Saturday morning. Doug took Max to a tournament, Zoe is still asleep. I have the kitchen table, my laptop, and the question Terri asked me two days ago that I still can’t answer.
Who signs the check?
I have LinkedIn open. I’m looking at VP of Customer Success profiles at mid-size SaaS companies, trying to figure out who would pick up the phone if I called and said “you’re about to lose three of your biggest accounts and I can tell you exactly why.”
The VP of CS knows the problem exists. They’ve watched the same retention numbers I have. They know the last 60 days before renewal are where deals go to die. But they don’t have discretionary budget for outside help. Their money goes to headcount and tools, not a person like me showing up for eight weeks.
The VP of Sales has budget. VPs of Sales always have budget. But renewals aren’t interesting to them. New logos are the thing. Nobody gets a standing ovation at the annual kickoff for saving a renewal that was about to churn.
The CFO cares about the money. A $400,000 account not renewing is a $400,000 problem. But the CFO doesn’t know what a renewal process looks like and isn’t the person I’d be working with day to day.
So I’ve been sitting here for an hour, reading job descriptions and mapping the org chart of a hypothetical company, and I’m starting to realize something. This is what I do. When I don’t know what to do next, I research. I open tabs. I read things written by people who figured it out before me and I take careful notes and I feel productive. I am being productive. But I’m also doing the thing I’m good at instead of the thing I’m scared of.
I’m good at research. I’m scared of selling.
Around 10:30 I closed LinkedIn and opened a blank document. Three columns: Title, Budget Authority, Cares About Renewals. The person who checks all three boxes might not exist as a single human being. Maybe the sale is two conversations. Maybe three. I don’t know. I have never sold anything in my life that wasn’t someone else’s product with someone else’s brand on the invoice.
That sentence is the one that stopped me.
Because it’s not true.
I have spent 24 years selling. Renewals, upsells, expansions, platform migrations, pricing changes nobody wanted. I have looked a CTO in the eye and explained why a 14% price increase was actually good news. I am a person who sells things. But I have never sold myself. I have never been the product on the invoice. And I think the distance between those two experiences is most of the distance I still need to cover.
Doug got home around noon. Max’s team won. He was in that good Saturday mood. He saw the laptop open, the notes spread out, the three-column document on screen.
“Working on a Saturday?” he said.
“Just some research,” I said.
He didn’t ask what kind. He went to make a sandwich. I closed the laptop.
I could have told him right there. He was relaxed, the kids weren’t in the room, there was nothing pulling at the afternoon. I could have said: “Actually, I need to talk to you about something.” I had the sentence ready. I’ve had it ready for weeks.
I didn’t say it.
Part of me knows why. The longer I wait, the bigger the silence becomes. It’s not just “I’m thinking about leaving” anymore. It’s “I’ve been thinking about leaving for months and I didn’t tell you and I started writing about it on the internet and strangers know more about my plans than you do.” That’s a different conversation. A harder one. Every day I don’t have it, the conversation gets worse.
I’m going to tell him. I need to tell him. But I keep thinking I should figure out the business part first, so I have something concrete to explain. Which, now that I type it, sounds a lot like the same problem I was working on this morning.
I still don’t know who signs the check. I still haven’t told Doug. And I’m starting to wonder if the reason I can’t do either one is simpler than I want it to be: both require me to say out loud, to a real person, “this is what I’m doing.”
Not “thinking about.” Doing.