Product Manager, Checkout & Marketplace

Product Manager, Checkout & Marketplace

Truemed helps people take control of their health by unlocking pre-tax HSA/FSA dollars for preventive care. As we scale—connecting hundreds of merchants and millions of consumers—we need to build seamless, compliant, delightful experiences that allow end consumers to shop with their pre-tax HSA/FSA dollars at the intersection of healthcare and payments.

The checkout and marketplace team at Truemed builds the experiences that connect consumers, merchants, and fund administrators. As a Product Manager for this team, you will own the end-to-end experience that allows consumers to spend their tax-advantaged dollars on better health. You'll lead discovery, experimentation, and optimization across Truemed’s e-commerce experiences and funnels , designing and shipping flows that unlock health interventions while maintaining trust, compliance, and merchant satisfaction. You will work closely with engineering, design, and operations to run rapid experiments, analyze conversion data, and build the most delightful checkout experience in health-linked commerce.

We are looking for a product manager who is deeply committed to making healthcare more accessible and preventive. You understand the nuances of checkout conversion, payments, and e-commerce flows. You have a track record of rapid experimentation and shipping winning products. You thrive in fast-moving environments where regulatory complexity meets consumer expectations, and you're obsessed with creating experiences that users trust and love.

What you will do

Own the end-to-end checkout and marketplace experience—including cart flows, payment selection, purchase confirmation, and post-purchase engagement

• Drive a rapid experimentation roadmap—design and run A/B tests, ship learnings fast, and scale winning ideas quickly across the funnel

• Partner with design and engineering to craft simple, high-trust experiences for health + payments use cases

• Build the analytics discipline around checkout performance: define success metrics, instrument funnels, analyze drop-off patterns, and map eligibility conversion

• Serve as the voice of the user in every tradeoff, balancing conversion and UX against compliance, healthcare regulations, and merchant needs

• Champion pace and urgency across the team, modeling decision-making speed and outcome ownership

• Demonstrate ability to make technical tradeoff decisions, working across legal, operations, engineering, and design to build state-of-the-art commerce experiences

• Navigate and prioritize amidst rapidly changing product specs, flexing into different domains (payments, compliance, marketplace dynamics) to bring clarity and execute

• Exercise judgment and decision-making in ambiguous situations—especially at the intersection of healthcare regulation, consumer trust, and merchant economics

• Think creatively about the risks and benefits of enabling HSA/FSA spend in new categories, moving beyond past playbooks to unlock new health interventions

Who you are

• 4–6 years in Product Management, focused on checkout, payments, or e-commerce flows

• Domain expert in funnel conversion and cart/checkout UX optimization

• AI-fluent: has experience using LLMs to improve team velocity and deliver value to users faster

• Highly autonomous: thrives with minimal oversight, proactively identify problems and ship solutions without waiting for direction

• Bias for action: moves from idea to experiment to shipped product in days, not weeks.

• Champion of end users: deeply understands consumer purchase behavior and excels at synthesizing user research into actionable insights

• Growth mindset: Innately curious and eager to learn, with a proven record of implementing learnings iteratively in product and process.

• Detail-oriented: has exceptional taste for checkout experiences (copy, latency, trust cues)

• Analytical rigor: comfortable with funnel analysis, experiment design, and A/B testing

• Based in San Francisco, Los Angeles, Austin, or New York

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. We do this by supporting these 5 habits that research shows are tied to significantly improved health outcomes:

1. Eating healthy food

2. Getting an adequate quantity and quality of sleep

3. Increasing movement and exercise and reducing sedentary behavior

4. Reducing chronic stress

5. Increasing sunlight and minimizing environmental toxins

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. By allowing consumers to spend these pre-tax dollars on goods that make them healthier, we'll incentivize consumers to invest in their health and begin to reverse the explosion in chronic illness that's plagued the US for the last 50 years.

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

• Coworking stipend

• L&D Stipend

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