Skeen's professional base has been the GTD class of what is now the IMSA WeatherTech SportsCar Championship, competing across the Pirelli World Challenge, Rolex Sports Car Series, Continental Tire Sports Car Challenge, WeatherTech SportsCar Championship and, in one season, the FIA World Endurance Championship.
His most prominent teams in IMSA have included Park Place Motorsports (Porsche 911 GT America), GB Autosport, Lone Star Racing, Stevenson Motorsports, Starworks Motorsport, Alegra Motorsports and Team Korthoff Motorsports.
In 2018 he shared Lone Star Racing's No. 80 Mercedes-AMG GT3 with Scott Heckert in the Pirelli World Challenge SprintX GT class, recording two pole positions and one win. They finished sixth in the standings.
The 2022 season with Team Korthoff Motorsports produced Skeen's best IMSA results: third place in GTD at the Daytona 24 Hours and second place in GTD at the Sebring 12 Hours. He also set the GTD pole position at the Sahlen's Six Hours of The Glen that year.
In 2020 Skeen joined the Trans-Am Series TA2 class with Stevens-Miller Racing and won the season opener at Sebring International Raceway, his only Trans-Am victory on record.
Skeen has appeared in NASCAR as a road course specialist on several occasions.
In 2012 he ran one race in the NASCAR K&N Pro Series West, driving the No. 31 Chevrolet for Richard Childress Racing at Miller Motorsports Park, finishing seventeenth after starting fifth.
In 2013 he made his Truck Series debut, driving the No. 6 Chevrolet Silverado for Sharp Gallaher Racing in the Chevrolet Silverado 250 at Canadian Tire Motorsport Park. He finished thirteenth after starting third. The event became notable for what happened after the race: Skeen's girlfriend Kelly Heaphy confronted Max Papis following a late-race contact incident, allegedly slapping him and dislocating his jaw. Heaphy was fined and suspended indefinitely by NASCAR; Skeen's crew chief was also fined.
In 2018 Skeen made his NASCAR Xfinity Series debut, driving the No. 15 Chevrolet Camaro for JD Motorsports at Watkins Glen International, finishing twenty-eighth and six laps down after starting twenty-fourth. He returned to the Truck Series in August 2020, joining NEMCO Motorsports for the Sunoco 159 at the Daytona International Speedway road course. His most recent Xfinity start was at Watkins Glen in 2024 for Jordan Anderson Racing in the No. 87 Chevrolet.
Skeen represents the career model of the North American GT3 professional: deeply embedded in endurance and sprint competition across a decade of IMSA competition, occasionally crossing into NASCAR on circuits that suit his road-racing background. His current programme with Triarsi Competizione in Ferrari machinery continues that focus.