We're building a new healthcare clearinghouse

Stedi is the only headless clearinghouse and RCM engine. Headless means every part of our product is accessible via API. Developers and AI agents build their own interface on top of it. By offering modern, AI-ready APIs alongside traditional real-time and batch EDI processes, we enable both healthcare technology businesses and established players to exchange mission-critical transactions.

What we’re looking for

Stedi is hiring a Head of Litigation to aggressively protect and expand our freedom to operate. Stedi is building the first new healthcare clearinghouse in decades and rapidly winning in an industry that has been occupied entirely by a concentrated, entrenched group of legacy players.

The work spans antitrust, information blocking, HIPAA Administrative Simplification, complex commercial disputes, and the regulatory questions created by our expansion into payments and Treasury.

A steady supply of legal fights always follows disruptive technology. We're hiring a Head of Litigation to own this work. The role is affirmative before it is defensive. You'll form and drive the matters we bring, from theory and evidentiary development through demand letters, regulatory filings, and litigation. You'll also handle what comes at us as we scale into new products and new lines of business.

What you’ll do

• Own Stedi's affirmative disputes from theory, factual development, and demand letters to regulatory complaints and litigation.
• Build the record before there's a case. Form strategies and direct investigations, preservation, and data analysis accordingly, so a claim is credible the day it's raised.
• Run the regulatory-enforcement track alongside the litigation track. HIPAA Administrative Simplification complaints, state insurance regulators, and federal and state antitrust authorities are potential instruments here, and you'll know which one fits the problem in front of you.
• Defend the company across commercial, customer, and any other disputes.
• Own outside counsel selection, scope, and budget. Retain specialists deliberately, keep the work in-house wherever it can be done in-house, and hold firms to the standards we hold ourselves to.
• Translate disputes into commercial outcomes, working with the CEO and our Legal and Policy teams on where a matter should land: a settlement, contract change, direct payer connection, or judgment.
• Build legal infrastructure – litigation holds, preservation and discovery readiness, privilege hygiene, matter tracking – and automate enough of it that a lean team can run it.
• Keep leadership calibrated with honest assessments and sophisticated reasoning.

Who you are

• 12+ years litigating complex commercial disputes, with first-chair experience.
• Strategic. Much of this role is determining when and how to wield the laws and regulations affirmatively.
• You've been on the initiating side and built cases – not only answered them.
• Depth in some combination of antitrust and unfair competition, complex contract disputes, and regulatory enforcement. Healthcare and technology backgrounds are strongly preferred; we'll also consider deep experience in another heavily regulated, complex industry (financial services, payments, insurance, telecom).
• Resourceful and frugal. Your first instinct is not to hand the matter to a big firm and approve the budget.
• Strong judgment and realistic about odds. You’re able to gauge a matter and tell us what's weak in our position before opposing counsel does – and you're equally clear about when not to pursue it.
• A strong writer. The output of this role will be centered around written work, and your work product should need very little from anyone else.
• Credible with engineers. You can follow a conversation about APIs and understand why the details matter.
• Fast. We move quickly and expect legal to keep pace.
• Philosophical alignment with the Stedi Standards.
• JD and membership in at least one U.S. state bar.