TORONTO — Canada’s biggest tech company is losing one of its key leaders, as Shopify COO Kaz Nejatian leaves to lead San Francisco-based Opendoor.

Nejatian, a former lawyer and fintech founder, has risen rapidly through Shopify’s executive ranks at a time when the Ottawa-headquartered firm has grown its revenues substantially and significantly overhauled its operations and culture. He will become Opendoor’s CEO at a tumultuous time for the online real estate firm, which became a meme stock and lost its last boss amid pressure from investors.

Nejatian joined Shopify from Facebook in September 2019 to head the commerce company’s financial services group, responsible for its lucrative payment processing feature. He was quickly promoted to vice-president of Shopify’s merchant solutions business, which generates the majority of the firm’s revenues via fees for services like shipping and financing. During his time in the job, Shopify launched several new tools, including ones that help store operators find and message customers.

In September 2022, Nejatian was named Shopify’s COO, taking over from long-tenured leader Toby Shannan. The change came amid a much wider shuffle of the firm’s top ranks during the pandemic, with only CEO Tobi Lütke and president Harley Finkelstein remaining in their previous roles.

Nejatian became one of Shopify’s public faces, speaking at conferences, on industry podcasts and in media interviews about the firm’s strategy and operations.

“Our job is to take the things that suck for entrepreneurs, and make them not suck,”
he said at The Logic Summit in June 2023. “It’s [to] take the advantage away from the big and give it to the small.” Initially used by upstart direct-to-consumer brands, Shopify has in recent years courted larger clients, including by letting them use its tools à la carte. 

Shopify declined to make Nejatian available for an interview on Thursday. The company did not immediately announce a replacement COO. Shopify spokesperson Ben McConaghy said Lütke will “stay focused on product and the big picture,” and cited the “deep leadership experience” of the firm’s executive team. Lütke has periodically retaken control of the firm’s product teams over its history.

Nejatian built “products that matter” and made “merchant services a core part of Shopify,” McConaghy said. He also helped lead Shopify’s big generative AI push, which included store assistant Sidekick, product listing suggestions and photo-editing tools.

Some former Shopify employees previously told The Logic that the firm’s culture changed for the worse after Nejatian became COO. They said the firm’s leadership became less open to staff feedback and discouraged internal discussion of political issues and contentious right-wing merchants like Breitbart and Libs of TikTok. Shopify also shut down its Build Native and Build Black programs that supported entrepreneurs from underrepresented communities, which had been under Nejatian’s purview.

Nejatian—who was based in the Bahamas, according to a February 2024 regulatory filing—was one of Shopify’s best-paid executives, with a base salary of US$800,000 last year. Shopify also awarded him US$75 million in restricted stock units and options in December 2023, although much of that has yet to vest.

Opendoor’s stock traded up as much as 78.2 per cent on Thursday following news of Nejatian’s appointment. In addition to the new CEO, the firm announced that co-founders Keith Rabois and Eric Wu would be rejoining the board. Nejatian brings “a founder’s brain” to Opendoor, which will become “an AI-first company,” new chairman Rabois said in a statement.

Former Opendoor CEO Carrie Wheeler resigned in August after pressure from investors on social media led by Eric Jackson, president of EMJ Capital, a Toronto-based investment manager. They also helped turn it into a meme stock, with the share price already up nearly 1,100 per cent from its late-June low through Wednesday.

Nejatian framed his move to Opendoor in societal terms, claiming in an X post that it could be a firm that “empowers the promise of the West to be unlocked in the ways it was always intended.” The company buys houses from owners, then resells them, generating revenue from the difference in price. It also lets users work with real estate agents. Under Nejatian, Opendoor will use AI to simplify the process of buying and selling homes and create “personalized pathways to ownership,” he said. 

In the short-term, Opendoor will give Nejatian US$15 million in cash and US$15 million in stock for forfeiting some of his compensation at Shopify. He also stands to benefit significantly if the firm’s stock price keeps rising. In a regulatory filing, Opendoor disclosed it could award Nejatian nearly 81.8 million shares over five years, with the full total vesting if the share price hits US$33. That translates to a US$2.7-billion stake.