DiMichele manages the Toronto Regional Real Estate Board (TRREB), North America’s largest local Realtor board with over 73,000 members. Regarded as one of the sharpest leaders in the organized real estate world, he strengthened his leadership bench in 2024 with the addition of Kevin Crigger as an associate CEO. DiMichele helped establish PropTx, TRREB’s MLS and technology services subsidiary, which the association expanded in 2024 as part of an effort to develop a provincewide database. He also serves as chair-elect of the Council of Multiple Listing Services.