The receipts, the dead ends, the Celsius — and how the machine gave the strategy and the seat their hours back.
In every sales leadership role I've ever had, I was the one trying to find systems — or hack them together — that would actually work for the team. Tools people would really use. Frankly, anything that would help us hit the number, get the team excited about what they were selling, and get them in front of clients. The tools fought back — and Salesforce led the resistance. (I hated Salesforce the most. My current org chart has been advised that fighting me is a losing game.) This was all pre-AI: I could never get it to show me what I actually needed, so I built my own consolidated spreadsheets instead. And my own forecasting docs. Path-to-goal docs. Books-of-business docs. Account plans. A whole personal operating system of documents, lovingly maintained (Andrew, Megan — if you're reading this, hi), that nobody used. Including, eventually, me. That's the cycle every sales team knows: sellers hate updating the CRM, leaders can't get answers out of it, everyone builds a workaround — and the real motion lives in none of them.
When I started Marketside, I thought I knew what the business was — what it would become, how it would scale. What I didn't plan properly for: how, with only 24 hours in a day, I was actually going to scale it. I was so fucking deep inside my clients' businesses that I had very few hours left for mine. And meanwhile, the only thing anyone wanted to talk about — at dinner parties, at conferences, in every sales group I'm part of — was AI, and how to make it work for them. Founders, sales leaders, VCs, my nail technician. You could no longer separate your business plan, your path to growth, even your system for keeping the house organized, from the machine. If you wanted to win — or at least come off as efficient and have something to say at dinner — AI had to be part of your strategy or your day-to-day. In go-to-market it was more obvious than anywhere; you could tell just from the sheer number of solutions popping up. Everyone was getting calls from a million companies with the hot new AI for prospecting, outreach, follow-up. Nobody knew how any of it was differentiated. Nobody knew how to implement it once they bought. Agents, or people? And every sales leader knows what a new tool really costs: resistance from the team below you, frustration reporting up, a real pain in the ass in both directions. And underneath all of it, half-whispered: is this thing going to replace us? (Sixteen years of watching people buy says no. It replaces the typing. It doesn't replace the trust — and the trust was always the job.)
I was asking myself the same questions, plus three of my own: how the fuck do I find time to build my own business? How do I make as much money as possible while doing as little work as possible? And where did I put literally anything? (That last one can't just be postpartum brain. I'm blaming the docs.) You were all thinking at least one of those. I'm just the one who put them on a website.
Because history repeats itself: just like the million documents, I soon had a million AI tools. I had no idea what I was doing — so I did what sixteen years of selling, managing, and trying to make sales teams more efficient had trained me to do, and tried to buy my way to understanding. Courses I never had time to take. Fourteen newsletters I have never once read. Hundreds of prompts — hundreds. GitHub (I did not know what GitHub was). More conversations with SDR bots pretending to be people than I can count. An egregious amount of money on things I had no idea how to implement. Hours in Reddit threads, nights doom-scrolling AI educator accounts — at one point I was messaging offshore CS teams trying to get them to work off my laptop. Then one day: enough. Fuck it. I drank a couple of Celsius and started attempting to build — I mean, what was the worst that could happen? A lot of trial and error. A lot of dead ends. And then something clicked. My outreach ran. My follow-up never slipped. My pipeline told the truth. And a business I didn't have hours for started running every day.
That system became the GTM Engine. I didn't build it to sell it — I built it because I needed it. Which is exactly why it works. And it didn't replace the strategy work or the fractional seats — it's what gave them room to breathe: the machine runs the operations, so the thinking and the leading finally get the hours they deserve. That's true in my business, and it's the deal in yours.