Adam McAnaney serves as Chief Legal Officer at Oscar Health, Inc. (NYSE: OSCR), a leading health insurance company revolutionizing the healthcare experience through technology-driven solutions. With over two decades of experience in corporate law, particularly in fintech, healthtech, and regulated industries, McAnaney brings a proven track record of navigating complex regulatory landscapes and scaling legal operations for high-growth companies. He holds a J.D. from Harvard Law School and a B.A. from the University of Notre Dame, where he graduated summa cum laude. Prior to joining Oscar in 2022, McAnaney was General Counsel for Square Capital (now Block, Inc.), where he led legal strategy for the company's $10 billion+ lending platform, overseeing compliance, product launches, and high-stakes litigation that resulted in zero major regulatory penalties during his tenure. His earlier career included stints at premier law firms such as Cooley LLP and Simpson Thacher & Bartlett, advising on mergers, IPOs, and venture financings for tech unicorns. Notable achievements include guiding Square through its public debut and structuring innovative financial products that expanded access to capital for small businesses amid evolving U.S. regulations. At Oscar Health, McAnaney directs a world-class legal team focused on regulatory affairs, corporate governance, intellectual property, and risk management, playing a pivotal role in the company's expansion into new markets and Medicare Advantage. Under his leadership, Oscar has achieved key milestones, including successful state expansions and strengthened compliance frameworks that supported a 50%+ year-over-year membership growth in 2023. His strategic foresight continues to position Oscar as a compliant innovator in the $1 trillion health insurance sector.