Safra Catz vs Stacey Caywood

Safra Catz

CEO of Oracle

BIO: Safra A. Catz is the Chief Executive Officer of Oracle Corporation and a member of the company’s Board of Directors. At Oracle, she previously served as President, Chief Financial Officer, Executive Vice President, and Senior Vice President. She is also a lecturer on the faculty of the Stanford Graduate School of Business. She has been a member of the Board of Directors of the Oracle Education Foundation since its founding in 2000 and has served as Chair since 2004. Safra is on the Board of Trustees of In-Q-Tel. Previous to Oracle, she held various positions at Donaldson, Lufkin & Jenrette including Managing Director in Investment Banking. Safra also served on the Board of Directors for HSBC Holdings and The Walt Disney Company.

Stacey Caywood

CEO of Wolters Kluwer

BIO: Stacey is Chief Executive Officer and Chair of the Executive Board of Wolters Kluwer since February 2026, and a Member of the Executive Board since 2025. From 2020 to 2025, Stacey served as CEO of Wolters Kluwer Health where she led the further evolution and development of Wolters Kluwer's healthcare solutions, ensuring medical and nursing professionals around the world can benefit from advanced clinical technology and evidence-based data and insights. Previously, as CEO of Wolters Kluwer Legal & Regulatory, she led a strategic transformation across Europe and the U.S., returning the business to organic growth. Earlier in her career, Stacey was President and CEO of Wolters Kluwer Law & Business, and held several management and leadership roles of increasing responsibility within the Company. Stacey is a seasoned executive with extensive experience. She excels in business transformation, digital revenue growth, and innovation across legal, compliance, and healthcare markets. Her expertise spans strategy execution, portfolio management and M&A, product innovation, and commercial excellence. In 2021, Stacey received a Female Executive of the Year Stevie® Award in the Business Products category in recognition of her leadership while navigating the healthcare markets and piloting a workforce to support the frontlines during the COVID-19 pandemic. Stacey earned an MBA from Northwestern University, J.L. Kellogg School of Management, Chicago, and holds a bachelor's degree from Tufts University, Medford, MA.