Head of Litigation

Accountabilities: Own affirmative litigation and disputes, from developing legal theories and building factual records to issuing demand letters, filing regulatory complaints, and pursuing litigation. Lead investigations and evidence development before disputes formally arise, including directing data analysis, document preservation, and fact-finding to build credible, well-supported cases. Develop and execute strategies involving antitrust, unfair competition, complex commercial contracts, and regulatory enforcement. Determine when to pursue litigation, regulatory action, negotiated settlements, contractual changes, or other outcomes that advance the organization's commercial interests. Manage regulatory enforcement initiatives involving HIPAA Administrative Simplification, state insurance regulators, and federal and state antitrust authorities. Defend the organization in commercial, customer-related, and other disputes as its products, services, and business operations expand. Partner closely with executive leadership and internal Legal and Policy teams to align litigation strategy with business priorities and long-term growth. Select, manage, and oversee outside counsel, including defining engagement scope, controlling budgets, and ensuring high-quality, cost-effective legal work. Build and maintain litigation infrastructure, including litigation holds, document preservation, discovery readiness, privilege management, and matter tracking. Identify opportunities to automate legal workflows and processes so a lean team can manage complex matters efficiently. Provide leadership with candid, well-reasoned assessments of legal risks, potential outcomes, strategic trade-offs, and the strengths and weaknesses of individual matters. Monitor legal and regulatory developments affecting healthcare transaction infrastructure, technology, payments, and related regulated industries. Requirements: 12+ years of experience litigating complex commercial disputes, including substantial first-chair litigation experience. Demonstrated experience initiating disputes and building affirmative cases, rather than focusing exclusively on defense. Deep expertise in a combination of antitrust, unfair competition, complex contractual disputes, and regulatory enforcement. Healthcare and technology industry experience strongly preferred; candidates with substantial experience in other complex, highly regulated industries such as financial services, payments, insurance, or telecommunications will also be considered. Strong strategic judgment and the ability to determine when affirmative legal action is warranted, how to pursue it, and when an alternative approach would be more effective. Proven ability to develop litigation strategy, direct investigations, evaluate evidence, and build persuasive legal arguments from the ground up. Excellent legal writing skills, with the ability to produce polished, rigorous, and self-sufficient written work with minimal additional support. Commercial awareness and practical decision-making skills, including the ability to connect legal outcomes with business objectives. Experience selecting and managing outside counsel, controlling legal budgets, and maintaining a resourceful, cost-conscious approach to litigation. Strong understanding of legal risk assessment, with the ability to communicate uncertainty, identify weaknesses in a case, and provide clear recommendations to senior leadership. Ability to engage credibly with technical teams, understand discussions involving APIs and software infrastructure, and appreciate the legal significance of technical details. Ability to work quickly and independently in a fast-paced, technology-focused environment while maintaining sound judgment and high standards. Strong communication and collaboration skills, particularly when working with executive leadership, Legal, Policy, engineering, and external counsel. Alignment with a culture that values curiosity, ownership, high standards, thoughtful decision-making, and efficient execution. Juris Doctor (JD) degree and active membership in at least one U.S. state bar. Benefits: Opportunity to lead high-impact litigation and regulatory strategy in a rapidly evolving healthcare technology sector. Significant autonomy and direct partnership with executive leadership on critical legal and commercial decisions. The ability to shape affirmative legal strategy and influence industry practices, competitive access, and contractual relationships. A remote work arrangement within the United States. A lean, technology-oriented working environment that values automation, efficiency, and individual ownership. Opportunities to collaborate with experienced technical, legal, policy, and business teams on complex, consequential challenges. Salary, equity, healthcare coverage, retirement benefits, paid time off, and other specific compensation details were not provided in the original listing.