About Derrick R. Pledger

Veteran, C-Suite Executive, and Author of Multiple Books.

Derrick specializes in digital transformation and innovation, empowering individuals, teams, and organizations with strategies for resilience, ambition, and success in corporate and entrepreneurial spaces.

Derrick is a US Army combat veteran, technology executive, digital strategist, and author of multiple books—one of which was co-written with Curtis “50 Cent” Jackson. He ran a multi-million dollar export business in his late twenties and become a Fortune 500 Chief Information Officer (CIO) by the age of forty. He is extremely passionate about “democratizing” what it takes to be successful via sharing insights and behaviors that help corporate employees, entrepreneurs, and teams achieve upward mobility and desired outcomes.

He is currently the Chief Digital and Information Officer (CDIO) at Maximus Inc. where he focuses on driving technology strategy, delivery operations, and digital modernization activities for the organization. As an industry leader with over 20 years of experience, Derrick’s technical expertise spans a wide range of areas, including systems integration, automation, cloud and edge computing, artificial intelligence, IT delivery governance, data analytics, and end-to-end solution development. Prior to joining Maximus, Derrick was the Chief Information Officer at Leidos, where he was responsible for executing digital and enterprise strategies in support of worldwide IT delivery operations. While there, he oversaw a global delivery team that supported a $15 billion corporation with more than 48,000 employees.

As a technologist and high-performance advisor, Derrick works with individuals, teams, and organizations to bring the best out of people through strategic intent, discipline, and “riding the tide of failure” to reach personal, corporate, or entrepreneurial objectives.  He is also a partner at 500 Pound Media, a content creation and digital media company focused on personal performance and achievement.