Most AI service failures are not model failures. They are organisational ones.
Writing
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Context engineering isn't enough
7 minYou can hand a model a flawless context window and still get the wrong answer, because nobody in the company ever agreed what the right one was.
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Never don't invest in the content base
6 minRetrieval cannot find what was never written down. The least glamorous function in the building quietly became the highest-leverage one.
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What AI service actually feels like from the other side
8 minCustomers are not evaluating your architecture. They are asking one question, over and over: does this thing have any power to help me?
About
I've spent more than ten years working on customer experience from the technology and strategy side — the part where a service promise either survives contact with real systems, real content and real people, or quietly doesn't.
Most of that time has been spent in the gap between what a company says it will do for customers and what its infrastructure will actually let it do. I've worked on the platforms, the routing, the knowledge, the measurement, and the operating models that sit underneath support at scale. The interesting problems have almost never been the ones the org chart said they were.
I currently lead customer AI at Xero, a team I formed to work out how large language models change service delivery in practice rather than in demo. That work has been the clearest confirmation of something I'd half-believed for years: the constraint on great service was rarely effort or intent. It was cost, latency and the sheer impossibility of knowing every customer's context at the moment they needed you. Those constraints have moved. Very few companies have caught up to what that means.
I write here mostly to think out loud about that gap. Views are my own, examples are generalised, and nothing here is a statement on behalf of my employer.
Where I spend my attention
- Designing service operations around what AI is genuinely good at, rather than bolting it onto a process built for humans reading scripts.
- Knowledge and content systems — the substrate everything else in AI service depends on.
- Measurement that survives scrutiny: resolution and trust, not deflection.
- The organisational side of AI delivery — decision rights, ownership, and who is accountable when an agent gets it wrong.
Contact
I'm glad to talk with people building in customer experience and applied AI — comparing notes, arguing about measurement, or working through a problem you're stuck on.
Reach me at hello@bengilmore.online.