[10][11] Weston succeeded his father to become the executive chairman of Loblaw Companies Limited in October 2006.

In the statement, Weston is quoted as saying "this sort of behaviour is wrong and has no place in our business or Canada's grocery industry," and that "this should never have happened.

[19] In June 2020, Weston confirmed the cancellation of an hourly CA$2.00 wage premium to Loblaw workers, which received criticism from then Unifor President Jerry Dias.

The premium was paid to low-wage grocery store workers, who were deemed "essential" and required to attend work while much of Canada was shut down in response to the COVID-19 pandemic.

[22] On April 18, 2023, it was announced that Weston would step down as president of Loblaw, to be succeeded by Danish retail veteran Per Bank in 2024.

[23] In 2005, Weston married Alexandra Schmidt, granddaughter of businessman Thomas J. Bata and his wife, Sonja.