In 2024, McCaskill became chief operating officer and general counsel for North Carolina-based Canopy Realtor Association, its MLS subsidiary and its housing foundation. McCaskill provides legal guidance and compliance support and oversees day-to-day operations, strategy development and innovation for the group, which ranks as the U.S.’s 15th largest local Realtor association and runs the nation’s 17th largest MLS. A licensed Realtor, McCaskill previously served as Canopy’s assistant general counsel and as vice president of member services.