Why I stopped apologizing for deal-driven product work

The features I've built to close deals were some of the most valuable ones I shipped—and it took me far too long to realize it. It's something I want people to hear, especially early-career ICs who didn't land in enterprise on purpose, but started out with a consumer mindset.

Most of what gets written and said about tech comes from that world. So when an executive asks you to build something to close one, maybe two or three six-figure deals, it feels wrong, like something went off track. We think, shouldn't we be discovering opportunities that serve a much larger swath of customers? And we do. But in enterprise, that can't be the whole roadmap.

It's natural to think the customer should be interested in buying the product as-is, and maybe we'll address their additional needs later if enough people say the same thing. But when the deal is six or seven figures, they're allowed to point out what's missing before they sign, and it's not professional services to do it. The customer is buying what you've built—but the request is part of a larger motion that was set in place by the strategy we executed earlier. We earned the pipeline through smart product decisions. Sometimes, closing it means building what's still missing.

I didn't understand this at first. I look back on earlier parts of my career and wish I could help myself, and my team, see it more clearly. (This article by Patrick Morgan would have come in handy!) Instead, I was aligned with the engineers, who had reservations about deal work. There was a time where my engineering manager and I stalled a feasibility study for six weeks, thinking we could convince leadership not to build the thing. When we finally shipped it months later, it worked beautifully. It was complex, yes, but high-leverage, and the revenue justified it completely.

Deal-driven work isn't always fun, because it can feel like order-taking. But you're not building the feature they asked for to merely to give a few customers VIP treatment, but because of the reality that sometimes they won't even become a customer without it. The difference can be hard to wrap your head around. But it's real, and the outcomes are measurable.

I may have hesitated before, but I'm not sorry anymore, I'm proud of it.