Derek is a seasoned professional with a diverse career spanning various industries, including financial services, sports media, logistics, and blue-collar staffing. Over the last seven years, he has demonstrated his leadership by scaling two- and three-sided marketplaces from inception to multi-billion dollar enterprises. Notable highlights include his work at Deloitte Transfer Pricing, where he provided economic and tax consulting services to multinational financial services companies. At ESPN Digital Media, Derek played a pivotal role in strategic and financial planning, contributing to the launch of ESPN's first direct-to-consumer streaming service.

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He also made significant contributions at Uber Eats, overseeing the launch of the first Uber Eats territory in the US and later managing West Coast operations and competitive strategy. His experience at Workrise (formerly RigUp) involved leading diverse teams in staffing operations, oil field logistics, strategy and planning, human resources, and financial operations.