ClickUp Cut 22% of Staff. Here's Why "100x Employees" Is the Real Story

19 Jun 2026 · 1 min

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1:09

In this commentary, the host (addressing a colleague named Neil) examines the recent 22% staff reduction at ClickUp and the accompanying narrative of hiring "100x employees," comparing it to a similar layoff at Cloudflare where the CEOs posted lengthy statements on X that garnered millions of views. The speaker emphasizes a business‑operator perspective rather than a surface‑level news reaction, highlighting that ClickUp operates in a software category—project‑management tools like Asana and Atlassian’s Jira—that is being heavily disrupted by AI, making it one of the hardest‑hit sectors. He references Naval’s idea of "10x/100x engineers" to argue that the traditional notion of a 10x engineer is outdated, and that companies are now seeking a new class of hyper‑productive talent to justify restructuring. The overall tone is analytical and conversational, with a critical view of the hype around "100x employees" and concern about AI’s impact on the industry.

Chapters

Neil, obviously you've seen this, that ClickUp, you know, they cut 22% of staff and they're talking about getting 100x employees. And then Cloudflare did this thing where they did a layoff and then each of their CEOs wrote a really long post on X and it got millions and millions of views. And then, you know, you've heard people that have different opinions on this, right? So let me pull this up real quick and then we can react to this because I want to talk about this from a business operator angle versus just reacting like someone from the news. So Jason Lim can put this up here. So Zeb from ClickUp, I just want— he's the CEO founder of ClickUp. And so looks— this post has 9 million views. Oh my God. Wow. Okay. So I think folks are partially missing the story here. ClickUp is in the category perhaps most devastated by AI. So we kind of talked about this last week, but I want to react to it more. So Monday, Asana, et cetera, are further down than anyone else. Atlassian Jira was too until the last quarter, literally the worst category of software in the AI age. What I want to talk about here is this whole idea of focusing on 100x employees. Because if he needs to, like ClickUp or Cloudflare, they need a cut and they're talking about making way for 100x employees. Naval has talked about this concept of you're not even like a 10x engineer anymore. You're not even a 100x engineer.