Issue #724, 9th October 2026

Budding vs. Splitting: A Better Model for Growing an Engineering Org
5 minutes read.

Worth reading for Daniel Pupius's end-game: the core team exists to find the shape of the work, and it should stop being necessary once that shape is known. You end up with roughly the org chart you would have drawn on day one, but the boundaries emerged from the work instead of being guessed up front: "The end-game for this process isn’t based on headcount; it’s more of a condition or a state. The core team exists to find the shape of the work, such that it stops being necessary once the shape is known: which typically aligns with PMF being found. At this point, the surface area is mapped, and a team is sitting on each part of it." Which boundaries in your org were chosen when you knew the least?

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Building a Company in 2027
1 minutes read.

My humble effort to help you start the weekend with a smile.

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GTM Is Getting Compressed: The Way We Buy and Sell Software Is Changing Faster Than the Playbooks.
4 minutes read.

Patrick Thompson argues we should all focus more on the agentic experience on our storefront, as buyers now send agents to analyze reviews, draft the RFP, and compare vendors before a human talks to you. Soon agents will sign up and trial your product too. Are you optimizing your storefront and onboarding (docs, pricing page, API) for agents as much as for humans? How easy is it for agents to reach the first "aha!" moment and report it back to their team?

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Context Is Now the Product: Product Leadership When Software Can Build Itself (Video)
17 minutes read.

Karri Saarinen (CEO of Linear) names the real risk of automating product work: "the more we automate things with AI, and the more we automate or tell teams to use AI, the more of a gap is created between execution and learning." -- Struggling with what to build was always how we learned the customer's problem. If your team now skips the struggle, what exactly are they learning? Worth watching.

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Will Agents Have Network Effects?
9 minutes read.

Great insight by Andrew Chen on agentic viral loops: an agent has every incentive to host the mini-app or shareable board itself instead of creating a Google Sheet, because that spreads the agent and not the other product. I like the idea of reading your own roadmap through this lens. Every artifact your AI feature creates is either a growth loop for you or free distribution for someone else.

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Your Reader Has a Context Window Too
5 minutes read.

Whatever your agents write (PR summaries, incident reports, status updates), design for how fast a human finds the action, not for how short the text is. Great lesson from Remus Lazar on why long AI-written docs get ignored: "So it was never the volume. It was the time to first useful token, how long he had to read before he found the thing he actually had to act on. [...] Length is a bad proxy for cost. It is just the only one that is easy to measure, which is why we all reach for it."

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Maybe Making Is About Mattering
3 minutes read.

"It's never been about the technology. It's always been about the people." Short and worth reading as a reminder when your team debates which model or framework to adopt this quarter. What would change in your roadmap if every item had to name the person whose life it makes better?

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ETOOMANYTHINGS? Run Fewer Agents
4 minutes read.

Josh Bleecher Snyder's on-screen recording and audio recording idea made me think about the products we build. Do we want to create deeper engagement by fully emerging with how humans operate and how agents respond? "...concurrency is really rough on humans. It’s stressful. It trashes flow state and thrashes our mental page caches. Task management isn't a solution; it's a band-aid. [...] How can we restore human agency and optimize for human I/O, rather than making the human adapt to the agent?"

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@readswithravi: “Stop being patient and start asking yourself: How can I accomplish my 10 year plan in 6 months? You will probably fail, but you'll be far ahead of the person who simply accepted it would take 10 years.”

@BrendanFoody: Two things matter most when hiring executives or promoting leaders internally: 1. Can they hire exceptional people? 2. Can they solve hard problems? External executives are usually experienced at building teams, but often lack the context and content depth to solve the hardest problems themselves. Internal leaders usually get promoted because they’re exceptional problem solvers. The question is whether they can become exceptional at hiring. The best leaders can do both.