Head of Litigation

Openkrill; United States; Remote; USD 250,000 - 350,000; Full time

Job summary

Stedi is building a new healthcare clearinghouse and seeks a Head of Litigation to own all major disputes, from theory and data analysis to demand letters, regulatory filings, and litigation. You will partner with executive leadership and outside counsel to advance strategic outcomes and protect the company’s interests.

The role demands 12+ years of complex disputes experience with first-chair exposure, strong writing, and the ability to drive settlements or courtroom actions.

Qualifications

• 12+ years litigating complex commercial disputes with first-chair experience.
• Experience driving strategy and outcomes in regulatory and antitrust matters.
• Background in healthcare and technology is strongly preferred.

Responsibilities

• Own affirmative disputes from theory to litigation and settlements.
• Build the record, direct investigations, and data analysis for credibility.
• Run regulatory-enforcement and antitrust tracks alongside litigation.
• Defend the company across disputes and manage external counsel.
• Oversee outside counsel selection, scope, and budget with in-house alignment.
• Translate disputes into commercial outcomes with leadership input.
• Create litigation infrastructure and automate processes for efficiency.
• Provide honest assessments to leadership and maintain pace with the business.

Skills

First-chair experience

Legal strategy

Regulatory enforcement

Antitrust/UCF experience

Healthcare/tech background

Strong writing

Budget-conscious

Credible with engineers

Education

J.D. and bar admission (US)

Job description

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. Our clearinghouse product and customer-first approach have set us apart. Stedi was ranked by Ramp https://ramp.com/data/top-saas-vendors-on-ramp-march-2026 as one of the fastest-growing SaaS vendors.

Stedi has lightning in a bottle: engineers and designers shipping products week in and week out; a lean business team supporting the company's infrastructure; a passion for automation and eliminating toil; and $142 million in funding from top investors like Stripe, Addition, USV, Bloomberg Beta, First Round Capital, and more.

To see what we ship, watch the 2026 Stedi Keynote https://www.youtube.com/watch?v=MxyCUNAr9Y8. To learn more about how we work, watch our founder Zack's interview with First Round Capital https://www.youtube.com/watch?v=IO6sR-i5rSs.

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.

In the healthcare sector, the Health Insurance Portability and Accountability Act of 1996 (HIPAA) requires that all insurance payers exchange transactions such as claims, eligibility checks, prior authorizations, and remittances using a standardized EDI format called X12 HIPAA. Clearinghouses process the majority of these transactions, offering consolidated connectivity to carriers and providers.

Who can reach which payers, and on what terms, is often determined by routing arrangements, exclusive relationships, and contractual terms rather than by product quality or customer choice. As Stedi continues to grow, we're facing legacy incumbents with a vested interest in preserving this structure.

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.

We're looking for an exceptional lawyer to own the work, partnering closely with executive leadership and outside counsel where the specialization calls for it. Winning here may be a settlement or judgment, but it also could be a previously exclusive payer connecting to us directly, a term coming out of a contract, a regulator issuing guidance, or a practice quietly ending. The job takes the judgment to know which outcome best advances Stedi's interests and the skill and resolve to take matters as far as they need to go.

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.

We've been made aware of individuals impersonating the Stedi recruiting team. Please note:

• All official communication about roles at Stedi will only come from an @stedi.com http://stedi.com email address, or from our official identification verification partner, Persona, @frompersona.com http://frompersona.com.
• If you're unsure whether a message is legitimate or have any concerns, feel free to contact us directly at [e-mail].

We appreciate your attention to this and your interest in joining Stedi.

At Stedi, we're looking for people who are deeply curious and aligned to our ways of working.