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Jason Lemkin makes a blunt case that quitting your tech job in 2026 is far riskier than it was in 2021, and most people underestimate how much the math has changed. He shares that SaaStr itself went from 20-plus employees to three humans and 20-plus AI agents, flipping revenue from negative 19% to positive 47%. The uncomfortable part: when someone quits voluntarily now, many CEOs are quietly relieved because it saves them a hard conversation and frees headcount for AI tooling. The 2021 playbook of quitting Friday with three offers by Wednesday is gone. Lemkin’s advice is to use a boring but stable role as cover to build skills for the next chapter rather than leap into a hiring market that has structurally contracted.
