Chad Richardson | Waterloo Region, Ontario

Operator, builder, and a guy who likes hard problems

I'm Chad Richardson. Technology and business process have been my entire career: 11+ years as head of IT for a major North American retailer, leading enterprise technology and business process transformation, and since 2011, building the Canadian operation of a translation company from a standing start, creating workflow solutions for organizations with complex localization needs and working with AI years before it hit the headlines. Along the way I discovered the work I enjoy most: sitting down with someone, understanding what they're trying to do, and building the system and process that gets them there. No jargon. Simple.

I work with people, not for them. That's not a slogan, it's how I parent, how I coach, and how I run every client relationship. Whether you arrive with a clear vision or we uncover it together, you bring the knowledge of your business. I take the friction off your shoulders and carry it through to a solution that works. What comes out the other side is something you understand and believe in, because you helped create it, with me alongside as you grow.

Read my story

Building in public

Right now I'm deep in AI agents and workflow systems. Here's what's on the bench.

Live, runs every month end

Month-End Financial Analysis

An automated month-end review that verifies invoicing accuracy, analyzes margins against plan, and surfaces exceptions for a human to investigate. A process that used to take 1 to 2 days now takes 30 minutes, start to finish.

Live, my daily working partner

AI Clone

My daily AI working partner, built on 3 foundational layers: my voice, my personal DNA, and my business DNA. Every system I've shipped since got better because of them, and you can build your own.

Live, fully autonomous

SDR Agent

An autonomous sales research and outreach agent I built for my own business. It researches companies, writes insight-driven 1-to-1 emails, and reports back daily. Built when outside SDR services generated leads at a cost per lead that was tough to justify.

All projects

Recent writing

October 21, 2026

Pasting into AI feels unwatched, and that's the risk

Pasting a financial statement into an AI chat feels private, alone at your own computer. Here's what I learned about where that data goes, and the tools a lot of us don't think of as AI at all.

October 17, 2026

Getting to the right events, not the comfortable ones

Attending business events was the thing I kept putting aside. For 3 months now my AI working partner has lined them up, and when I pick the comfortable ones, it pushes back.

October 6, 2026

I wanted it to feel like me, not a resume.

In August I drew a mind map in my notebook with Me in the middle of the page. On October 2nd it went live as this site. Here's why I built it, and everything that sat between the page and the launch.

Read the blog

When I'm not building

Winters you'll find me on the hill, including volunteering as an adaptive ski instructor with Track3. Summers it's mountain bikes and back roads with my boys, or at the beach and on the water with my better half. The best moments in life are the ones where you're completely present, whether that's a conversation on the chairlift or hanging from a cliff face with not another thought in the world.

What could run smoother in your business?

Some of the best opportunities hide in routines you've stopped noticing, the couple of hours each week you spend on something simply because that's how it's always been done. Others are things you've never considered because they weren't practical before. Most owners I talk to aren't short on ideas, they're short on time and a clear starting point. That's a conversation I'm always glad to have.

Let's talk

Hi, I'm Chad.