Insights
Notes from the shift to AI-native business.
Practical thinking for founders, CTOs, boards and investors working through what AI changes, what it does not and what to do next.
No recycled AI news. No breathless predictions. Just useful models, hard questions and lessons from building and leading technology.
- AI-Native CTO
- Agentic Enterprise
- Product and Engineering
- Technology Operating Partner
- Talent and Organisation
- Technology Operating PartnerPlaybook
Earned, not claimed: the six stages of venture readiness
Time spent is not progress. Evidence is. A stage model that stops a venture claiming more than it has proved.
4 October 2026·6 min read - AI-Native CTOEssay
In venture building, judgment is now the bottleneck
AI has made it cheap to research, design and build. It has made it more expensive to choose badly.
4 October 2026·5 min read - Technology Operating PartnerDecision guide
Right to play is not right to win
Being allowed into a market and being able to beat the alternatives are different questions. Most ventures answer only the first.
4 October 2026·5 min read - AI-Native CTODecision guide
Fractional CTO versus Interim CTO
Two different answers to two different problems. Choosing the wrong one costs months you probably do not have.
20 September 2026·7 min read - AI-Native CTODecision guide
When should a startup hire a fractional CTO?
The question is usually asked a quarter too late, and framed as a budget decision when it is a risk decision.
18 September 2026·7 min read - Technology Operating PartnerPlaybook
What a technology due diligence report should contain
Most reports describe a system. A useful one answers the questions the investment committee is actually asking.
16 September 2026·8 min read - Agentic EnterprisePlaybook
The AI Agent Evaluation Pyramid
Model accuracy is the least useful number you can measure. A five-layer model for testing agents before customers do it for you.
14 September 2026·8 min read - Agentic EnterprisePlaybook
Corpus Architecture: The Missing Foundation of Enterprise AI
Pointing an agent at the company document store is the most common way to build something that disappoints everyone.
12 September 2026·8 min read - Product and EngineeringEssay
Faster Code, Faster Debt
AI-assisted engineering raises the value of architecture and judgment. It does not remove the need for either.
11 September 2026·8 min read - Talent and OrganisationEssay
Most AI pilots stall for organisational reasons, not technical ones
The pilot worked. It was never going to survive contact with how the company actually makes decisions.
10 September 2026·7 min read - Talent and OrganisationEssay
Building the AI talent pipeline for agentic organisations
The work junior people learned on is the work that got automated first. That is a hiring problem now and a leadership problem in five years.
9 September 2026·7 min read - AI-Native CTOEssay
The AI-Native CTO: A New Leadership Model for the Age of Intelligence
What changes when intelligence becomes part of the technology stack and the workforce.
8 September 2026·8 min read - AI-Native CTOEssay
Agentic CTO versus AI-Native CTO
Why one is an emerging specialisation and the other is the more durable leadership category.
4 September 2026·6 min read - Agentic EnterpriseEssay
From Copilots to Coworkers: Designing the Agentic Enterprise
A practical operating model for deciding what agents should do and how humans should remain in control.
28 August 2026·9 min read