💡 Mission
The U.S. healthcare system is a mess—confusing, error-prone, and financially devastating. Medbill AI is on a mission to fix that.
We’re building the go-to platform for Americans to navigate insurance, fix medical bills, and fight back against broken systems—with the help of AI, great design, and human advocates. We make it easier to understand coverage, challenge denials, and save money. Our goal is to become the #1 platform that helps people take control of their healthcare.
🩺 About Us
Founded by Oscar Health veterans, we’re a seed-stage company backed by $17M from Forerunner, RRE, and the founders of Hugging Face, Truebill, Rocket Money, and more. We’re a team of 18 (and growing), based in NYC, building fast and solving real problems for real people.
🚀 About the Role
We’re looking for a Strategy & Operations Lead to help us define and drive how Medbill AI grows. This role is equal parts business strategy, go-to-market, and scrappy execution.
You’ll lead market research, explore new distribution channels (B2B2C), evaluate and run partnerships, and turn fuzzy ideas into crisp execution plans. You’ll sit at the center of product, operations, and leadership—bringing structure to ambiguity and clarity to complex opportunities.
This is a hybrid role based in NYC (3–4 days/week in-office).
💼 What You’ll Own
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Market Discovery & Distribution Strategy
Identify high-potential channels and audiences. Size the opportunity, run experiments, and guide GTM focus areas.
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Partnership Development
Build and manage a pipeline of B2B2C opportunities—employers, providers, payers, brokers, nonprofits, and other potential partners. Own early conversations and execution.
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Regulation & Competitive Research
Track how the landscape is shifting, from AI applications in healthcare to regulatory changes and new entrants. Turn insight into strategy.
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Special Projects
Launch new initiatives, product extensions, or internal systems. If it's ambiguous but important, it's probably yours.
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Internal Infrastructure
Stand up lightweight tooling for CRM, outbound, and BD processes. Work across teams to keep us aligned and moving fast.
🎯 You Might Be a Fit If You...
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Have 4–6+ years of experience in consulting, corporate strategy, investing, or an early-stage startup in a strategy/ops role
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Are fluent in market sizing, business modeling, competitor mapping, and the “zero to one” discovery process
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Have worked directly with founders or executive teams on key business decisions
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Are energized by owning a problem end to end—scoping it, testing it, and scaling it
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Think in frameworks but operate with urgency
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Are curious about AI, healthcare policy, and fixing broken systems
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Have strong communication and collaboration skills—your writing is sharp, your decks are tighter, and people trust your instincts
🌟 Bonus if you...
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Have experience in digital health, revenue cycle, benefits, or health insurance
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Have an MBA or equivalent experience managing strategic growth bets
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Are a strong operator who knows how to set up systems that scale
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Care deeply about solving real-world problems for real people
🦸 Working with Us
Medbill AI is based in New York. Our team is split evenly between our Chelsea office & the US. We marry the best of in-office culture with the best of a remote-first company.
We’re a team of passionate individuals who show up every day to do the best work of their lives following these principles:
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Move with Urgency and Focus: Prioritize what matters and find the shortcuts.
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Own the Outcome: Take initiative and see it through until the end.
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Commit to Your Craft: Excellence is the standard, care about the details.
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Play to Win: If we win, Americans win, so we work hard and do what it takes for us to be #1.
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Feedback is Fuel: Intellectual honesty is at the core of everything we do.
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We’re One Team: Together, we can achieve things that none of us could on our own.
📩 Interested?
Send us a note. Tell us why this mission matters to you and how you'd make an impact.
Top Skills
What We Do
Medical bills are a massive problem. They are confusing, over 40% contain errors, 17% of claims are denied by insurance, and often represent very large sums of money. As a result, 100 million Americans are saddled with medical debt, and medical bills cause nearly 70% of personal bankruptcies in the US.
Dealing with unexpectedly high medical bills is time-consuming, complex, and stressful. Stuck between their providers, payers, and bill collectors, consumers too frequently have to make numerous phone calls, wait on hold, and even send paper letters and faxes. Appealing insurance denials, resolving billing errors, negotiating bills, and filing out of network claims require expert knowledge that most consumers don't have.
Thanks to AI and new healthcare regulations around data access and price transparency, we can now automate this soul-crushing work and empower consumers to fight back against this broken system. Beyond medical bills, we help people through their entire healthcare journey as they pick their health insurance plans and benefits, or look for care that fits their budget.
We’re lucky to be backed by the founders and investors at Hugging Face, Oscar Health, TrueBill, CaseText, Forerunner Ventures, Red Sea Ventures, RRE Ventures, and much more. We are well-funded for the next few years.
Why Work With Us
MedBill AI is founded by 2 Oscar Health veterans, the first health insurance company built around a full stack technology platform and a relentless focus on serving its members. We joined Oscar pre-product, stayed through the IPO and helped it grow to over 1M members. We’re excited to have an even larger impact with MedBill AI.
