Kevin O'Brien

Worth knowing

He has run the commercial side of Aeroplan and led WeightWatchers in Canada and across every market outside North America, so he knows what it takes to sell a consumer brand at national scale and to take one across borders. He also writes early cheques into deep-technology B2B software. Founders bringing a consumer or health product to Canada, and technical founders raising a first round, should get in touch.

Story

Kevin started out as a Principal at Mercer Management Consulting, then built Diesel Think Tank, a marketing and advertising firm later purchased by Secor Group, where he went on to serve as Managing Partner. At Aeroplan and Aimia he moved through senior commercial roles to Chief Commercial Officer, negotiating partnerships including the 2015 Aeroplan tie-up with Toyota Canada. In 2017 he took over WeightWatchers Canada as President, later adding responsibility for all WeightWatchers markets outside North America, and stayed through 2023. He joined Travel Edge Network as Senior Vice President in 2024. An Ivey HBA from 1993, he returned to the school in 2020 to sit on an executive education panel on strategy, and now advises the DMZ, BioTwin and Harry Rosen from Toronto.

Highlights

• Founding Partner, The Group Ventures, Toronto early-stage B2B software VC
• Former Chief Commercial Officer, Aeroplan/Aimia
• President, WeightWatchers Canada; Head of International Markets, 2017-2023
• Advisory Board Member, Ivey Business School and Harry Rosen
• HBA 1993, Ivey Business School, University of Western Ontario