Founding Head of Operations
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AI Summary
Design and own the end-to-end claims workflow, integrating AI agents and human operators to optimize healthcare payment disputes. Translate real-world operational patterns into technical specifications to drive product development alongside engineering.
Founding Head of Operations
Design the operating system of a healthcare AI company. Write the specs. Ship the product.
Location: San Francisco or Remote | Full Time
Why This Exists
A federal arbitration system called Independent Dispute Resolution, or IDR, now determines billions of dollars in healthcare payments each year. Providers win the vast majority of disputes, yet most eligible claims are never filed. The process is manual, fragmented, and resource-intensive, and most providers don't have the infrastructure to pursue what they're owed.
The No Surprises Act created the framework, and the market already exists. Today it runs on spreadsheets, consultants, and static playbooks. We're building the first intelligent system designed to operate inside it.
Operations is where that system meets reality. Every claim goes through a workflow that spans ingestion, eligibility, evidence packaging, submission, and settlement. Every new payer behavior, every regulatory shift, every customer exception shows up here first. The person running this function shapes how the company actually works, and what the product actually becomes.
Why This Is Hard (and Interesting)
Most operations leaders inherit a process and optimize it. You will not inherit a process. You will design the process, write the specs, and build the tools alongside engineering.
Healthcare revenue cycle teaches you the domain: inconsistent claims data, payers that adapt, deadlines that cascade, audit trails that matter. That's the foundation. What's new is that many of the people running these workflows will increasingly be AI agents, not offshore teams. That changes the shape of the job.
You will write specs and ship them. Sometimes with engineers, sometimes by driving agents yourself. You will design how claims move through the system when half the steps are automated. You will build dashboards and SOPs that treat AI as a first-class team member. If you have been watching AI-native operating patterns emerge and want to put them into practice in a high-stakes domain, this is a rare seat.
Who We Are
Recourse is being built in partnership with 25M Health, a healthtech venture firm. We have institutional backing, a shared platform team spanning engineering, strategy, design, and back-office, and early access to large provider systems.
We are actively working with health system design partners and have access to $400M+ in billable claims to inform product development from day one. This is a funded, validated opportunity with real customers and real data.
We are small. We move quickly. We value clarity over theater. We want this to be the best work of your career. The stretch you look back on as the one where you shipped real things, with people who raised your game, on something that mattered.
We care about clear thinking, high ownership, intellectual honesty, and direct communication. We believe operations, product, and engineering should operate as one pod, not three functions. We believe in giving people real ownership and trusting them to rise to it. We want the machines to do machine work, and the humans to do their best work. The person in this role is central to making that real.
The Role
As Founding Head of Operations, you will own how Recourse runs its claims workflow, and how that workflow gets encoded into product. You will:
- Own end-to-end claim operations: ingestion, eligibility, evidence packaging, submission, settlement tracking
- Turn real-world claim patterns into specs and drive them to production, often by steering agents yourself
- Design the division of labor between AI agents, human operators, and customer teams
- Build the operating cadence: OKRs, weekly rhythms, throughput metrics, quality standards
- Stand up partner onboarding and customer success for provider and legal-partner relationships
- Partner closely with the Head of Engineering to ship product, not just document requirements
- Use AI tooling directly (Claude Code, Codex, Cursor, agentic frameworks) to move specs, data, and early features forward without waiting on engineering cycles
- Build the playbook as we scale from dozens of claims to thousands
This is not a classic COO role and it is not a classic head-of-ops role. It is the person who makes sure the product matches the work, and the work matches the product. You will write code-adjacent artifacts (specs, workflow diagrams, AI prompts) and you will ship.
Who You Are
You are AI-pilled. You have opinions about which agentic frameworks matter, which ones are hype, and which tools you reach for first. You have already used AI to do work that would have taken a team. You stay current not because it is trendy, but because the world is changing and you want to see the next shift before anyone else.
You have strong operational common sense. You can walk into a messy process, figure out what actually matters, and produce a clean system. You are not precious about methodology. The goal is throughput and quality, not frameworks.
You have a bias to action. You don't default to no. Speed of iteration over polish of iteration. You start, you learn, you fix things in motion. Most decisions are reversible and do not need extensive study.
You have technical fluency. You're comfortable working with data, querying systems directly, and getting hands on to move work forward rather than waiting for engineering cycles. You do not need to be a senior engineer. You do need to collaborate with engineers as a peer. If there's a spec to write, you write it. If there's a Claude prompt to iterate on, you iterate.
You understand healthcare, ideally revenue cycle. You know what an 835 is. You have seen how claims actually move through a hospital billing department. You have strong intuitions for where payers push back and where providers leave money on the table.
You are intellectually honest and curious. You seek out the things that might disconfirm your beliefs, not just confirm them. When you don't understand something, you keep digging. When you're wrong, you say so. You use plain language. You respectfully challenge decisions you disagree with, and once a decision is made, you commit. In a domain as messy as healthcare claims, that honesty is worth more than false confidence.
You put the team first. You are reliable and fully invested. You know sustainable intensity beats burnout. You take your vacations. You check on your teammates. You build a culture where people do their best work because they are supported, not squeezed.
What You Bring
- 5+ years of operations leadership, ideally spanning healthcare revenue cycle, claims operations, or a similarly regulated domain
- A track record of designing and running workflows at scale, not just documenting them
- Meaningful technical fluency: comfort with data, analytical tools, and getting hands on to move work without waiting on engineering
- Deep familiarity with AI tooling (Claude, ChatGPT, Cursor, agentic frameworks). You have shipped things using them, not just demo'd them
- Experience writing product specs, user stories, or equivalent artifacts that can be built against
- A preference for small teams and early-stage chaos over mature org charts
- Experience managing outside partners (law firms, vendors, offshore teams, customer ops) is a strong plus
- Familiarity with the No Surprises Act, IDR, payer contracting, or out-of-network claims is a major plus
Experience designing systems where correctness, auditability, and financial impact are tightly coupled is highly valued.
Sound judgment, operational depth, and ownership mindset are required.
Why This Role
This is a chance to define the operating layer of a new company in healthcare payments. You will run a real workflow, ship real product, and work with AI as a true collaborator, not a toy. You will do it with institutional backing and early-stage ownership. No startup koolaid, no theater, just real work with real outcomes.
If you want this to be the most memorable stretch of your career, where you shipped something real, with a team you respected, in a domain that actually matters, this is the seat. We would like to talk.
Compensation
Base salary range: $150,000 to $200,000, with meaningful equity. Specific offers are calibrated to experience, location, and scope of the role. We also cover standard health, dental, and vision benefits, and expect our team to take real vacation time.
Equal Opportunity
Recourse is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law. We believe the best teams are built from people with different backgrounds and perspectives, and we're committed to creating an environment where everyone can do their best work.
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