Before he was CEO of Communitech, Sheldon McCormick recruited Uber's first Canadian drivers from the back of taxi lines, eventually running a $100M P&L across multiple markets as GM of UberX in Canada. He then co-founded Properly, a proptech company that gained significant traction during the pandemic. He navigated a sharp market turn by executing a clear-eyed, non-traditional exit when conditions changed. He then spent two years as Founder and Partner at Tourmalet Partners, evaluating small family businesses with a view to wholly acquiring — work that gave him a ground-level view of exactly the pace, constraints, and decisions this audience faces every day. Drawing on this arc, Sheldon will share hard-won lessons on knowing when a strategy needs to change, staying close to the customers and successors who keep a business honest, and leading with clarity when the plan you built no longer fits the moment. For family enterprises and scaling businesses alike, navigating AI adoption and digital transformation is really the same challenge Sheldon has faced repeatedly: recognizing when the ground has moved, and having the discipline to move with it. What Attendees Will Take Away Product-market fit isn't permanent. A model can be sound and tested, then stop working when the market shifts. The skill is noticing early, not defending what used to work. Know which mode you're in: protecting what works, or experimenting to find what will. Confusing the two wastes time and capital, especially in an established business. The two miracle problem. Don't let ambitious change quietly require two independent things to succeed simultaneously. Naming both risks honestly up front prevents costly surprises later. Change doesn't always move at the pace you want it to. Sheldon's two trying to wholly acquire small family businesses taught him that deals – and generational transitions – often move slower than outsiders expect, and forcing the pace can cost you the opportunity entirely. Resilience means finding the responsible path, not the heroic one. When conditions change, strong leadership means a clear-eyed decision, not freezing or overreaching. About Sheldon McCormick Sheldon McCormick is the CEO of Communitech, bringing a rare mix of founder grit, scale-up execution, and national operator experience. He previously helped launch and scale Uber Canada across eight markets, overseeing a $100M P&L, before co-founding Properly, a venture-backed Canadian proptech company that he helped build and ultimately exit after seven colourful years. He also spent two years as Founder and Partner at Tourmalet Partners, evaluating small family businesses for acquisition, which gave him firsthand insight into the pace and realities family enterprises face when navigating change. With firsthand experience navigating hypergrowth, regulation, fundraising, and the realities of building from zero to one, Sheldon brings a deeply founder-centric lens to Communitech's next chapter in Waterloo Region.
Before he was CEO of Communitech, Sheldon McCormick recruited Uber's first Canadian drivers from the back of taxi lines, eventually running a $100M P&L across multiple markets as GM of UberX in Canada. He then co-founded Properly, a proptech company that gained significant traction during the pandemic. He navigated a sharp market turn by executing a clear-eyed, non-traditional exit when conditions changed. He then spent two years as Founder and Partner at Tourmalet Partners, evaluating small family businesses with a view to wholly acquiring — work that gave him a ground-level view of exactly the pace, constraints, and decisions this audience faces every day. Drawing on this arc, Sheldon will share hard-won lessons on knowing when a strategy needs to change, staying close to the customers and successors who keep a business honest, and leading with clarity when the plan you built no longer fits the moment. For family enterprises and scaling businesses alike, navigating AI adoption and digital transformation is really the same challenge Sheldon has faced repeatedly: recognizing when the ground has moved, and having the discipline to move with it. What Attendees Will Take Away
About Sheldon McCormick
Sheldon McCormick is the CEO of Communitech, bringing a rare mix of founder grit, scale-up execution, and national operator experience. He previously helped launch and scale Uber Canada across eight markets, overseeing a $100M P&L, before co-founding Properly, a venture-backed Canadian proptech company that he helped build and ultimately exit after seven colourful years. He also spent two years as Founder and Partner at Tourmalet Partners, evaluating small family businesses for acquisition, which gave him firsthand insight into the pace and realities family enterprises face when navigating change. With firsthand experience navigating hypergrowth, regulation, fundraising, and the realities of building from zero to one, Sheldon brings a deeply founder-centric lens to Communitech's next chapter in Waterloo Region.