Keith's baseball journey began with an outstanding amateur career, highlighted by multiple summer championships with the esteemed East Cobb Baseball program. Drafted 59th overall in the 1990 MLB Amateur Draft, he chose to pursue college, where he earned All-ACC honors as a shortstop at the University of North Carolina and became an all-star while winning a Cape Cod championship. After being drafted by the Colorado Rockies, Keith spent five seasons in their organization before transitioning to a successful career as an MLBPA-certified agent in 1998. Over the past 26 years, he has been a key figure in the industry, serving on the inaugural MLBPA Player Agent Advisory Committee (2011–2012), advising numerous first-round draft selections, navigating 25 salary arbitration cases, and securing record-breaking contracts. His clients have achieved recognition across all major awards. Keith joined Vanguard after two decades with a prominent multi-sport and marketing agency.