Oliver resides in Brookeville, MD where he and his wife and son Will operate their ESP Farm. He is a United States Equestrian Federation “R” Jumper Judge and is also an FEI “I” Jumper Judge. He maintains a busy judging schedule that has included the Royal Winter Fair, Washington International, Hampton Classic, Vermont Summer Festival, Ocala Winter Circuit, Indio Desert Circuit, KY Spring and Summer Shows along with two USET Pan American Games Trials and the 1996 USET Olympic Trials.

Oliver has managed such shows as the Capital Challenge Horse Show, Legacy Cup, St. Christopher’s, Wachovia Jumper Classic at Beacon Hill, Columbia Benefit Grand Prix, Great Meadow Invitational, and the Syracuse Invitational Sport Horse Tournament.

Along with his management and judging duties Oliver announces a number of major horse shows such as the Winter Equestrian Festival, Washington International, USEF Pony Finals, Ocala Winter Circuit, Keswick, KY Summer, Lexington Spring Premier, and Upperville. His Television duties have included commentating for CBS, OLN, the BBC, Fox Sports, Prime Sports Network, MSG Network, and Yorkshire Television.

Oliver is the Chairman of the USHJA Zone III Jumper Committee, a past president of the Maryland Horse Shows Association and a member of the Board of the American Hunter & Jumper Foundation.