Cloudflare CEO on how he chooses which employees to replace with AI

oradwan 56 points 28 comments May 20, 2026
www.wsj.com · View on Hacker News

Discussion Highlights (15 comments)

jauntywundrkind

I'd really love to read this article; this feels like it's totally under-explored, not discussed. Paywalled.

Cider9986

Unpaywalled https://nonogra.ph/how-i-choose-which-cloudflare-employees-t...

pesus

> Two weeks ago I laid off more than 20% of my workforce. I didn’t do it because Cloudflare is struggling. We posted record revenue growth, have strong free cash flow and are adding an unprecedented number of customers around the world. Huh, I wonder why people hate AI so much? > AI isn’t the harbinger of bleak youth unemployment—it is quite the opposite. This makes no sense and directly contradicts everything else said before. How is gloating about how you're laying people off despite making more money than ever supposed to increase employment? Do they honestly believe everyone is gullible enough to believe blatant lies like this?

fny

> AI isn’t coming for builders or sellers, but it is coming for measurers. Tireless, independent, efficient and available, AI systems can now measure an organization with a level of objective detail and precision that was previously impossible even for the best employees. Honestly not the apocalyptic scenario I had on my bingo card.

lazyant

> The interns we hired are extremely qualified and AI-native. wtf is "AI-native" ? couldn't he say "familiar with AI tooling?"

SaucyWrong

I suspect these reasons are just more AI-washing of a mass layoffs indicative of pandemic-era business mismanagement, but supposing they aren’t… Watch Cloudflare closely and hold Matthew Prince accountable to all of these statements. If LLMs enhance their builders while simultaneously making their measurers redundant, investors should expect record business growth, drastically fewer outages, and few if any security and compliance fails.

peterbecich

The distinct categories of building, selling and measuring seem fallacious

ewy1

potentially ruining thousands of lives over some shit you read in a seventy year old book is a very normal thing to do

throwway120385

Yeah, measurers. You know, the people who help you verify claims such as "the LLM is measuring your organization accurately."

gamblor956

Next year's headlines: Cloudfare fires CEO after year of AI vibe-coding related outages cause hundreds of millions in losses.

nullbio

Everyone who gets fired should be teaming up to start a competing product.

another_twist

What was the compostion of folks let go by Cloudflare ? How many working in profitable lines ? How many in loss leaders ? How many engineers ? How many supporting business functions ?

rdtsc

The LLMs will now measure their own performance and conclude it’s stellar and the company should buy more LLMs tokens

gmerc

Loer-Value humans as the Standard Charter CEO calls it https://www.channelnewsasia.com/business/standard-chartered-...

brumar

So HR and middle management, legal is ... measuring? They want to focus on builders and sellers but will support them like robots. A great recipe for disaster. Legal is measuring too? I can't wrap my head around the reasoning process here. Unless cloudflare is going to be a teal enterprise (from the reinventing organisations book), I don't see how it makes sense.

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