CTO OS
Roles is not about a JD, it's about the scope, authority level and what I expect from the people in these roles and why. What I expect from a VP of Engineering or a Principal Engineer and why. In plain English, what do they do and why. It&
CTO OS
I've spent the last 20 years building and scaling SaaS platforms. The first half was enterprise integration, learning how complex systems talk to each other at scale. The second half has been about taking that foundation into multi-tenant SaaS, leading listed and high-growth companies through international
CTO OS
I'm a scale-up CTO with 20 years of technology leadership experience, focused the last 15 years specifically on SaaS platform scale and transformation. I've held CTO roles at four NZ-headquartered scale-ups, Loyalty NZ, Plexure, Serko, and EROAD, building platforms used by hundreds of
CTO OS
Everything flows from character. It's the one thing you can't train, and it's non-negotiable. I don't compromise on hiring people with high integrity, and I expect the same standard throughout the organization. Beyond that, transparency, direct communication, the willingness to escalate
CTO OS
Resources are artefacts that have been uploaded for use within the CTO Operating System. They are input documents or data, typically in markdown format so that they can be used by both humans and agents without alteration. When in markdown, block quoted (starting with '>') sections are used
CTO OS
A Present Thread Guide is part of the CTO Operating System. It's a post that introduces a specialised type of post about a category of a concept. A Guide is something that provides context and explains it's usage.
Career
The Startup CTO exists to design, build, and operate the platform as the lead engineer, lead SRE, and lead operations person, while being deeply embedded in product decisions, establishing confidence with investors and leadership, and validating product-market fit. Preamble Throughout this essay, when I refer to "technology"
Essays
The Scale-up CTO exists to support the organization's long-term strategic goals by designing and building the capability required coming out of startup phase into iteration on iteration of scale phases sustainability, reliably and cost-effectively. Preamble Throughout this essay, when I refer to "technology"
Essays
In February 2026, I wrote that this would be the year commerce leaves the web. I meant it literally: the websites you browse to in your browser aren't where transactions happen anymore. They're moving into the AI assistant. At the time, that prediction came with significant
Essays
Here's the thing about enterprise software: it's built in layers. You've got systems that hold data. You've got interfaces that let people access that data. For decades, those interfaces were either desktop applications or websites. Both work the same way, they (typically)
Field Notes
There's a question floating around that deserves a straight answer: what are these tools actually for, and why did Anthropic build them in this order? The answer isn't about product categories. It's about what emerged from real usage. March 2023: Claude.ai Conversational interface.
Field Notes
You might have seen some of the recent noise around Claude Mythos (Preview) and something called Project Glasswing. At a glance, it sounds familiar. A company says: “We’ve built something so powerful… we can’t release it yet.” We’ve seen versions of that before. It also carries a