VANCOUVER — When a Silicon Valley startup announced late last month that Toronto area roads would soon host a fleet of driverless delivery trucks, it came with news of an investment from Wittington Ventures. Founded in 2019, the venture capital firm is affiliated with the holding company of Canada’s billionaire Weston family, best known for its ownership of Loblaw, Canada’s largest grocery retailer, and Shoppers Drug Mart, its largest pharmacy.

The bet on self-driving-vehicle company Gatik was Wittington’s fifth investment, and its partners plan to add several more. Its $100-million venture fund puts money into tech startups in the spaces in which Loblaw operates, leaning on the chain’s expertise to identify investment opportunities, while trying to find solutions to some of its needs. And as Loblaw evolves from a traditional brick-and-mortar retailer into a digital juggernaut, a look at Wittington’s deals offers a glimpse of the retailer’s future.