Accountability, clarity, mission and influence — what to keep vs. let go when leading change in a legacy organization
Founded in 1922, USAA is a more than 14-million-member insurance and financial services company exclusively serving veterans and their families. Driven by transformative innovation and service, its latest focus is on the consumer experience, member value, and a 5-year $500-million Honor Through Action investment in careers and financial security for veterans. At the helm is its new CEO, Juan C. Andrade. With a background in journalism, national security, international affairs and drug policy for the federal government, and insurance, he joins Off the Rak to share insights from a diverse career, a mission-driven culture, and what it takes to lead change while protecting what matters.
About the Guest
Juan C. Andrade serves as the president and chief executive officer of USAA. He brings significant private and public sector experience in senior leadership roles across multiple global organizations and a strong track record of driving operational excellence, innovation and financial performance. Juan leads the Association with a deep commitment to serving the military community and their families.
USAA ranks among the most respected financial services organizations in the country. In 2026, it was listed No. 93 on the Fortune 500® and was ranked No. 26 on the Fortune’s 2026 World’s Most Admired Companies list. USAA has also been recognized as both a VETS Indexes 5-Star Employer and a Military Friendly® Employer every year since those programs began. Guided by its Mission, USAA directs the majority of its philanthropic efforts to initiatives that strengthen the military community. In 2025, the Association launched Honor Through Action, a five-year, $500 million commitment to advancing meaningful careers, financial security and overall well-being for the military community and their families through focused philanthropy, research-informed programs and targeted policy advocacy. Honor Through Action builds on USAA’s Face the Fight™ initiative to prevent veteran suicide.
Juan has served on USAA’s Board of Directors since 2020 and is also a member of USAA’s Federal Savings Bank Board of Directors. In his Board service, he contributes to key committees focused on member experience, risk, finance and technology.
Before joining USAA, Juan was the president and chief executive officer of Everest Group, Ltd., a global provider of reinsurance and insurance solutions. Prior to Everest, Juan held senior executive positions at Chubb, The Hartford and Progressive, leading businesses across domestic and international markets and delivering sustained operational excellence.
Beyond the private sector, Juan has a distinguished record of public service, with experience in national security, international affairs and drug enforcement. He has held key roles in the U.S. federal government’s Executive Branch, including the Office of the Secretary of Defense, the Drug Enforcement Administration and the White House Office of National Drug Control Policy. In recognition of his work in national security, he was awarded the Secretary of Defense Medal for Meritorious Civilian Service.
Juan is a leader in the global insurance industry, serving as a member of the Geneva Association, the international association of insurance companies and a leading industry think tank. He serves on the executive committee and the board of the American Property Casualty Insurance Association, the primary national trade association for the U.S. property and casualty insurance industry. Additionally, he serves on the American Red Cross Board of Governors and is a member of Business Roundtable and The Business Council, two select groups of CEOs from leading global companies who collaborate on issues shaping the global economy and business leadership.
He holds a bachelor’s degree in journalism from the University of Florida and was honored as a Distinguished Alumnus in 2018. Juan also holds a master’s degree in international economics and Latin American studies from the Johns Hopkins University School of Advanced International Studies. In 2023 and 2025, he was recognized by The Wall Street Journal as one of the World’s Most Influential Decision Makers.
