Associate General Counsel, Healthcare and Technology

About us Pomelo Care is the leading virtual medical practice for women and children, providing care across pregnancy, postpartum, pediatrics, menopause, and perimenopause. We combine proactive, 24/7 clinical care with technology that helps us reach patients earlier, identify risks sooner, and deliver personalized care throughout their journey. Our team includes clinicians, technologists, operators, and problem-solvers working together to make high-quality care more accessible for families nationwide. About The Role: We are looking for a seasoned healthcare attorney and strategic legal leader to join our Legal, Privacy and Compliance team as our Associate General Counsel, Healthcare and Technology. You’ll focus on legal matters at the intersection of healthcare, product, privacy, and AI governance. You will serve as a strategic partner to the GC, helping shape legal strategy and providing decision support on high-priority business initiatives. You will partner with cross-functional teams to provide practical, risk-informed guidance as Pomelo develops new products, care delivery models, and technology-enabled workflows. This role is built for a senior attorney who combines deep healthcare regulatory judgment with practical product and privacy counseling, and who can flex into adjacent legal needs as Pomelo scales. If you’re passionate about the intersection of technology and healthcare, this is an opportunity to have a significant and visible impact on our business. This role reports to the General Counsel and is open to any candidates located in the continental US. What You'll Do: Senior Legal Partner: Serve as a senior legal partner on matters connected to your primary focus areas, providing sound, business-aligned guidance that enables the business to move quickly while managing risk appropriately. Partner closely with the GC on high-priority matters and flex into other legal needs as the business evolves. Product, Regulatory & Privacy Counseling: Provide legal guidance on matters at the intersection of product development, healthcare regulation, privacy, and care delivery. Serve as a trusted legal resource for product, engineering, clinical, and operations teams, providing practical, risk-informed guidance as new features, clinical tools, care delivery models, and consumer-facing products move toward launch. Bring deep regulatory expertise to bear on new market entry, evolving business models, and cross-functional initiatives, in partnership with compliance and legal colleagues. AI Governance: Lead and mature our responsible AI governance program, partnering with cross-functional leaders to ensure that our AI initiatives balance strategic business goals with regulatory compliance. Who You Are: JD from an accredited law school with active U.S. bar membership. 10+ years of legal experience – with a blend of law firm and in-house roles in health tech or digital health. In-house experience at a fast-paced healthcare or health tech company is required. Expert-level knowledge of healthcare regulatory law, including fraud and abuse laws (AKS, FCA, Stark Law), CPOM, telehealth regulations, and Medicaid reimbursement. Deep experience advising on high-stakes product development and app deployment, with a proven ability to manage rapid iteration in a technology-driven environment. Sophisticated understanding of U.S. privacy laws (HIPAA and state consumer laws) and regulations impacting consumer-facing healthcare models. Demonstrated experience leading AI/ML governance initiatives, including an understanding of the legal and ethical implications of AI in clinical settings. Excellent communication and analytical skills with the ability to translate complex legal concepts into actionable business guidance. Strong professional judgment with a proven ability to manage up effectively, providing the GC with proactive communication and decision support while maintaining clear ownership of assigned matters. A mentor-leader with direct managemen