Guides & Resources
Practical frameworks and thinking for technology leaders navigating platform decisions, transformation programmes, and investment due diligence. Organised by the questions that come up most often.
Whether AI-built work is right, whether it survives production, and how to verify it rather than hope.
Why agent stacks fail at verification rather than capability, and how to build your first golden-set eval in an afternoon — with the real tickets, the real bake-off, and the rules that keep a suite honest.
AI made building almost free. Surviving production is as hard as it ever was — and that gap is the whole game.
When to replatform, how to manage the transition, and what usually goes wrong.
A practical checklist for leadership teams assessing whether their organisation is ready for a major technology transformation , covering strategy, team, data, and governance.
A structured framework for evaluating and selecting technology platforms , covering business fit, integration architecture, total cost of ownership, and vendor evaluation.
After 18 years and dozens of transformation programmes, these are the patterns I see repeatedly. Most failures are not technical. They are organisational.
Most replatforming decisions are made too early, too late, or for the wrong reasons. Here is how to tell when the pain is real and the business case stacks up.
Platform selection is one of the highest-stakes technology decisions a retail business makes. Here's a framework for making it well.
Where AI delivers real operational value in retail, and where it is still mostly hype.
Separating genuine operational value from vendor hype. A practical guide to where AI delivers measurable results in retail, and where it is still mostly theatre.
After advising several retailers on AI adoption, here's what I've seen actually deliver results , and what tends to be expensive distraction.
The data foundations enterprise AI actually needs before any of it works.
Customer data strategy, CRM capability, and whether you actually need a CDP.
CRM implementations in retail fail at an alarming rate. This article diagnoses the common failure patterns and provides a practical remediation framework, including when to fix what you have and when to start again.
The CDP market is crowded and confusing. Before you sign a six-figure contract, here is how to work out whether a customer data platform will solve your actual problem.
Platform architecture, integration strategy, and the headless vs monolith decision.
RFPs, beauty parades, and feature comparisons waste time and lead to poor decisions. Here is a structured, practical approach to evaluating technology vendors that actually works.
Integrations are where most retail technology programmes fail. A practical guide to architecture patterns, middleware decisions, vendor management, and the human side of keeping systems connected.
Cut through the hype. A structured framework for deciding whether headless commerce, monolithic platforms, or a composable middle ground is the right architecture for your retail business.
Operating models, fractional CTO engagement, and building technology capability.
Most companies treat AI as a feature to bolt onto something they already have. I treated it as the product itself — shipped a complete, multi-tenant pricing intelligence SaaS in two weeks, then iterated. Here's the discipline that makes that pace real, not theatre.
Most retail businesses treat technology as a cost centre. This article makes the case for embedding technology as a product function, and provides a practical blueprint for what a modern retail tech operating model looks like.
Most people use AI as a smarter search engine. I built an AI agent called Sally that operates as infrastructure — managing projects, surfacing priorities, and scaffolding work before the first coffee. Here's what happens when you stop using AI and start building with it.
The fractional CTO model is growing in popularity, but the role is often misunderstood. Here's what it actually involves, when it works, and when it doesn't.
Technology assessment for PE, VC, and M&A. Pre and post acquisition playbooks.
Portfolio technology standardisation promises cost savings and operational leverage. This article separates the genuine opportunities from the common pitfalls and provides a phased approach to getting it right.
You have closed the deal. Now what? A practical guide to the technology decisions that matter most in the first 100 days after acquiring a retail or commerce business.
Most tech due diligence reports tell investors what the stack looks like. They rarely tell you whether it will support the investment thesis. Here is what to actually look for.
If any of these topics are relevant to what you are navigating right now, I am happy to have a conversation about your specific situation.