On the Table

What I look for in the first two weeks inside a new company

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When I step into a new company, I don't walk in with a template and start applying it. I've learned that the fastest way to build the wrong motion is to assume you already know what this company needs. So the first two weeks are diagnosis, and almost nothing else. Here's what I'm actually looking for, because it's the same thing any founder can start looking for in their own sales.

I start in the deals, not the deck

The strategy doc tells you what the company believes about its sales. The deals show you what's actually true. So I go straight to the real thing: recorded calls, the live pipeline, the deals that closed and the ones that quietly didn't. I want to hear how buyers actually talk about the product, where their questions get sharp, and the exact moments a conversation loses energy. You learn more from one stalled deal than from a whole quarter of clean dashboards.

I'm hunting for where trust breaks

I watch for the places trust starts leaking: the late follow-up, the over-smooth answer, the moment a seller reached for pressure instead of sitting with a buyer's hesitation. Trust erosion is usually the first thing to sink a deal and the last thing anyone's measuring, so it's the first thing I map.

I'm reading what only lives in the founder's head

This is the big one. In a founder-led company, most of what makes sales work is unwritten, sitting in the founder's instincts. How they qualify without realizing they're qualifying. The pricing logic they improvise. The read on which buyer is real and which one is wasting everyone's time. My job in the first weeks is to pull as much of that into the open as I can, because a motion can't be built on things only one person knows.

I'm looking for the gaps in the middle

I map the unglamorous parts where deals slip: follow-up that isn't scheduled, trials with no success criteria, the pricing conversation everyone avoids, the handoffs where context falls on the floor. These are boring, and they're where most of the lost revenue actually lives.

I'm watching how the founder sells

I watch how the founder sells so I can keep the parts that already work. Founders are almost always doing several things right on pure instinct, and those things are the seeds of the motion. I also get clear early on where the line sits: the founder stays the technical authority and the face of the company, and I carry the commercial weight. Knowing that line from day one is what keeps the whole thing from turning into a tug of war.

Why it's diagnosis first, always

You can't prescribe a motion you haven't diagnosed. Every company's buyers, sales cycle, and failure points are a little different, and the fastest way to waste an engagement is to arrive with someone else's playbook and force-fit it. The two weeks of listening are what make everything after it fit, because the motion gets built around your actual deals instead of a generic idea of them.

That's also why none of this is templated. What I build for you is shaped by what those first two weeks turn up, which is the only way it holds once I step back.

If you're curious what a fresh set of eyes would find in your sales in two weeks, that's a good reason to book a free strategy session.