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Present Thread is where I explore what I’m seeing now, and what I think is coming next. Of all the threads in motion, which one is the present thread?

CTO Operating System

The CTO Operating System is a structured collection of resources, tools, practices, agents and other artefacts that describe how I actually work. It's a site which is like the candid non-verbose intro, like my own guidebook documented on being a scale-up CTO in publicly listed SaaS technologies companies built on experiences on working with some of the worlds Tier 1 brands.

The CTO Operating System has a beginning but no end. It's an ever evolving system with what I'm seeing and using in my role as the CTO and like technology it changes over time. It's a system for understanding myself and enabling AI agents to prepare me for conversations and decisions and sharing that with others.

Why it exists

Two reasons: First, clarity. Documenting how I operate forces me to be intentional about decisions, values, and tradeoffs. Second, utility. When I'm preparing for conversations with CEOs, boards, or interesting opportunities, agents need context — not just my job titles, but how I think, what matters to me, what I'm optimized for, and what I've been exposed to. This system provides that.

Resources

Downloadable artefacts, typically markdown files designed for both AI processing and human adaptation, sometimes as word documents when specifically targeted for human use. All Resources are found on the Resources page.

Guides

A detailed explanation of a concept / post type, with the CTO Operating System as the core lens:

  • Perspectives - A guide to the foundational explanations of how I operate, thinks and approach technology leadership, structured as readable articles with links to detailed markdown Resources for AI and human use
  • Resources - A guide to the downloadable artefacts, typically markdown files designed for both AI processing and human adaptation, sometimes as word documents when specifically targeted for human use
  • Roles - A guide to the what certain roles do in technology
  • Agents - A guide to the AI Agents I have built to help in performing my role.

Perspectives

How I operate, think and approach technology leadership. These perspective provide the foundational work for the CTO Operating System and they also come with Resources in markdown so they can be fed into all sorts of agents, they are my documented context:

    • Culture - My perspective on how I work, what I value and how I show up as a leader
    • Situation - My perspective on my own current professional situation, what I'm looking for, and how I'm positioned in the market
    • Work History - My perspective on my professional career timeline, roles held, and key accomplishments across scale-up and enterprise environments
    • Philosophy - My perspective on how I think
    • Technologies - My perspective on the technologies I've used and the technology companies I've built partnerships with over the years, support, engineer, CTO and researcher
    • Challenges - My perspective on how I learn. Note this is a synthetic post and the challenges.md file on Resources contains synthetic data

Agents

AI agents I have built to help in performing my role. Not overhype and overused, just simple helpful agents that can do things repeatably in a fraction of the time I could:

Opportunities For Me Agents - Recruitment Outwards, knowing what you know about me:

  • Role Evaluation Agent - What's the score of me to this role, this role to me and why?
  • Due Diligence Agent - Whilst in Due Diligence, tell me as much as you can specifically about the company, products and people we are looking to acquire.
  • Conversation Preparation Agent - I know about this company, but prepare me well for up an coming conversations. What is the latest news, what should I know, what should I go deep on, what will they ask me?

Public Speaking Agents - I'm about to speak publicly on a topic to an audience, I know the subject matter but I want to hone it and provide the best possible experience for the audience:

  • Keynote Preparation Agent - Help me prepare for a keynote speech
  • Panel Preparation Agent - Help me prepare for a panel discussion or a fireside chat
  • Panel Moderation Agent - Help me prepare for a panel discussion where I am the moderator

Roles

My take on what certain roles do in technology:

  • The Startup CTO - The startup CTO is the lead engineer. They're writing code every day, running operations, managing incidents at 2 AM, and embedded in product decisions
  • The Scale-up CTO - The scale-up CTO has stepped out of hands-on execution. They're designing the technical organization for international expansion, building multi-region architecture and compliance frameworks, scaling operations across time zones and markets, and translating between technical strategy and the growth imperatives that boards and investors are pushing for
  • The VP of Engineering - My goto guy / gal. Everything engineering. In the heat of things. Leader, optimiser, awesome person who runs the all important machine, can give me the real feedback and helps me make good calls. Think my GP.
  • The Principal Engineer - Probably the most important technology people in the entire organisation. Our on the ground best in breed most senior software engineers, everyday balancing between their excellence of individual contribution and leadership / scale contributions