In 2010, Kirk co-founded Wave, and has since guided the company to 400,000 active small businesses registered, 260+ people on the Wave team, and over $100 million in funding raised from investors around the world. In 2019, he and wave were named Most Admired CEO and Most Admired Corporate Culture by Waterstone. Wave was acquired in June 2019 by H&R Block for over $537M – the 7th largest tech exit in Canada since 2001. Under Kirk, Wave has won numerous awards for leadership, culture, and innovation, including the Deloitte Fast 50, the KPMG Fintech 100, and Great Place to Work Canada. In addition, Kirk has served as advisor to the Next 36, and provides mentorship to young entrepreneurs and startup visionaries.