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Watching the AI inside your tools

Good morning. Two things are happening to business software at once, and today they turned up side by side. The AI now built into everyday tools is doing more on its own, and the way companies decide what to buy has grown harder to read — which puts a plainer question in front of every buyer: what is your software actually doing, and who can see it.

Most of the items worth your attention today sit on one side or the other of that question. Some are about the AI inside the tool. Some are about the market the tool is sold into. Both end up at the same place: you need to be able to inspect what you are running and trust that the company behind it will still be there next year.

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What we're tracking

  • Seeing what the AI does inside your tools When a feature stops being something a person clicks and becomes something a model does on their behalf, a gap opens in your records. The old assumption — that every action in a system was taken by a named human — no longer holds, because now a person and a model act together. That makes an audit trail harder to read and more important to have.
  • Buying software in a market that keeps moving TechCrunch reported research arguing that a startup's recurring revenue is less secure than it has been, and pointed at the cause: new buying behaviour in the AI era [2]. For a buyer, this is not gossip about vendors. It is a warning about the ground under the tools you depend on.
  • Running more than one AI agent at once GitHub published a guide for beginners on running several agents at the same time in its Copilot app, framing it as the moment the idea stops feeling frightening and starts feeling capable [3]. An agent, in this sense, is software that carries out a multi-step task on its own rather than waiting for a click at each step. Running several in parallel means more work happening at once, with less of your attention on each thread.
  • A stack of tools that works together Xero announced the winners of its 2026 App Awards, and opened with a line that is worth sitting with: behind every thriving small business is a stack of tools cutting through the noise [4]. The word that matters there is stack. Almost no business runs on one application. It runs on several, and the value is in how well they pass information between each other.
  • How a large vendor's numbers read SaaStr looked at Salesforce at roughly $45 billion in recurring revenue, noting that it reported its quarter on 26 August and the stock rose 23 per cent [5]. A small business is not Salesforce, but reading a large vendor's results is still a skill worth having, because the tools you buy are often sold by public companies whose numbers are in the open.

From the blog

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