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Welcome to another episode of the Business Leaders of America Podcast. In this episode, we sit down with Darrick “DJ” Johnson, a former collegiate and professional football player who successfully transitioned into the world of technology and entrepreneurship. Today, DJ serves as the Director of Enterprise Sales at Microsoft and is the Founder of Sherpa, an AI-powered sports intelligence platform. Growing up in Compton, California, he overcame tremendous challenges to earn his degree from Georgetown University and later rise into leadership roles at global tech giants including Apple, Dell, and Microsoft.
DJ shares his journey from the football field to the world of technology, reflecting on his experiences managing multi-million-dollar AI and cloud deals and the lessons he’s learned along the way. He dives into the inspiration behind founding Sherpa, his new AI-powered sports intelligence platform, explaining how it unifies the athlete lifecycle from NIL deals and pro contracts to scouting and recruiting in ways previous tools haven’t.
This episode is a fascinating look at the intersection of sports, technology, and entrepreneurship, and how DJ is helping athletes and those who represent them maximize value on and off the field.
Notable Awards and Recognitions
• Founder of Sherpa, an AI-driven platform designed to streamline operations and empower organizations with advanced decision-making tools.
• Director of Enterprise Sales at Microsoft, where he leads enterprise-level cloud and digital transformation initiatives for some of the world’s largest organizations.
• Held leadership roles at Apple and Dell, driving growth and innovation across global technology markets.
• Recognized for his ability to bridge the gap between sports, leadership, and technology, inspiring the next generation of entrepreneurs and executives.
• Former professional football player, bringing the discipline, resilience, and leadership skills from the field into the corporate world.
How to connect with Darrick “DJ” Johnson
• https://sherpasports.ai/
• https://sherpaclouds.com/
• https://www.linkedin.com/in/darrick-dj-johnson-li/
• https://www.instagram.com/deejack24x8/
• https://www.instagram.com/sherpaclouds?igsh=MTN3d3Jsa3Q0eWRqaA%3D%3D&utm_source=qr
• https://x.com/sherpasportsai?s=21
• https://www.linkedin.com/company/sherpa-clouds-inc/
Show Notes
[1:52] DJ shares his journey from playing professional football to becoming Director of Enterprise Sales in Cloud & AI at Microsoft, and how he made the transition from the field to the world of tech and AI.
[5:19] The biggest lessons DJ learned at Microsoft while managing multi-million-dollar deals and helping major organizations scale with AI and cloud solutions.
[11:08] Why mentoring and advocating for diversity in STEM is such an important part of his mission and how he works to encourage greater representation in tech.
[18:33] The inspiration behind founding Sherpa, his new AI-powered sports intelligence platform, and explains the market gap it aims to fill.
[22:10] How Sherpa unifies the entire athlete lifecycle from NIL deals to pro contracts to scouting and recruiting in ways that previous tools haven’t achieved.
[28:19] The why he chose to build Sherpa on Microsoft and AWS, highlighting how enterprise-grade tech supports the platform’s scale and security.
[30:41] Sports teams, agencies, and organizations that have started using Sherpa and the early feedback the platform has received.
[34:56] DJ shares the best ways for listeners to learn more about Sherpa and how they can connect with him directly.
[36:16] Advice for anyone launching a new AI-driven product, sharing key insights from his own experience building Sherpa.
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