Head of Litigation

Stedi is hiring a Head of Litigation to aggressively protect and expand their freedom to operate in the healthcare sector. Stedi is building the first new healthcare clearinghouse in decades, disrupting an industry dominated by legacy players.

The role involves handling antitrust, information blocking, HIPAA Administrative Simplification, complex commercial disputes, and regulatory challenges related to payments and Treasury. The Health Insurance Portability and Accountability Act (HIPAA) mandates standardized X12 HIPAA transactions for insurance exchanges, and clearinghouses like Stedi process the majority of these transactions.

Stedi is facing entrenched incumbents with vested interests in preserving the current structure. The Head of Litigation will own both affirmative and defensive legal strategies, including demand letters, regulatory filings, and litigation. The role is proactive, focusing on shaping disputes before they escalate.

What You’ll Do:

• Own affirmative disputes, from theory development and demand letters to regulatory complaints and litigation.
• Build a record proactively, forming strategies for investigations, preservation, and data analysis to ensure credibility.
• Manage the regulatory-enforcement track, including HIPAA complaints, state insurance regulators, and antitrust authorities.
• Defend the company across commercial, customer, and other disputes.
• Oversee outside counsel selection, scope, and budget, retaining specialists while keeping work in-house where feasible.
• Translate disputes into commercial outcomes, collaborating with the CEO and Legal/Policy teams to determine settlements, contract changes, direct payer connections, or judgments.
• Build and automate legal infrastructure, including litigation holds, preservation, discovery readiness, and matter tracking.
• Keep leadership informed with honest assessments and sophisticated reasoning.

Who You Are:

• At least 12+ years of experience litigating complex commercial disputes, with first-chair experience.
• Strategic thinker, adept at determining when and how to use laws and regulations affirmatively.
• Experience initiating cases, not just defending them.
• Depth in antitrust, unfair competition, complex contract disputes, and regulatory enforcement. Healthcare and technology backgrounds are strongly preferred; experience in other regulated industries (financial services, payments, insurance, telecom) will also be considered.
• Resourceful and cost-conscious, prioritizing in-house solutions where possible.
• Strong judgment and realistic assessment of odds, capable of identifying weaknesses in positions before opposing counsel does.
• Exceptional writer, with work product requiring minimal edits.
• Credible with engineers, able to follow technical conversations about APIs and understand their significance.
• Fast-paced and capable of keeping up with Stedi’s rapid pace.
• Alignment with Stedi’s philosophical standards.
• JD and membership in at least one U.S. state bar.