Jean-Michel Lemieux missed building things with people.
The former chief technology officer at Shopify served on boards and dabbled in VC work, yet said that leadership alone left him too far removed from the work.
“I’m in these board meetings, and it feels like I’m a coach of a pro team, but I can’t see them play the game,” Lemieux, 54, said.
He said he loves the energy of “hands on keyboard.” So, these days, he’s working at Spellbook, which makes an AI copilot for lawyers. With the title “executive individual contributor,” he’s able to both lead and build.
“I love that adrenaline,” he said.
For Lemieux and executives like him, going back to software development isn’t only about revisiting an old passion. AI is transforming software development so quickly that some tech leaders are choosing to spend less time managing and more time building.
Back in the trenches
Reza Khadjavi feels the same urgency to build as the CEO of Motion, which created an “AI coworker” for marketers.
A couple of years ago, he began spending more time trying to understand AI and became “really fired up” because he said once-in-a-generation technological changes create enormous opportunities. At the same time, Khadjavi was also terrified, thinking, “If I don’t go into the weeds on this stuff, the company might die.”
So, while he hadn’t written a line of code in about a decade, Khadjavi bought a Mac mini and loaded it with an AI agent to help him research various tasks.
Eventually, Khadjavi shared the agent with others at his Toronto company, which has about 80 people. “It just started taking off internally,” he said, as staffers began asking the agent questions for their own work.
The experience “really changed my perspective of what it means to be a leader at a technology company,” Khadjavi said. He said it became clear that the conventional wisdom that leaders had to delegate and focus on setting a vision was becoming outmoded. That meant that at times, Khadjavi could act more like an individual contributor.
Working on the AI agent allowed him to feel like, ”OK, I spent some time, I built something, and that thing is useful to the rest of the team.”
Staying close to the work
After leaving his role as an engineering manager at Meta in May, Robert Sweeney looked for jobs in and out of leadership, on the condition that any management roles would allow him to spend at least 30% of his time building software.
Sweeney landed at Citizen Health, a healthtech company that helps patients with rare diseases share their medical records to accelerate research. Sweeney now spends half his time managing and half building software.
Working alongside engineers has convinced him that leaders need to stay close to the quickly evolving work.
“I felt like I couldn’t be a pure manager anymore, even if I wanted to, because I couldn’t understand the work that they were doing,” he said.
“How can a director or a senior manager even hold the engineering team accountable at all if he has no concept of what it takes to build the software?” Sweeney said.
The risk of getting too hands-on
Not every executive thinks getting back to building is the right move. Sameer Ranjan, chief technology officer at the Dallas AI startup Catenate, said he still enjoys tinkering with software, but believes his time is better spent guiding the firm’s direction than cranking out code.
“I left that chair so that somebody else can come and sit there,” he said.
One risk for execs who do rank-and-file work is getting so caught up in the details that they lose sight of the broader business. That’s something that Lemieux, at Spellbook, said he’s guarding against.
“The failure mode of this role is: I end up doing everything,” he said. To prevent that, Lemieux said he limits where he gets involved by looking for “the big boulder that I’ve got to move,” and when he does drop into a project, he lets the team know he might only be involved for a couple of months.
Lemieux views his job as temporary help on a project, a bit like a Navy SEAL: “Coming in, landing, making sure things are in a good spot.”
His role, he said, is to improve the team by working with them to improve the product. This way, when Lemieux moves to another area of the company, the team is left with tools or approaches they can continue to use, he said.
Lemieux said he arrives on a project ready to learn and makes clear that he’s not an auditor. “I’m not here to just whisper to the CEO all the time and tell him everything that’s going on,” Lemieux said. “There’s a big trust factor here.”
He said he tries to show up humbly. That might mean fixing bugs or writing the first draft of a press release. “I’m not just there to tell them what to do, but I’m there to do it with them,” Lemieux said.
He also reads the code and project docs to get up to speed. “I can’t come in as a pointy-headed manager,” Lemieux said. “I’ll do the homework to understand things deeply enough that I’m not a burden on the team.”
Ultimately, he said, working this way is appealing in part because, beyond being a VC or a board member, there is no widely known career path for builders like himself.
Lemieux said his goal is to help the staffers he works with grow faster and do more than they think they can. He believes working alongside them as an individual contributor — not solely managing them — makes that possible.
“Our bet is the company could be five times better than it would be without doing this,” Lemieux said.
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