Founders and CEOs who shouldn’t be the sales department.
Selling into the enterprise. The founder is still doing most of the selling. There is no true VP of Sales in the building.
Complex technology into the enterprise — any vertical that buys that way.
eCommerce / OMS · AI & computer vision · Robotics · Other enterprise-sold tech. Those are examples, not a gate. The enterprise sale is the gate.
Enterprises that buy through processes and committees
The VP with the problem, IT, the CTO, InfoSec, finance, procurement. A pilot before a rollout. An RFP when you least want one. A partner ecosystem that decides who gets in the door.
I’ve sat across those tables for thirty years — same enterprise motion, any vertical that buys that way. Kroger, Procter & Gamble, Luxottica, Abercrombie & Fitch, Bass Pro Shops from the vendor side. Toshiba’s single largest client globally from inside the retailer’s own technology headquarters.
The founder is still the sales department.
Companies in a product pivot. Companies moving upmarket that have hired one or two sellers who aren’t yet winning.
It’s a fit if
- The founder is in every deal that closes — and out of every deal that doesn’t.
- Your deals are complex: multiple stakeholders, a security review, sometimes an RFP.
- You have a pilot or two and no repeatable path from pilot to rollout.
- You’re deciding whether to hire a VP of Sales and would rather know before you spend a full-time salary finding out.
It isn’t if
- You want a lead-generation agency or an outsourced SDR team.
- You sell a low-touch product that doesn’t need an enterprise process to buy it.
- You want a workshop and a deck.
Investors, boards and CFOs
If you sit on the board or hold the check, a consultancy engagement or a market-position review gives you an independent read on the sales function — in numbers, not adjectives.
Exhibiting at Shoptalk Fall or NRF’s Big Show?
You’re exactly the founder and CEO I’m looking to meet. Want to get your company off the floor in record time? You should be working with someone like me. Let’s talk.