About

A working notebook.

Who

I am Darren, in Toronto, Canada. I spent most of my working life on the business side, in senior management across electronics, hospitality, technology and business services, and then at software startups, before I wrote a line of code. At a no-code platform that has since become an AI coding platform, I was the customer success and pre-sales technical lead: the person who sat with hundreds of small businesses, worked out what they actually needed built, and then made sure it worked once they had it.

One of those conversations is the reason this site exists. I asked a client what else in their business was done by hand. Fifteen supervisors, it turned out, each spending half a day a week on time cards. A small tool took that to a few minutes each, a change worth hundreds of thousands a year to the business. Nobody had asked the question before, because nobody's job was to ask it.

Today I work directly with clients on AI readiness, on what to build, and on building it. I trained in data analytics along the way, and since 2021 I have been building software myself, most of it with AI tools: CRMs, ticketing, client portals, event management, meeting booking, inventory, project management, property management, learning management systems, and a long tail of smaller tools. Most of what I know about doing that well I learned the hard way, and the rest from watching what small businesses do with software once the vendor has left the room.

That is the perspective this site is written from. Not an engineer explaining AI to business people, but someone from the business side who learned to build, and who knows what an owner is actually asking when they say "what should we do about AI".

Why this site

There is a lot written about AI at work by people who demo it, and not much by people who have to make it work inside a company and then keep it running. I wanted the second kind to exist, for the people writing the code and the people deciding what to do.

The name is the point. Ready, as in ready for AI: a business that could say the five signs out loud and answer the twelve questions without silence. CIO, as in the person whose job it is to make that true. Most small businesses do not have one, so it is nobody's job, and that is the gap this site is written into.

Everything here is from real work, anonymized where it has to be. The notes are dated and allowed to be wrong later. The playbooks are maintained. The MyVault section is the method behind all of it.

Working with me

I work with three kinds of people. Owners of businesses with ten to two hundred staff who need someone whose job it is to know what AI can and cannot do for them. Fractional CFOs, COOs and CEOs who bring me in as the AI expert their clients keep asking them to be. And the person who just became "the AI person" and wants a second pair of eyes.

It takes one of three shapes: a call before a meeting, a bounded piece of work on one topic with a written result, or an ongoing seat as the AI lead a few days a month. It starts with a conversation, not a proposal. If the honest answer is that you do not need me yet, I will say so and point you at the pages here that will get you further.

Two things you can count on. Everything I write for you is meant to be forwarded, in your language, not mine. And I keep the number of clients small enough that each one gets my attention, which is the only way this kind of work is worth paying for.

If that sounds like what you need, say hello below.

Say hello

Tell me which of the three people you are and what is going on. A first conversation is a conversation, not a proposal. I read every one and reply to most within a couple of days.

Prefer LinkedIn? Connect and message me there. Email works too: darren@readycio.com. I am in the Toronto area and work with people wherever they are.