Director/Senior Legal Counsel – Medicare, Healthcare Regulatory & Contracting

About Judi Health Judi Health is an enterprise health technology company providing a comprehensive suite of solutions for employers and health plans, including: Judi Rx , a public benefit corporation delivering full-service pharmacy benefit management (PBM) solutions to self-insured employers, Judi Health™ , which offers full-service health benefit management solutions to employers, TPAs, and health plans, and Judi® , the industry’s leading proprietary Enterprise Health Platform (EHP), which consolidates all claim administration-related workflows in one scalable, secure platform. Together with our clients, we’re rebuilding trust in healthcare in the U.S. and deploying the infrastructure we need for the care we deserve. To learn more, visit www.judi.health . Location: Hybrid (at least 3 days per week in our NYC, Denver, or Charlotte offices) Position Summary We are seeking an experienced and business-oriented healthcare attorney to join our Legal team. This role will serve as a strategic legal advisor to senior leadership and business partners, providing legal support across Medicare Part D, healthcare regulatory compliance, contracting, and operational initiatives. The successful candidate will have deep experience with Medicare, health insurance and healthcare laws, substantial healthcare contracting expertise, and the ability to provide practical legal advice that balances regulatory requirements with business objectives. This attorney will play a key role in supporting a rapidly growing healthcare organization operating in a highly regulated environment. Position Responsibilities: Medicare & Healthcare Regulatory Compliance/Contracting Provide legal advice regarding Medicare Part D, health insurance and other federal healthcare program requirements. Counsel business teams on CMS regulations, guidance, audits, reporting obligations, and regulatory enforcement matters. Monitor and interpret changes in healthcare laws and regulations and advise leadership regarding operational impacts. Support regulatory change management initiatives and implementation of new legal requirements. Advise on regulatory risks associated with business operations, products, and strategic initiatives. Assist with government audits, investigations, corrective action plans, and responses to regulatory inquiries. Draft, review, negotiate, and advise on a broad range of healthcare and commercial agreements, including: Rebate and delegation agreements Client agreements Network and managed care contracts Develop contracting standards, templates, negotiation playbooks, and risk management processes. Partner with procurement, operations, compliance, and business teams to facilitate efficient contract review and execution. Support vendor selection, due diligence, onboarding, and ongoing oversight activities. Provide legal guidance on: False Claims Act Anti-Kickback Statute Stark Law Medicare and Medicaid requirements State insurance and healthcare regulations Support compliance investigations, policy development, training initiatives, and operational audits. Provide practical, solution-oriented legal guidance aligned with business objectives. Identify legal risks and develop creative, operationally feasible solutions. Support corporate growth initiatives, product development, and strategic transactions as needed. Required Qualifications Juris Doctor (J.D.) from an accredited law school. Active license and good standing in at least one U.S. state. 8+ years of legal experience in a law firm, healthcare organization, health plan, PBM, managed care organization, or combination thereof. Significant experience with Medicare Part D regulatory requirements. Extensive healthcare contracting experience, including complex commercial and vendor agreements. Strong knowledge of federal and state healthcare laws and regulations. Experience advising cross-functional business teams in a fast-paced environment. Excellent drafting, negotiation, analytical, and communication skills. Demonstrated ability to manage multiple priorities independently. Preferred Qualifications: Experience supporting Medicare Advantage plans, PBMs, health plans, TPAs, or managed care organizations. Experience with CMS audits, corrective action plans, and regulatory examinations. Knowledge of delegated entity and FDR oversight requirements. Experience with provider contracting and network management. Experience with healthcare technology, data privacy, and digital health products. Familiarity with Medicaid and commercial health plan regulations. Experience supporting mergers, acquisitions, and strategic healthcare transactions. Critical Competencies: Medicare and CMS regulatory expertise Healthcare and vendor contracting Healthcare compliance and risk management Business-oriented legal judgment Practical problem-solving Project management and organizational skills Collaboration across legal, compliance, operations, and business teams Why This Role Matters This attorney will serve as a key member of the Legal organization, helping the company scale responsibly while navigating complex Medicare, healthcare regulatory, and contracting obligations. The role offers the opportunity to shape legal strategy, influence business decisions, and build processes that support continued growth and operational excellence. This range represents the low and high end of the anticipated base salary range. The actual base salary will depend on several factors such as: experience, knowledge, skills, and location of the job. Remote, US Salary Range $130,800 — $206,500 USD New York, NY Salary Range $165,200 — $206,500 USD Denver, CO Salary Range $151,200 — $189,000 USD Charlotte, NC Salary Range $137,600 — $172,000 USD All employees are responsible for adherence to the Judi Health Code of Conduct including the reporting of non-compliance. This position description is designed to be flexible, allowing management the opportunity to assign or reassign duties and responsibilities as needed to best meet organizational goals. We provide equal employment opportunities to all employees and applicants for employment and prohibit discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, medical condition, genetic information, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. By submitting an application, you agree to the retention of your personal data for consideration for a future position at Judi Health. More details about Judi Health's privacy practices can be found at https://www.judi.health/legal/privacy-policy .