Head of Litigation

This is a unique opportunity for an experienced litigation leader to shape legal strategy at a fast-growing healthcare technology company transforming how healthcare transactions are exchanged. As Head of Litigation, you will lead both affirmative legal actions and defensive disputes, helping protect and expand the organization's freedom to operate in a complex, highly regulated industry. Your work will span antitrust, unfair competition, commercial disputes, healthcare regulations, and emerging legal questions related to payments and financial services. You will partner directly with executive leadership, internal Legal and Policy teams, and carefully selected outside counsel to turn legal strategy into meaningful commercial outcomes. In a lean, technology-driven environment, you will build cases proactively, modernize litigation processes, and use automation to improve efficiency. This role offers substantial ownership, strategic influence, and the opportunity to help shape competitive dynamics across the healthcare technology ecosystem.

• 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.