The day after Rob Waters learned of his layoff from Google last year, he was encouraged to apply for a new role there as an AI sales specialist. Google soon offered him the position, with a six-figure salary.
Waters wasn’t sure he wanted to return. He’d grown frustrated with the bureaucracy at Google and how the reorganization that eliminated his team had been handled.
But walking away meant giving up about a few hundred thousand dollars in unvested equity.
“I killed myself working and dedicating myself, and then all I got to show for it was getting let go,” said the 42-year-old, who lives in San Francisco.
He’d also dreamed of starting his own company. The layoff, he said, “ripped the bandaid off.” Waters decided to bet on himself and pursue Kanawai AI, a startup he cofounded.
“All the equity that was unvested was gone,” he said. “I went from making very high six figures to zero.”
Rob Waters
Stock compensation has long given Big Tech workers a powerful incentive to stay put. Since the end of 2022, shares of Meta, Alphabet, Amazon, Apple, and Microsoft have all at least doubled.
But years of Big Tech layoffs have reminded some workers that their stock compensation isn’t guaranteed. Meanwhile, the AI boom has created another path to potential equity riches. And for some workers, years of gains on vested stock have given them the financial security to leave Big Tech on their own terms.
When Big Tech stock makes leaving easier
Julie Zhu, 29, had wanted to become a founder since she was 18 and said she’d developed a “love-hate relationship” with Apple, where she worked as a product designer. She was grateful for what she’d learned at the company but said it was a high-pressure, high-stress environment. She wanted more control over her work.
Still, Zhu wanted to make sure she could afford the risk of leaving. Her goal was to have three to five years of runway. Her Apple stock came in handy.
“I didn’t sell anything during my time at Apple, and Apple has been doing really well,” she said.
Last year, after nearly four years at Apple, Zhu resigned to focus on Odd One In, the artist collectible company she’d been building on the side. She said it felt like the right time, though leaving meant forfeiting the remaining quarter of her Apple stock grant that hadn’t yet vested.
Julie Zhu
Yousuf Imran also built up a financial cushion during roughly six years at Google, where his compensation included company stock. He set aside $350,000 for business and personal expenses before leaving in April to start an AI sales tools company. Imran said the potentially “life-changing” equity packages at companies like OpenAI and Anthropic shaped his decision.
“If the only way to get real upside in this AI moment is equity, at some point, you ask yourself whether the equity should be in your own company,” he said.
Dave Lewis also credited stock compensation for giving him the flexibility to consider career options outside Big Tech. Lewis, who spent more than a decade working at Google, Amazon, and Microsoft, said the wealth he’d accumulated from stock compensation gave him enough of a financial cushion to be selective after he was laid off by Microsoft last October.
With AI reshaping the tech industry, Lewis said he wanted his next role to position him for where he thought the industry was headed. In May, he joined Emberos, an AI startup, as head of partnerships.
Jacob Zinkula writes about how workers in tech and other industries are navigating their careers. Share your story with him by filling out this form, emailing him, or reaching out via Signal at jzinkula.29. Follow his work by clicking here.
With stock compensation, timing can be everything
For all its potential upside, stock compensation can leave workers’ finances exposed to luck and timing: of when they join the company, vesting schedule, stock performance, and their decisions to sell or hold. One former Meta employee got lucky: Meta’s shares had fallen sharply when he joined in 2022 and received a “boatload” of restricted stock units on the cheap. The stock then surged over the next few years.
Not everyone is as fortunate. A former Microsoft employee in her 60s said she still held a large amount of company stock when she lost her job last year after more than a decade there. She initially thought her savings and stock holdings might allow her to retire, but after Microsoft shares fell sharply, she began to question whether she could afford to.
The golden handcuffs only go so far
For all its complications, stock compensation remains one reason Big Tech is so appealing. A former Amazon employee said the company’s salary-and-stock compensation was lucrative and also felt more predictable than the bonus-heavy pay structure she had at her previous employer.
But even a predictable compensation package depends on keeping the job. After a few years at Amazon, she was laid off last year.
Even for workers who do retain their jobs, the financial incentives to stay only go so far. As Bushra Amiwala weighed whether to leave her sales associate role to run for Congress, she said she felt the pull of Big Tech’s so-called “golden handcuffs.” Staying at Google offered the salary, stock, and stability that could help her continue supporting her immigrant parents financially.
For Amiwala, the deciding question wasn’t whether she’d win the race — she ultimately left Google but lost the election — or what she’d give up financially by leaving Google. It was whether, five or 10 years later, she’d regret not taking the chance.
“For me, it was a no-brainer,” she said. “I knew I’d regret not doing it.”
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