MW Okta CEO Todd McKinnon has words of caution for people jumping ship to work at AI startups
By Aditi Shrikant and Emily Bary
Why it's not always smart to jump ship for a flashy job offer
Okta CEO Todd McKinnon said his career journey can hold lessons for workers in the AI era.
Todd McKinnon might never have become CEO of $16 billion software company Okta if not for an uncool move he made early in his career - and one that goes against the conventional wisdom.
As his coworkers bailed for "sexy" jobs at internet startups during the height of the dot-com boom, McKinnon made the seemingly boring decision to stick things out at PeopleSoft, a maker of human-resources software.
"It turned out to be the best thing ever," he told MarketWatch. Not only was he promoted and given meaningful projects, but "when all the dot-com companies started going out of business, it was good to be at a company that had real customers, real revenue."
McKinnon didn't stay at his job out of inertia. Rather, he made the decision because he was assigned to fun and challenging assignments. One project was related to an identity-management platform and proved foundational when he went on to cofound Okta $(OKTA)$ in 2009.
He thinks today's coders should keep the lesson in mind as they weigh the allure of jobs at AI startups. McKinnon saw dot-com companies with "a lot of high funding and a lot of fanfare" that never amounted to anything.
Now, "there's a good analogy here with AI," McKinnon added. It's a cautionary piece of advice for people who are considering giving up their job for a shot at the unknown, particularly with thousands of AI startups operating globally.
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When to stay put
For McKinnon, a steady stream of challenging opportunities made him realize there was ample room to grow at PeopleSoft, where he ended up staying for eight years.
This advice might seem counterintuitive because historically, job hopping has paid off for workers: from April 2021 to March 2022, employees who switched companies saw a 9.7% year-over-year increase in real wages, which is your pay adjusted for inflation, according to data from Pew Research Center. Workers who stayed put actually experienced a 1.7% loss.
More recently, the strategy of switching companies for a pay bump hasn't been as reliable. From February to July of this year, job stayers actually saw more wage growth than job seekers, according to data from the Federal Reserve Bank of Atlanta. But in August and September, job hoppers once again had more significant pay gains.
While gender, race and age all affect which opportunities are available to you in the workplace, there is a rule-of-thumb that works for most people wanting to move up professionally, says Meggie Palmer, founder of career development company PepHerTalk. "Shifting roles every two to four years can really contribute to a substantial salary increase."
There is a "fine line" between applying to too many jobs and looking complacent, she says. Undertaking a new challenge every few years can show employers you're ambitious, but not flighty.
"You don't want to be job hunting every year, but if you stay at a company for 8 to 15 years, that can hinder success too," she says.
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Return on investment
Even if you don't change companies, you should be pursuing challenging projects, as McKinnon did, to show your managers that you are learning, growing and adding value to the company.
Pursuing a promotion should be an ongoing discussion, not a one-time ask. Record your "wins," research the market value of your job title and responsibilities, and check in about what you could be doing better at least once a quarter.
"How have you reduced costs?" Palmer says. "How have you improved culture? What is the meat on the bone for the proof that you are contributing on a real substantial level?"
The most successful workers are ones who make it known that they want a promotion, and are consistently building the case for that raise.
For McKinnon it paid off to stay rather than move to a startup that might or might not pay off. "It was much more damaging to go there and waste a few years of your career versus sticking at a real company and learning and growing and building," he said.
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-Aditi Shrikant -Emily Bary
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December 22, 2025 08:00 ET (13:00 GMT)
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