No one is thinking about your career as much as you are. You have to speak up and ask for things.
Cathy Engelbert on learned career lessons.
Speaker
Cathy Engelbert
In July of 2019, Cathy Engelbert was named the first-ever Commissioner of the Women’s National Basketball Association (WNBA) and is charged with elevating the sport of women's basketball and leading a multi-dimensional business transformation. Stepping into the role of WNBA Commissioner, Cathy executed a historic player-first Collective Bargaining Agreement in 2020 which tripled the pay of top players and provided an array of progressive benefits. She has built and socialized a new economic framework to drive league growth and stakeholder success. Cathy led the longest tenured women’s professional sports league in the U.S. through its 25th anniversary season and through the COVID-19 pandemic over her first two seasons at the helm. Cathy then raised $75M capital from outside investors to fund league transformation projects. In 2024, Cathy established the WNBA as a premier sports and media property by finalizing a historic set of media rights agreements that has significantly raised the bar for women's sports. Also, she led the league through a record setting season for viewership, attendance and social media reach, resulting in being named the Fastest Growing Brand of 2024 by Morning Consult and Fast Company's #4 Most Innovative Company of 2025.Prior to the WNBA, Cathy retired as the CEO of Deloitte in June of 2019, after 33 years with the firm. Elected as Deloitte CEO in 2015, she was the first woman CEO in the history of a Big Four professional services firm. In her role as CEO of Deloitte, Cathy led the largest accounting and consulting organization in the United States with more than 100,000 professionals. Cathy is a member of the Board of Directors of McDonald’s Corporation, Royalty Pharma, and the USGA Executive Committee. She also serves as the Vice Chair of the Partnership for New York City and is member of the Business Council, Council on the Foreign Relations, and Catalyst, a global non-profit organization that promotes inclusive workplaces for women. She has been listed as one of Fortune’s Most Powerful Women for four consecutive years, was ranked on Glassdoor’s annual Employees’ Choice Awards honoring the 100 Highest Rated CEOs, and is one of Fast Company magazine’s Most Productive People. In 2021, Engelbert was listed on the Forbes’ ‘50 Over 50’ list and Adweek’s ’40 Women to Watch’. Cathy received a Bachelor of Science degree in Business and Economics (Accounting) from Lehigh University. She has two children—earning her the recognition as one of Working Mother magazine’s 50 Most Powerful Moms for three years.
Moderator
Debra A. Cafaro
Debra A. Cafaro is the Chairman of the Board and Chief Executive Officer of Ventas, Inc., an S&P 500 company focused on the longevity economy and the world’s second largest owner of senior housing. With an enterprise value exceeding $50 billion, Ventas owns approximately 1,400 properties serving a large and growing aging population, including more than 850 senior housing communities that are home to over 90,000 residents. The Ventas portfolio also includes outpatient medical buildings, research centers and healthcare facilities. A recognized industry leader, Cafaro set and oversaw the execution of a long-term strategy that has driven Ventas’s market capitalization from $200 million when her leadership began in 1999 to nearly $40 billion in 2025. The Company’s annualized total shareholder return (TSR) has approximated 19 percent since the beginning of 2000.* Widely acclaimed for her strategic vision and enduring business success, Cafaro has received multiple professional recognitions, including being named: one of the Top 100 Best-Performing CEOs in the World for six consecutive years (Harvard Business Review); one of the 100 Most Influential People in Healthcare six times (Modern Healthcare); and one of the Top 50 Women in World Business (Financial Times). To honor her contributions, she has received the Order of Lincoln, Illinois’ highest honor for professional achievement and public service; the Visionary Award for Strategic Leadership from Women Corporate Directors, the preeminent organization of women corporate directors globally; and the Industry Leadership Award from Nareit. In addition to her work at Ventas, Cafaro is broadly engaged across business, public policy, academic, sports and non-profit sectors. Cafaro is a past Chair of the Real Estate Roundtable, a public policy organization that brings together leaders of the nation’s top real estate firms on key national policy issues; Nareit, the worldwide voice for listed real estate companies; and the Economic Club of Chicago. She serves on the Boards of The PNC Financial Services Group, Inc. (NYSE: PNC), The University of Chicago and the Civic Committee and the Commercial Club of Chicago. She is a member of the American Academy of Arts & Sciences and the Business Council. A lifelong sports fan, Cafaro is an owner of the MLB Baltimore Orioles, the NHL Pittsburgh Penguins and the NWSL Chicago Stars FC. Cafaro is deeply committed to creating opportunities through education and promoting civil discourse on important public issues. At the University of Chicago Law School, where she obtained her law degree, Cafaro established the Cafaro Scholars program, which provided over 20 full scholarships to high potential students whose parents did not attend college; and supports the Constitutional Law Institute, a nonpartisan, authoritative leader in research and scholarship on important constitutional issues. Before joining Ventas, Cafaro was President of an NYSE-listed apartment company, a practicing lawyer and a U.S. Court of Appeals judicial clerk. She received her J.D. cum laude from the University of Chicago Law School, where she was named its 2011 Distinguished Alumna, and her B.A. magna cum laude from the University of Notre Dame. She is married and has two children.
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