CTO OS

Role: VP Engineering

The leader of leaders.

The person who gives me day to day confidence, who builds, grows and optimises our engineering function, and when I take time off, seamlessly steps into day to day CTO operations and shields me.

When I want to vent has an ear, and when who needs to vent can do so.

If I'm in the World Cup final and we're 2-0 down, is planning with me and with all honestly on how that's gonna end 2-3.

This is a really interesting role. It's because it's such a senior role that I need them to own their ship. People, process, software, execution. They need space and autonomy to own engineering, make decisions, inform me. I've been in there, in that engine but I need them to take reigns and feel they own, outcomes and accountability.

Perspectives: Challenges

Note: This essay discusses my approach to challenges using synthetic examples. Real detailed STAR examples are in a private markdown resource shared selectively under NDA. I learn more from difficult situations than from smooth operations. The decisions that teach me most are the ones where multiple stakeholders have competing interests,

Perspective: Technologies

My relationship with technology spans four distinct phases, each informing how I think and what I can do today. As a Technical Support Specialist at Microsoft UK I learned how technology actually fails. I supported Visual Studio, SQL Server, and COM at the product level, debugging customer issues under pressure

Perspective: Philosophy

Philosophy, how I think. Character and Patina I believe people are shaped by pressure, not despite it. Character isn't built in comfort, it's built in difficulty, failure, and the choice to stay and learn rather than retreat. When I look for people to work with, I&

Resources

Resources are downloadable supporting artefacts, sometimes markdown files designed for both AI processing and human adaptation, sometimes as word documents when specifically targeted for human use. Perspective Markdown Files These are markdown files that describe how I show up, my history, my experiences etc. I use them as inputs into

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Perspectives: Challenges

Perspective: Technologies

Perspective: Philosophy

Resources