Jean-Michel Lemieux of AI company Spellbook at Arlo, a restaurant he owns in Ottawa, on Friday.Jess Deeks/The Globe and Mail
Jean-Michel Lemieux charted a different course after serving as chief technology officer of Shopify Inc. He built a Strava-like app for boaters called SeaPeople, and also co-designed and built an award-winning catamaran that he raced across the Atlantic Ocean. His Ottawa restaurant, Arlo, made Canada’s 100 Best list three times.
Now, five years after leaving Shopify, Ottawa-based Mr. Lemieux has tacked back to familiar waters. He’s joined one of Canada’s fastest-growing tech companies, legal artificial-intelligence software vendor Spellbook.
This time, Mr. Lemieux is not taking the CTO title with the St. John’s-based company, incorporated as Dialog Enterprises Inc., but a position labelled “executive individual contributor.” “I didn’t want the CTO role because I felt it put me in a bit of a box,” Mr. Lemieux says. Employees have taken to calling him “executive skipper” since he started two weeks ago, he said.
It’s a new type of role that the 55-year-old Mr. Lemieux and Spellbook chief executive Scott Stevenson said is better suited to the realities of building AI-native companies. Those modern companies develop software at a more rapid pace than in the past and their bottlenecks are the speed of decision-making and co-ordination, they said.
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Mr. Lemieux, who invested in Spellbook and began advising the company last year, will build an “AI-first operating system” for the company. He will act as a cross-functional technical operator who will have his fingers in product, engineering, go-to-market activities and internal systems.
“The best way to hire an Olympic-class team is to find amazing people who are hard to come across, then build the job description that excites them,” Mr. Stevenson said. “We would have gladly made him CTO, but he had bigger ambitions and wanted more flexibility. He’s an incredibly versatile executive. We’re excited to see how this model works out.”
Mr. Lemieux has already built an agentic AI onboarding system for new employees – which he used himself – and sat in on sales calls and technology reviews. “These guys learn super quickly, it reminds me of the early Shopify days,” said Mr. Lemieux, who led sales at one point during his 6½-year stint at the company.
Mr. Lemieux, who was vice-president of engineering at online software pioneer Atlassian Corp. before joining Shopify, likened the state of the legal technology market to where e-commerce software was in the first half of the 2010s, calling it “a knife fight.” Shopify ultimately emerged from that period as the leading provider of direct-to-consumer commerce software, as Amazon.com Inc. and others became dominant marketplaces.
Spellbook, backed by Khosla Ventures, Thomson Reuters Ventures, Inovia Capital and others, was an early entrant in the generative AI field, launching its tool for lawyers in 2022. The 200-person company has emerged as a front-runner in a nascent market. It’s on pace to surpass US$100-million in annualized revenues this year.
Spellbook has more than 4,500 corporate customers, including Nestlé SA, eBay Inc. and Franklin Templeton. Their lawyers use Spellbook’s AI co-pilot, powered by large language models, including OpenAI’s GPT-5, to automatically draft, edit and review legal contracts within Microsoft Word.
Rivals Harvey and Legora have hired celebrity pitchmen, while Anthropic’s recent upgrade adding tools and functionality for lawyers to its Claude platform has sparked fears that legal software providers could be displaced by their own customers fashioning bespoke solutions.
The higher profile for the legal AI space has helped drive overall awareness and urgency among lawyers that they should adopt the technology, Mr. Stevenson said.
“Every time that OpenAI or Anthropic has hyped up lawyers, our funnel has grown,” he said, noting that Spellbook doubled its sales meetings to 400 a week in March after Claude introduced its tools for lawyers. “That ultimately is helping us. Any company in our position, though, must relentlessly provide additional value on top of what you can do with Claude.“
Mr. Lemieux said he believed Claude would appeal more to technically minded customers, while Spellbook will “sell to the in-house lawyers who want an out-of-the-box solution that works for all their workflows. That’s the bet I’m making.”
That said, “there’s a lot of question marks,” Mr. Lemieux added. “No one is thinking that Anthropic can’t do some crazy things. I’m joining because it’s not a safe bet. We know lawyers are downloading and trying Claude. We’ve got to win those on merit.”