Harvey’s CEO told Business Insider he’s growing his $5 billion legal AI startup by focusing on two things: regular calendar audits and hands-on hiring.
Winston Weinberg, who cofounded Harvey three years ago, said in an interview on the sidelines of TechLaw.Fest in Singapore in September that as Harvey doubles revenue roughly every six months, the demands of running the company change just as quickly.
“When that happens structurally, you just get all of this pressure as the CEO,” he told Business Insider. “The only way to relieve that pressure is to completely level up and change how you operate,” he added.
To keep up, he said he conducts what he calls a “calendar audit,” combing through how he spends his time and deciding what to drop, what to delegate, and what to take on personally.
Weinberg said his aim is to automate himself out of daily operations so he can focus on what he sees as a CEO’s three core jobs: recruiting, product, and customers.
“Every founder wants this — you’re trying to automate yourself away,” he said.
“I want to be able to feel that when something goes wrong or something is the No. 1 priority, that I can focus all of my time on that, and the rest of the company is humming,” he added.
Hiring is the one area Weinberg won’t delegate, especially in new offices. He said he wants to be involved with the first hires whenever Harvey opens a new office.
The company said its APAC office in Sydney opened last month. It will hire about 15 people there this year, with plans to increase its head count further after that.
Those first hires really matter because they are “going to go out and hire more people,” he said.
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He added that in some cases, he has tapped existing Harvey employees with local roots to lead new offices — like the company’s head of Australia, who was born and raised there.
Growing at a startup
While larger AI players like OpenAI and Anthropic can outspend him, Weinberg said Harvey’s edge comes from empowering leaders early.
“What we can do is we definitely promote junior talent, and you will have just way more ownership at our company,” he said of the 350-person company.
“There are folks that have never managed people in their entire careers that are now managing 20 people,” he added.
Some tech leaders have also echoed that it’s wiser to work for startups over big companies.
Y Combinator cofounder Paul Graham said on X last year that while working for big companies might be “safer,” the connections forged with startup colleagues can cue up future success.
“In 10 years they’ll be running everything,” Graham wrote of startup employees, “even if the startup tanks.”
