Alan Rosa is a Fortune-scale technology executive with more than 25 years of experience leading enterprise transformation across AI, cybersecurity, infrastructure, and operational resilience. As SVP and CISO of Infrastructure & Technical Operations at CVS Health, he oversees 4,000+ technologists and more than $1.7B in annual technology investment, operating and securing the digital backbone of one of the world’s largest healthcare enterprises. Alan has led large-scale modernization initiatives that translate complex technology change into measurable business outcomes—driving growth, reducing risk, and strengthening customer trust—through multi-cloud transformation, AI and automation adoption, and zero-trust security frameworks. Prior to CVS, he held senior leadership roles at Twitter, Madison Square Garden, Marriott, Disney, and NBCUniversal. With a leadership philosophy grounded in trust, accountability, and governance, and informed by formal legal training, Alan partners closely with executive teams and boards to align innovation with risk management and long-term enterprise value.