Bold Commerce was founded in 2012 by Jay Myers, Yvan Boisjoli, Stefan Doussis, and Eric Boisjoli in Winnipeg, Manitoba. They started by building Shopify apps — their Bold Subscriptions and Bold Upsell apps became some of the most popular on Shopify’s App Store, generating millions in merchant revenue.
The company pivoted to enterprise in 2020 with Bold Checkout, a headless checkout solution that brands can embed anywhere — websites, mobile apps, in-store kiosks, social media, IoT devices, or even chatbots. The idea is that checkout shouldn’t be locked to one storefront; it should work wherever customers want to buy.
Bold raised $38 million in total funding, with investors including OMERS Ventures and Round13 Capital. The company’s pivot from Shopify apps to enterprise infrastructure was a significant strategic shift that targeted much larger deal sizes.
Bold’s checkout APIs handle cart management, promotions, shipping calculations, tax, and payment orchestration. Brands can customize every step of the checkout flow — adding upsells, bundles, loyalty redemptions, and custom fields — without being constrained by platform limitations.
The subscription platform supports physical product subscriptions, digital memberships, and curated box models. Its price rules engine lets merchants offer subscriber discounts, build-a-box configurations, and flexible delivery schedules. Bold Commerce serves enterprise clients including Staples, Vera Bradley, and Harry Rosen, and employs around 300 people primarily in Winnipeg.
