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Dated 2023, written in 2026. Reconstructed from notes and posts from that period rather than published at the time. The thinking is what I had then; the sentences are new.

The first good month

Vigilance is working. Plus merchants are signing up and the math isn't a stretch. I've been here before and I know what it does to your judgment.

3 min readvigilance · shopify · growth

Vigilance is working. Shopify Plus merchants started signing up in January and haven't stopped. For a brand doing real volume, the value of blocking unauthorized code injection is not a pitch — it's arithmetic, and the arithmetic is visible on their own dashboard within a week.

This is the fourth time I've been in the early-traction phase of a company, and I've learned that it's the period where I make my worst decisions. So this is a note to myself, written while it's happening, about what the feeling is doing to me.

What early traction does to your judgment

You start believing your thesis was right. It might have been. It's also possible you found one segment that has this problem acutely and are about to generalize from it. Every company I've built has had a moment where a specific customer type worked and I concluded the market worked.

You stop discounting the risks you'd priced in. I raised this round having said out loud that this product depends on a specific behavior of a specific platform. That was true in August and it's exactly as true now. But traction is an anesthetic — the risk hasn't changed and my felt sense of the risk has dropped considerably, purely because revenue arrived. That's not information. That's mood.

You want to hire. Everything is working, there's more demand than capacity, and the obvious move is to add people. I've written before about under-hiring being my defect. The overcorrection is hiring against a growth rate you've had for one quarter.

You stop selling and start managing. The activities that produced the traction get displaced by the activities that traction generates. Support, onboarding, the operational load of having customers. I've watched growth stall at exactly this transition twice.

What I'm trying to hold onto

The risk I named at the raise hasn't gone anywhere. Vigilance operates inside checkout. Checkout is the part of Shopify with the most active roadmap and the strongest platform opinions. I said in August that I'd rather be the person who flagged it, and the flag is still up.

Concretely, what that means right now:

Not hiring ahead of the revenue. However good this quarter looks.

Reading the platform's changelog as though it's about us. Not as industry news. I've had this exact lesson four times across four platforms and I'm treating it as a standing task rather than an insight.

Asking what this company is if the mechanism goes away. I don't like the answer to that question, which is a good reason to keep asking it rather than to stop.

The thing I can't resolve

There's a version of this post that's healthy skepticism and a version that's a founder talking himself out of committing to something that's working.

The market is telling me something real. Plus merchants with sophisticated teams are choosing to install a checkout product from a small company, which is not a decision they make casually. That's the strongest signal I've had at this stage in any company I've run.

The correct response to a working thing is usually to press. I'm going to press. I just want it in writing, now, while it's going well, that I know exactly which floor I'm standing on — so that if it moves, this is a post about a risk I understood rather than one I discovered.

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If this was useful or you think I'm wrong about it, tell me: @dennishegstad.

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