In this episode of “Tipping Spears,” we sit down with William Bender, a retired three-star general, former Chief Information Officer of the United States Air Force, seasoned board director, and technology executive whose career bridges military command, enterprise IT modernization, and private-sector growth. As Air Force CIO, he oversaw a $17 billion IT portfolio and a 54,000-person workforce while launching foundational roles such as Chief Information Security Officer, Chief Data Officer, and Chief Innovation Officer - changes that reshaped how the Department of Defense approaches cybersecurity, data, and innovation. He also helped establish the Air Force Innovation Unit, which evolved into today’s Defense Innovation Unit under the Office of the Secretary of Defense.
Following 35 years of service, Bender transitioned into the private sector, serving as Senior Vice President at Leidos, where he led Government Relations and Customer Account Management during a period of substantial growth. Today, he serves as a Principal at Deep Water Point & Associates, and sits on multiple technology and cybersecurity boards, including AFCEA International (where he previously served as Board Chair), Tangram Flex, GrammaTech, Anametric, and Vislink. Across these roles, he advises companies at the intersection of data, cybersecurity, defense, and emerging technology.
Our conversation explores the arc of his leadership journey - from early catalysts that shaped his decision to serve, to commanding global operations, to driving IT modernization during wartime. He shares candid insights on leading large bureaucratic institutions through disruptive change, standing up new innovation structures inside the Pentagon, and managing strategic risk in an era defined by cyber threats, AI acceleration, and geopolitical competition. We also examine the realities of industry-government collaboration, the barriers that must be addressed to make it effective, and what today’s technology leaders must prioritize to remain resilient and mission-focused.
This episode is a masterclass in strategic leadership - how to build institutions that endure, modernize at scale, and navigate uncertainty without losing sight of mission!
Guest Bio:
Bill Bender is a seasoned board member, tech industry executive, former USAF CIO, and retired three-star general with extensive expertise in IT, cybersecurity, and governance. As CIO, he oversaw a $17B IT spend and a 54,000-person workforce. At Leidos, his leadership of Government Relations & Customer Account Management supported growth from $10B to $15B.
As a prominent technology leader, Bender currently serves on multiple boards, including Tangram Flex, GrammaTech, Anametric, Vislink, and formerly served as Board Chair for AFCEA International. He is a strategic growth advisor to Keeper Technology, focused on data management and storage solutions, to IT Cadre, focused on enterprise data visualization, and to numerous other data-centric and cybersecurity companies. He is a Principal with Deep Water Point & Associates, providing consulting services and thought leadership.
Previously, as CIO of the USAF, he spearheaded IT modernization and cybersecurity, establishing the first roles for CISO, CDO, and Chief Innovation Officer within the Department of Defense. He also envisioned a first of its kind initiative to leverage the Silicon Valley entrepreneurial and innovation ecosystem, establishing the Air Force Innovation Unit, which led to today’s Defense Innovation Unit with the Office of the Secretary of Defense. He also developed key initiatives like Agile Software Factory and USAF’s Cloud First strategy.
As a USAF officer, he served as Deputy Chief at the Office of Security Cooperation in Baghdad, leading the development and implementation of foreign military sales to Iraq. He served as Commander of the USAF Expeditionary Center and dual-hatted as AMC Numbered Air Force Commander, responsible for all enroute operations of sustainment. He also led communications training and global deployment efforts for 21,000 personnel. Throughout his distinguished military career, he held multiple global leadership roles including, Director of Warfighting Integration, and as Commander of the 86th Airlift Wing. He has also held key positions on various executive and advisory boards, including: AT&T, Leidos, Samsung, Cylance, Symantec, Tanium, Dun & Bradstreet, and Brown University.
About the Podcast:
Tipping Spears with Hannah Becker dives deep into the stories of the people shaping cyber, defense, and national security. Through thought-provoking conversations, we uncover the career journeys, lessons learned, and personal insights of leaders and innovators in these mission-critical fields. Discover emerging trends, cutting-edge strategies, and the human side of the challenges shaping our future. Learn more at: www.hannahebecker.com/podcast
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