Big Tech stock compensation has long acted like golden handcuffs. It can keep workers in place with the promise of future wealth, but layoffs and the AI boom are changing the math.
Rob Waters learned that firsthand after Google laid him off last year. The next day, he was encouraged to apply for a new role there as an AI sales specialist, with a six-figure salary. He said he did not want to return to the company because he was frustrated with the bureaucracy and the way the reorganization was handled. Walking away meant giving up about a few hundred thousand dollars in unvested equity.
Waters chose 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.'
That tradeoff is now common across the tech industry. Since the end of 2022, shares of Meta, Alphabet, Amazon, Apple, and Microsoft have all at least doubled, strengthening the value of vested awards for some employees. But years of layoffs have also reminded workers that stock compensation is not guaranteed. If the job disappears before vesting, the payoff can vanish with it.
Julie Zhu used that stock wealth as a cushion. The 29-year-old Apple product designer wanted to become a founder since she was 18 and said she had a 'love-hate relationship' with the company. She wanted more control over her work and wanted three to five years of runway before leaving. She said Apple stock came in handy. After nearly four years at Apple, she resigned last year to focus on Odd One In, the artist collectible company she had been building on the side.
Yousuf Imran made a similar move after about six years at Google. He set aside $350,000 for business and personal expenses before leaving in April to start an AI sales tools company. He said the potentially 'life-changing' equity packages at companies like OpenAI and Anthropic shaped his decision.
The lesson for founders is simple: compensation can be both a retention tool and a launch pad. Stock grants can create loyalty, but they can also finance the next venture when workers decide the upside belongs in their own company.
Still, the risks are real. One former Microsoft employee in her 60s said she had expected her savings and stock holdings to support retirement, but after Microsoft shares fell sharply, she began to question whether she could afford to stop working. Another former Amazon employee said salary-and-stock pay felt more predictable than bonus-heavy compensation, but even that setup depended on keeping the job. She was later laid off.
For workers, the appeal of Big Tech is not just salary. It is the combination of stock, stability, and the possibility of upside. For founders, that is why the system keeps producing new startups: every vesting schedule eventually forces a decision about whether to keep collecting checks or build something of your own.
