HeyJaredDrea Says Product Things
Occasional rants about product things. Let's demystify things together!
- Indexed issues, last 90 days
- 6
- Latest publication
- Sep 29, 2026
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- Aug 2, 2026
Latest issues
Claude 5.5 is brilliant, confusing, and very hungry (opens the original)
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Anthropic just shipped two new models as part of their 5.5 series. The launch threads on Reddit and Hacker News moved quickly past benchmark scores to more practical questions about which model to pick, why security work keeps getting blocked, and when usage limits reset (that last one by far the loudest). I read both threads and the first independent benchmarks so you don’t have to. Put your nerd hats on!TL;DROpus 5.5 takes the top spot on the Artificial Analysis Intelligence Index at 58, beats
What is AI saying about your company? Here’s how to find out. (opens the original)
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Welcome to another session of I did the hard work so you don’t have to: AEO edition.TL;DR:You can rewrite a positioning statement in an afternoon, but you cannot rewrite what the internet, and by extension what AI, already believes about your company at the same speed. Those are two different projects on two different timelines, and most GTM teams only budget for the first one.How AI forms an opinion of a companyAn AI system doesn’t have one settled answer to what your company does. It’s working
How to structure an AI GTM team in 2027 (opens the original)
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I’ve built GTM teams from scratch more than once, and the same shape keeps showing up. The org chart everyone inherited needs to be flipped upside down because of what AI can do now.GTM Organisation is impactful to the cost and way a business is run. There’s no room to get it wrong. GTM teams are leaning harder into the strategic layer of the org and pulling back on execution headcount. The data backs it up. <a href="https://www.gartner.com/en/newsroom/press-releases/2026-05-11-gartner-2026-cmo-
Why all AI content sounds exactly the same (and how to fix it) (opens the original)
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Ever notice that AI copy has a smell? It’s the distinct smell of confident bullsh*t.All AI copy contains the same rhythm, structure, landing, and shitty dismount no matter who prompted it (I was once a gymnast, stay with me here.) AI slop is everywhere, and the reason is more than just lack of copywriting skills. TL;DRAs previously explained, LLMs don’t pick words freely. They sample from a probability distribution over what to say next, the first during pre-training, and the second during align
Putting Claude’s watermarking to the test (opens the original)
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Anthropic has just started marking Claude’s output and has signed the EU AI Act’s Article 50(2) Code of Practice on Transparency of AI-Generated Content, confirming it started embedding machine-readable watermarks in text from new Claude models on August 2, 2026.That announcement is a good excuse to actually explain how this category of technology works, because most people assume watermarking means hidden code slipped into the content, a few invisible characters or sneaky whitespace tucked in l
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