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Head of Litigation

Stedi· Business
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RemoteFull-timePosted 2w ago

About the role

Lead and manage affirmative litigation and regulatory enforcement initiatives to protect and expand Stedi’s freedom to operate in the healthcare clearinghouse space. Own matters from theory and evidentiary development through demand letters, regulatory filings, and litigation; build legal infrastructure and collaborate with executive leadership to achieve commercial outcomes.

Responsibilities

  • 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.

Qualifications

  • 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.

Skills

Required:Litigation strategyRegulatory enforcementLegal writing
Last updated Oct 8, 2026. Interested? Apply on the company site.

About Stedi

The only programmable healthcare clearinghouse

Stedi is the only programmable healthcare clearinghouse. We offer modern, AI-ready APIs for eligibility checks, claims, transaction enrollment, and more.

healthcareAPIssoftwarehealth tech
Company profileWebsite

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