[Hiring] Head of Litigation @Stedi

Role Description

Stedi is hiring a Head of Litigation to aggressively protect and expand our freedom to operate. The work spans:

• Antitrust
• Information blocking
• HIPAA Administrative Simplification
• Complex commercial disputes
• Regulatory questions created by our expansion into payments and Treasury

As Stedi continues to grow, we're facing legacy incumbents with a vested interest in preserving existing structures. A steady supply of legal fights follows disruptive technology, and 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.

Winning here may be a settlement or judgment, but it could also involve:

• A previously exclusive payer connecting to us directly
• A term coming out of a contract
• A regulator issuing guidance
• A practice quietly ending

The job requires 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.

Qualifications

• 12+ years litigating complex commercial disputes, with first-chair experience
• Strategic mindset for determining when and how to wield laws and regulations affirmatively
• Experience on the initiating side, building cases
• Depth in antitrust and unfair competition, complex contract disputes, and regulatory enforcement
• Healthcare and technology backgrounds preferred; experience in other heavily regulated industries considered
• Resourceful and frugal approach to legal matters
• Strong judgment and realistic assessment of odds
• Strong writing skills with minimal need for editing
• Credible with engineers and understanding of APIs
• Ability to move quickly in a fast-paced environment
• Philosophical alignment with the Stedi Standards
• JD and membership in at least one U.S. state bar

Requirements

• 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, forming strategies and directing investigations
• Run the regulatory-enforcement track alongside the litigation track
• Defend the company across commercial, customer, and other disputes
• Own outside counsel selection, scope, and budget
• Translate disputes into commercial outcomes with executive leadership
• Build legal infrastructure and automate processes for efficiency
• Keep leadership calibrated with honest assessments and sophisticated reasoning

Benefits

• Competitive salary
• Comprehensive health benefits
• Flexible work environment
• Opportunities for professional development

Company Description

Stedi is the only headless clearinghouse and RCM engine, offering modern, AI-ready APIs alongside traditional real-time and batch EDI processes. Our approach has set us apart in the healthcare technology industry.

• Ranked by Ramp as one of the fastest-growing SaaS vendors
• $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 . To learn more about how we work, watch our founder Zack's interview with First Round Capital .