Senior Software Engineer – Checkout Team

Location: Remote – United States
Company Stage of Funding: Series A – $44M Raised
Office Type: Fully Remote
Salary: $175,000–$225,000 + Competitive Equity

Company Description

We’re representing a fast-growing healthcare fintech company redefining how consumers use HSA and FSA dollars for preventive health and wellness products. The platform integrates directly into merchant checkout experiences, allowing customers to use pre-tax healthcare funds for eligible products from leading brands across fitness, recovery, sleep, wearables, and wellness.

The company partners with major consumer brands including Peloton, Garmin, and Sleep Number and is building infrastructure that connects more than $150B in pre-tax healthcare spending to products that improve health outcomes.

Backed by Andreessen Horowitz and Bessemer Venture Partners, the company has raised approximately $44M and maintains a deliberately small engineering organization where senior engineers own major product areas end-to-end.

What You Will Do

• Own large, consumer-facing checkout features from initial product definition through production launch.
• Build polished purchase experiences using Next.js, React, and TypeScript.
• Work primarily on frontend systems while remaining capable of making meaningful backend changes in Python and Django.
• Design and improve checkout flows that optimize conversion, usability, reliability, and customer experience.
• Work directly with backend models, APIs, and data structures when product initiatives require full-stack ownership.
• Collaborate closely with Product, Design, and Marketing to define the direction of the checkout experience.
• Improve page load performance, rendering behavior, and Core Web Vitals.
• Help establish frontend architecture, engineering patterns, and standards across the team.
• Expand backend systems and data models required to support new checkout capabilities.
• Own features end-to-end rather than handing work between frontend and backend specialists.
• Use modern development tools, including AI-assisted coding workflows, as part of normal engineering execution.
• Debug complex production issues and continuously improve the reliability of revenue-critical checkout systems.

Ideal Background

• 3–7+ years of professional software engineering experience, with clear progression toward senior-level ownership.
• Strong frontend engineering depth with React, Next.js, and TypeScript.
• Proven experience building consumer-facing checkout, payments, e-commerce, or purchase flows.
• Full-stack enough to independently navigate and modify backend systems written in Python/Django.
• Strong understanding of web fundamentals beyond framework-level React development.
• Comfortable reasoning about browser behavior, rendering, performance, APIs, and data flow across the stack.
• Solid database fundamentals, including data modeling and writing efficient queries.
• Proven ability to own large product features from inception through deployment.
• Strong communicator and collaborative teammate.
• Track record of increasing technical responsibility and meaningful ownership.
• Comfortable working autonomously within a small, distributed engineering organization.
• Based in the United States.

Preferred

• Experience at a company known for a world-class consumer checkout experience, such as Shopify, Target, Walmart, Amazon, Instacart, DoorDash, Etsy, Wayfair, or similar.
• Background at consumer fintech or payments companies such as Stripe, Square, Affirm, Chime, Klarna, Afterpay, Brex, Plaid, or Cash App.
• Experience within consumer health or wellness companies such as Hims & Hers, Ro, Noom, WHOOP, Headspace, or similar.
• Hands-on experience improving web performance, page load times, and Core Web Vitals.
• Payments infrastructure experience.
• Experience building revenue-critical consumer products at meaningful scale.
• Strong understanding of backend systems without being exclusively backend- or infrastructure-focused.
• Genuine interest in preventive health and expanding consumer access to HSA/FSA funds.

Candidates who describe themselves primarily as frontend developers and avoid backend ownership are unlikely to be a fit. The team is specifically looking for engineers who combine deep frontend expertise with enough full-stack capability to independently ship an entire checkout feature.

Compensation and Benefits

• Base salary: $175,000–$225,000.
• Competitive equity package.
• Potential $10,000 signing bonus for exceptional candidates.
• Fully remote anywhere in the United States, including Alaska and Hawaii.
• No U.S. timezone restrictions.
• H-1B transfers and certain existing visa transfers can be considered; new sponsorship is not available.
• Two planned hires for the Checkout team.
• Modern stack including Next.js, React, TypeScript, Python, Django, and Tailwind.
• Comprehensive medical, dental, and vision benefits.
• Employer HSA contributions.
• 401(k).
• Unlimited PTO.
• Coworking and learning-and-development stipends.
• Quarterly team offsites.
• Interview process includes a 30-minute introductory conversation, practical live coding exercise, feature/system design interview, behavioral interview, culture interview, and CEO conversation.
• Best suited for senior engineers who want to own high-impact consumer checkout experiences end-to-end rather than operate within a narrowly defined frontend specialty.