Shadow AI and the Wild West: Why your pilots are failing for the wrong reasons
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Plus: How Jay and the human team maintain a 4.9 Trustpilot score
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From the aibl team
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Why does AI adoption often stall in the middle of the organisation? Because while budgets get approved, pilots get launched, and leadership makes the right noises, nobody has worked out what the job actually looks like on the other side.
Recently we spoke about this to Tim Flagg. He co-founded UKAI, the country’s trade association for AI businesses, after years building AI products himself and getting frustrated with an industry short on accountability. Tim sits across a membership base at every stage of AI adoption, so he sees how mid-market firms are actually doing this: most haven’t got past experimenting.
Now that agents are part of the picture, the people being asked to redesign how work gets done get very little support and often get unclear expectations from every direction. Most AI strategies skip over them. Tim also has a good take on what buyers get wrong when purchasing AI, and draws a parallel to ESG that I hadn’t heard before. The article’s below.
We’re asking a closely related question at workforceLIVE on 6th May, a Chatham House Rule working session in London for 50 senior HR, People, Talent and Capability leaders, with Dr Laura Weis of WPP guiding the discussion. Part of our new 2026 aibl Leadership Series, it’s free to attend, either by invitation or you can apply here.
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How UKAI’s founder sees the mid-market AI gap
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This article is drawn from a recent conversation with Tim Flagg, co-founder and CEO of UKAI.
Tim Flagg spent years building AI-driven products at companies like EntityX, Greater Than and Intelliquence. He witnessed how quickly this new industry was accelerating, but he also saw the risks and was concerned that the industry was becoming a ‘Wild West’.
So he co-founded UKAI, the country’s only trade association for AI businesses, bringing together companies that wanted to build a more responsible industry.
The organisation now works closely with the government (Tim was speaking with AI minister Kanishka Narayan just days before our conversation and UKAI regularly runs workshops with numerous departments) and across a membership base that gives him a particular view of how mid-market firms are actually adopting AI.
Some firms are running structured pilots. But from what Tim sees across the market, a large proportion are not. In their place: shadow AI – people using their own tools and platforms, outside any structure the organisation has set.
When people are on different pages, using different systems at different levels of maturity, pilots fail for structural reasons and leadership draws the wrong conclusion. “People sort of will say, well, AI failed,” Tim puts it. “Without really thinking about which bit of AI it was that failed and whether it was a fair test.”
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Watch the full video interview:
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How Just Move In split the work between AI and the team
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Recently we spoke to Ross Nichols, co-founder of Just Move In, about why they rebuilt their 10-year-old platform around AI. This week we’re looking at how their AI, Jay, and the human team work together day to day.
Before Jay, a move specialist would spend 20 to 30 minutes on a single call. Every customer started from scratch. The specialist walked them through the full process – what services they needed, when to switch, what options were available. But that approach couldn’t scale – to offer services beyond energy, broadband and insurance, they’d have needed a much larger team.
Jay launched in mid-December. Energy is the first service running through the AI. Insurance and broadband follow by end of Q1, each added individually because every supplier process has different nuance.
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Product spotlight of the week
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This week we’ve been tracking Tray.ai, an integration platform that’s picked up momentum with mid-market teams tired of stitching together SaaS tools with spreadsheets and manual workarounds. Enterprise iPaaS like MuleSoft typically means six-month implementations and dedicated dev teams. Tray takes a low-code approach that lets business technologists build and manage workflows themselves.
The platform connects to 600+ apps including Salesforce, HubSpot, NetSuite, Slack and Jira. They recently added Merlin, a natural language agent builder for creating AI-driven automations without writing code. They’ve also launched a SQL Transformer for processing large datasets in-flight, handy if you’re trying to get AI projects past the pilot stage without spinning up separate data infrastructure.
There’s a 14-day free trial with full platform access, no credit card required, and pre-built templates to test real workflows before committing. For mid-market ops and IT leads who need integration that scales without an enterprise contract, it’s worth a look.
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