Founding Engineer — Overdrive Health (YC W26)

New York City (In-Person) · Full-Time

About Overdrive Health

Medical billing is a $150B+ industry still run almost entirely by people doing manual administrative work: logging into payer portals, looking up codes, writing appeals, making phone calls. There are over 7,000 billing companies in the US, and 80% of their costs are human labor that AI can now automate.

Rather than selling software to an industry that's slow to adopt it, we acquire billing companies and deploy AI directly into their operations. We automate insurance phone calls, document processing, benefit verification, claim coding, denial management, and more. We capture 100% of the value we create, and every acquisition expands our client base, our data, and our ability to automate.

We started in ambulance billing ($2B market). Our first billing company serves 25 ambulance agencies and is on pace to collect $60M this year. In four months, we've increased revenue per employee by 1.7x and eliminated 75% of the offshore team through automation. We have a ton left to build just to get this first billing company to a true AI-native business, and then we'll expand into other verticals.

The Founder

Overdrive is led by Michael Schroeder, who led core AI engineering at EliseAI (scaled from $35M to $115M ARR; $250M Series E led by a16z) and led engineering at Up&Up, a full-stack property manager ($30M Series B from Khosla and Founders Fund). Before that: Citadel, Meta, Duke CS.

The Role

You'd be the first engineering hire, working directly with Michael to build and expand the AI systems that power our billing operations. This is not a research role. Our agents are already in production handling real claims and real money. You'll be shipping code that has a direct, measurable impact on revenue from day one.

The work is varied. One week you're building an AI agent that navigates a payer's phone tree to verify benefits. The next you're designing the data pipeline that routes thousands of claims through the right automation workflows. Then you're building an internal tool so our billing team can review agent outputs and flag edge cases. You should be the kind of engineer who's more excited about solving a gnarly integration problem with a payer API than picking a frontend framework.

This is a true ownership role. You won't just write code. You'll make foundational architectural decisions, shape the product roadmap based on what you see in the data, and help build the engineering team and culture from scratch.

What You'll Do

• Build and iterate on AI agents that automate core billing workflows (insurance phone calls, claim follow-ups, denial appeals, benefit verification, document extraction)
• Design and maintain backend systems, data pipelines, and integrations with healthcare and insurance infrastructure (payer portals, clearinghouses, EHR/ePCR systems)
• Make foundational architectural decisions that will scale as we expand into new medical billing verticals
• Build internal tooling to support our operations team and close the feedback loop between human billers and AI agents
• Work directly with our billing team to understand where automation creates the most leverage, then ship solutions quickly

What We're Looking For

• Strong backend engineering fundamentals. You're comfortable designing systems, writing reliable production code, and debugging hairy problems across the stack.
• Experience building with LLMs or AI agents. You've put something into production, not just prototyped in a notebook.
• Bias toward shipping. We're a small team with a fast feedback loop; you care more about solving the problem than perfecting the abstraction.
• High agency. You'll often be deciding what to build, not just how to build it.
• You've built entire systems yourself, don't need detailed specs or product managers, and take full ownership over your projects.
• Python proficiency (our stack is Python-heavy).

Nice to Have

• Experience in healthcare, billing, insurance, or other heavily regulated industries
• Background working with telephony systems (Twilio, SIP), document processing, or workflow automation
• Previous early-stage startup experience
• You use tools like Cursor and Claude Code effectively, and can write good code without them

Why Overdrive

• Real business, real traction. We're on pace to collect $60M in claims this year across 17 ambulance providers, with AI agents already in production. Your code will move real money starting on day one.
• Massive market. Ambulance billing is our starting point. The broader medical billing market is $100B+, and the underlying automation infrastructure is shared across specialties.
• Founder who's done it before. Michael has scaled AI systems in operationally complex industries from early stage through $100M+ ARR.
• Foundational role. You'd be the first engineer. You'll have meaningful input on architecture, hiring, product direction, and company culture.