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Explore a provocative conference talk that challenges the traditional role of Chief Information Security Officers (CISOs) in the cybersecurity landscape. Delve into a thought-provoking discussion led by Alexander Romero, a CISO in the Department of Defense, and Steve Luczynski, a recently retired Air Force officer turned CISO. Examine the effectiveness of the CISO role over the past 20 years and question whether information security has improved because of or in spite of this position. Consider the projected $1 trillion global spending on information security in the next five years and its potential 100% failure rate. Gain insights from Romero's experience as a "Digital Services Expert" at the Defense Digital Service and his involvement in the government's first bug bounty program, Hack the Pentagon. Prepare for a speculative and potentially controversial exploration of the future of cybersecurity leadership, presented with a mix of humor and critical analysis.