

Who you are

• Builder and designer: 4–6 years designing complex products, ideally in B2B, fintech, payments, or health tech. You've shipped end-to-end, not just explorations but product that moved a metric. You can point to work where your design directly changed a business outcome.

• Product-minded: You define problems before solving them. You can articulate why something should be built, not just how it should look. You've partnered with PMs and engineers to set scope, cut features, and ship the version that matters.

• AI-native: You use LLMs daily to draft flows, write microcopy, explore edge cases, generate prototypes. You've used Cursor, Claude Code, Replit, or similar to build working interfaces yourself. You think about AI as a design material, not just a productivity hack.

• Systems thinker: You see patterns across surfaces and build for reuse. You've contributed to or built design systems — component libraries, token structures, interaction patterns — and you understand when to standardize and when to deviate.

• Interaction design craft: You have exceptional taste for how interfaces feel — transitions, states, loading, error handling, microcopy. Your checkout flows don't just convert; they build trust.

• Bias for action: You default to shipping and learning. You've designed and shipped a meaningful v0 in under two weeks and know what it takes to do it again. You don't wait for perfect inputs.

• Clear communicator: You present design decisions with conviction and rationale. You give and receive critique well. You write clearly — in specs, in Slack, in async updates.

Bonus (not required)

• Experience in payments, fintech, or healthcare (checkout flows, compliance-adjacent UX, trust-critical interfaces)

• Experience as the first or early designer at a startup — building process and culture, not just shipping features

• Familiarity with experimentation frameworks and designing for A/B tests (variant isolation, metric instrumentation)

• Experience with Shopify ecosystem, e-commerce platforms, or multi-sided marketplace design

About Truemed

Our mission is to reverse chronic illness back to 1970s levels and make Americans healthy again. We will do this by shifting hundreds of billions of dollars away from our current broken healthcare system, and towards effective lifestyle interventions and prevention. Today's healthcare system spends less than 3% of the $4.3T in annual spending on prevention. This has to change.

Today, 95% of all medical costs go to treating illness. Our goal is to empower people to invest in healthy habits today rather than treating illness in the future. Truemed enables patients to use pretax HSA/FSA funds to buy healthy food, exercise equipment, and supplements. We support brands like Peloton, Eight Sleep, Momentous, and hundreds of others. We're building the infrastructure that allows health and wellness merchants to accept the $150+ billion tied up in HSA and FSA accounts.

Comp and benefits

• Comp and equity in the top decile for Series A startups

• Comprehensive medical, dental, and vision insurance with employer sponsored HSA contributions

• 401(k)

• Unlimited PTO

• Based in San Francisco, Los Angeles, or Austin

• Coworking stipend

• L&D Stipend

• 2x/year company offsites and 2x/year team offsite