Founding Product Designer

**About DearBill
DearBill puts money back in retirees' pockets. We build an agentic AI platform that finds, applies for, and manages medication affordability programs for people on Medicare. Half of Medicare members live on tight budgets, and tens of billions of dollars in help goes unclaimed every year because the paperwork is brutal.
Our agent does the paperwork. It screens a member against programs like the Medicare Prescription Payment Program, Extra Help, and state pharmaceutical assistance programs, submits the applications (e-signature, fax, and insurer follow-up included), and tracks every case to approval and reverification. It's free for members. The long-term vision is an impartial AI agent for every Medicare consumer: prescriptions first, then every healthcare bill.
**The role
You will be the designer who makes an AI agent feel trustworthy to a 72-year-old who has never used one. DearBill has three surfaces, and you own the experience across all of them:
Member experience — the consumer product: onboarding, program screening, consent and e-signature, and case status that a member (or their adult child) can understand in one glance.
Partner experience — the tools that pharmacists, care managers, and counselors use to refer patients and see where each case stands.
The agent itself — how an AI that fills forms, sends faxes, and chases insurers explains what it's doing, asks for what it needs, and earns trust at every step.
This is an early, hands-on role on a small team. You'll work directly with the founder and the engineers, ship weekly, and talk to members and partners yourself. You will set the design standards the company grows into.
**What you'll do
Own end-to-end UX and UI for the member app, the partner tools, and the agent's conversational flows, from problem framing to shipped pixels.
Design for older adults and their caregivers: large type, plain language, low cognitive load, accessible by default (WCAG 2.2 AA as the floor, not the ceiling).
Turn complicated government programs into simple decisions. Eligibility rules, consent, reverification dates, and plan cost-sharing all need to be legible without being dumbed down.
Design the agent's voice and behavior: status updates, requests for documents, explanations of what happened and what's next, and graceful handling of delays and denials.
Run lightweight research: member calls, partner shadowing at pharmacies and clinics, usability sessions, and support-ticket review. Bring what you learn back as design changes.
Build and maintain the design system in Figma and partner with engineers so it lands in code cleanly.
Write member-facing copy with the product and compliance leads; words are half the interface here.
Design partner-facing materials and marketing pages when they touch the product story (referral flows, onboarding guides, the providers and pharmacy pages).
Prototype fast, test with real people, and ship weekly with the engineering team.
**Who you are
4+ years designing shipped consumer or healthcare products, with a portfolio that shows the thinking behind the screens, not just the screens.
Strong in both UX and visual design. You can run a research session in the morning and polish a component library in the afternoon.
You've designed for people who are not like you: older adults, people in financial stress, low digital literacy, or a clinical workforce. You know what it takes to make something feel safe.
You write well. Clear, warm, plain English is a core skill for this job.
You're comfortable with ambiguity and ownership. You will often be the only designer in the room and the person deciding what "done" looks like.
Fluent in Figma, prototyping, and working inside an engineering sprint process (we use Linear).
You care about this problem. People choosing between medication and groceries is a thing that happens every day in this country, and you want to fix it.
**Nice to have
Experience designing conversational or agentic AI products, especially ones that take actions on a user's behalf.
Familiarity in Medicare, pharmacy, benefits enrollment, fintech, or government services.
Familiarity with accessibility testing tools and assistive tech (screen readers, magnification, voice control).
Enough front-end skill (HTML/CSS, React, or Tailwind) to prototype in code or tune implementation details with engineers.
Spanish or another language common among Medicare members.
**How we work, and the details
Location: New York City. We work from our Tribeca office and prefer candidates who can be in-person most of the week; hybrid is possible for the right person.
Team: founder, three engineers, founding operations leader, and advisors. You'd be the first dedicated design hire reporting into fractional CMO
Employment type: Full-time / contract-to-hire
Compensation: 75K plus meaningful early-stage equity. Health benefits included.
Interview process: intro call → portfolio review → a short take-home or live design exercise built on a real DearBill problem → meet the team. We move in under two weeks.
To apply: send a portfolio and a few lines on a product you've designed for someone very different from yourself to [email protected].
DearBill (Healthcare Payments Partners, Inc., d/b/a Dearbill) is an equal opportunity employer. We welcome applicants of every background, age, and ability — the members we serve are all of those things.

Skills
React, HTML/CSS, Figma, Prototyping, Onboarding

Experience
4+ yrs

Work arrangement
No