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Stedi is a Series B-funded healthcare clearinghouse and RCM (Revenue Cycle Management) platform built on modern, API-first architecture. The company has raised $142M from top-tier investors including Stripe, Addition, USV, and Bloomberg Beta, and is ranked among the fastest-growing SaaS vendors. Stedi is disrupting a decades-old industry dominated by entrenched legacy players by offering the first new healthcare clearinghouse in decades with headless, developer-friendly APIs.
As Head of Litigation, you will own Stedi's affirmative and defensive legal strategy across multiple complex domains. This is a high-impact role reporting to executive leadership, responsible for protecting and expanding the company's freedom to operate in a heavily regulated, competitive landscape.
Key responsibilities include:
- Own affirmative disputes from initial theory and factual development through demand letters, regulatory complaints, and litigation. You will be the first-chair attorney on complex matters.
- Build the evidentiary record proactively before disputes arise. Form litigation strategies, direct investigations and data analysis, and develop credible claims from day one.
- Run parallel regulatory-enforcement tracks alongside litigation. Navigate HIPAA Administrative Simplification complaints, state insurance regulators, and federal/state antitrust authorities as strategic instruments.
- Defend the company across commercial, customer, and other disputes.
- Own outside counsel selection, retention, scope, and budget. Retain specialists strategically, keep work in-house where feasible, and maintain high standards.
- Translate disputes into commercial outcomes by partnering with the CEO and Legal/Policy teams to determine optimal resolutions: settlements, contract modifications, direct payer relationships, or judgments.
- Build and automate legal infrastructure including litigation holds, preservation and discovery readiness, privilege hygiene, and matter tracking to enable a lean team to operate at scale.
- Provide executive leadership with honest, sophisticated assessments and calibrated risk analysis.
The role spans antitrust, information blocking, HIPAA Administrative Simplification, complex commercial disputes, and regulatory questions arising from Stedi's expansion into payments and treasury services. Much of the work is affirmative—determining when and how to wield laws and regulations strategically to advance company interests.
Requirements:
- 12+ years of experience litigating complex commercial disputes with first-chair trial or motion experience.
- Strategic mindset with demonstrated ability to initiate and build cases, not only defend them.
- Deep expertise in some combination of: antitrust and unfair competition law, complex contract disputes, and regulatory enforcement. Healthcare and technology backgrounds strongly preferred; deep experience in other heavily regulated industries (financial services, payments, insurance, telecom) also considered.
- Resourceful and cost-conscious approach to legal spend; preference for in-house work over outsourcing.
- Strong judgment and realistic assessment of case odds. Ability to identify weaknesses in your own position early.
- Excellent written communication skills; work product should require minimal editing.
- Ability to understand technical concepts (APIs, software architecture) and engage credibly with engineers.
- Fast-moving mindset aligned with startup pace and Stedi's operational standards.
- Juris Doctor (JD) and active membership in at least one U.S. state bar.
