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 28 years, he has been a key industry figure, 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 in 2017 after two decades with a prominent multi-sport and marketing agency.