Ex-Windows boss who tried to save the Start Menu now Shopify tech wizard

Time to make e-commerce great again instead?

Mikhail Parakhin, the former Windows boss who pledged to "make Start Menu great again" before departing Microsoft shortly after, has popped up as CTO of e-commerce outfit Shopify.

According to Shopify, "he led Microsoft's AI advancement, building consumer and enterprise-facing products like Copilot," and the company wants his smarts "not just in ML and AI, but in everything we're building to make commerce better for everyone."

Parakhin is also notorious for being outspoken. Given the reins at Microsoft, the engineer took one look at the Windows desktop and did not like what he saw. He took exception to some of the Start Menu functionality in Windows, replying to one complainant that it "annoys the hell out of me, too" and promising "to make Start Menu great again."

Parakhin's openness and willingness to engage were a breath of fresh air compared to certain notoriously secretive factions within Microsoft. In March, Parakhin was part of a reshuffle that resulted in him reporting to new Microsoft hire and DeepMind co-founder Mustafa Suleyman.

Shortly after, Parakhin was on his way "to explore new roles."

Since his stint as the head of Microsoft Bing, Parakhin has turned up in several AI businesses, including as an advisory board member for Perplexity. According to Shopify president Harley Finkelstein, Parakhin's hiring as CTO was a "huge win." Finkelstein lavished praise on the new CTO, saying: "Mikhail is exceptional when it comes to engineering, machine learning, search, and AI."

Shopify's previous CTO was Allan Leinwand, who departed at the beginning of 2023, leaving CEO Tobias Lütke to fill the role until Parakhin's arrival. Lütke described himself as "thrilled" to be working with Parakhin, saying: "He's a brilliant technologist, who I've deeply admired for years. Deep expertise in ML, AI, and search at huge scale."

Shopify turned a profit in 2023 and celebrated by cutting staff and raising prices. Prices have continued to rise in 2024.

In addition to his time at Microsoft, Parakhin was CTO at Yandex, a Russian search engine, between 2015 and 2019.

Parakhin's arrival at Shopify coincides with reports that buy now, pay later firm Klarna plans to eject almost half of its employees in the coming years thanks to greater use of AI. ®

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