Founding Software Engineer

About DearBill
Americans lose billions every year to healthcare bills they shouldn't have to pay — overcharges, missed savings programs, and enrollment processes so broken that people simply give up. DearBill exists to fix that. Our mission is simple and ambitious: save consumers money so they can live longer and spend more.

We're building the consumer financial platform for healthcare — one that people trust the way they trust their bank. That means automating the painful stuff (like enrolling patients in Medicare prescription payment programs without a single phone call), integrating directly with providers and health systems, and eventually rewarding people for every dollar we put back in their pockets.

The Role

As our Founding Engineer, you'll build the technical foundation of DearBill alongside the founders. This isn't a "maintain the system" job — it's a "there is no system yet, come invent it" job. You'll ship the automation, integrations, and consumer experiences that turn a byzantine healthcare billing process into something that just works.

Healthcare is one of the hardest industries to build in — legacy portals, faxes, phone trees, HIPAA, and regulatory landmines everywhere. That's exactly why the opportunity is so big, and why we need an engineer who sees hard-to-automate workflows as a challenge, not a blocker.

What You'll Do

• Build enrollment automation end to end: RPA agents that navigate payer and pharmacy portals, AI voice agents for phone-based fallbacks, and the orchestration layer that decides which path to take
• Design and ship secure integrations with provider EHRs and partner systems (HIPAA-compliant APIs, secure data handoffs, real-time status syncing)
• Build the consumer-facing product: enrollment status, savings tracking, notifications, and eventually the rewards platform
• Own reliability in a world of flaky third-party systems — retries, fallbacks, human-escalation paths, and monitoring that catches problems before patients feel them
• Make foundational architecture decisions with compliance in mind from day one (HIPAA, data security, auditability)
• Work directly with the founders, partners, and early customers to figure out what to build next — then build it that week

What We're Looking For

• 5+ years of software engineering experience, with real ownership of production systems
• Strong full-stack generalist: comfortable across backend services, integrations, and consumer-facing frontend
• Experience with automation of messy real-world workflows — RPA, browser automation, LLM/AI agents, or scraping hostile legacy systems
• Comfort building in regulated environments, or the judgment and humility to learn fast (HIPAA experience is a big plus)
• Bias toward shipping: you'd rather get a working fallback into production today than a perfect abstraction next quarter
• Genuine motivation for the mission — you want your work to measurably reduce what real people pay for healthcare

Nice to Have

• Prior experience as an early engineer (first 1–10) at a startup
• Healthcare or fintech background: EHR integrations (FHIR/HL7), payer systems, Medicare/Part D, payments, or banking infrastructure
• Experience with AI voice agents, LLM-powered workflows, or document/bill parsing
• Familiarity with SOC 2 / HIPAA compliance tooling and practices

What We Offer

• Meaningful founding-level equity & Competitive Salary Package
• A direct seat at the table on product, architecture, and company strategy
• A mission you can explain to your family in one sentence — and be proud of