On August 10, 2021, one brother gave the top job to the other. Mike Wessinger, who had run PointClickCare as founding CEO, moved to executive chair. Dave Wessinger, his co-founder and brother, became chief executive on September 1.
Dave described it as orderly succession and good governance. Mike said he was incredibly proud of what he had grown. It was a calm announcement for a company that began with something very small: a clinical documentation tool built for one long-term care facility in Mississauga, Ontario.
Over those years it chose a market most software firms avoided: care homes, where staff are stretched and records still lived on paper.
Nobody in that building was shopping for a platform. They needed to record what was happening to patients. The brothers were not a Silicon Valley pair. Both have undergraduate degrees from the University of Western Ontario, and Mike also started a separate software firm, Wescom Solutions, in 2000. The exact founding year varies by profile, but the company was already more than twenty years old when the handover came.
Over those years it chose a market most software firms avoided: care homes, where staff are stretched and records still lived on paper. Dave worked as chief operating officer and president before the top job. A board chair, Bill Dillane, stayed in the seat for more than twenty years, a rare kind of loyalty in a venture-backed company.
The outside money was patient too. Dragoneer invested in 2017 and 2018. In January 2021 Hellman & Friedman took a minority stake while the founders kept control, at a valuation reported as US$4B. By the time of the handover PointClickCare served more than 21,000 care providers and over 1,300 hospitals, with about 1,500 staff, most of them in Canada.
What almost nobody noticed in the announcement is how little drama it held. The founder who built the product stepped sideways into a role facing outward, and a brother who had spent decades on operations took the wheel. Dealroom puts the company at around US$5B in November 2026.
The lesson for a founder is about the end of the story, not the start. The brothers had one customer with a real problem and years of patience. And when it was time to change roles, they did it on a date they chose, in public, with the board still in place.