Guide

Gap Selling: diagnose the gap before you sell anything

Keenan's diagnostic method: quantify the current state, establish the future state, and sell the distance between them.

Gap Selling, from Keenan's book of the same name, is diagnostic rather than persuasive. The deal is the distance between where the prospect is and where they want to be. Your product is not what you sell; the gap is what you sell, and the product is how it closes.

The pillars

Current state, quantified. Volume, frequency, cost, time. "We get a lot of tickets" is not a current state. "Three thousand a week, forty percent repetitive" is. Everything downstream depends on this number, and it has to come from them.

Future state, quantified. What good looks like, with a figure and a date. "More efficient" is not a future state.

The gap. The explicit delta. If it has not been said out loud, the rep cannot sell to it, because the prospect has not yet agreed it exists at that size.

Impact. What the gap costs, in money, time or risk. This is the difference between a problem and a funded problem.

Root cause. Why it is still broken. This is where most discovery stops one question early. Whatever they tried before, and why it failed, tells you whether you are the right answer, and occasionally tells you honestly that you are not.

Emotional impact. What it costs the person, not the company. Deals stall in procurement when nobody in the building personally needs them to close.

Decision process. Who, on what criteria, by when.

The failure it is built to catch

Selling to a gap the prospect has not agreed to. A rep who has heard "it's a bit slow" and starts presenting is selling into a gap of their own invention, and every objection that follows is really the prospect telling them the gap is not that big.

Surface-only is the interesting state

Most calls do not skip a pillar; they raise it and move on. Repwing marks that as surface-only rather than covered, because it is the cheapest fix available to a rep and the hardest to spot in your own call: at the time, it felt like you asked.

Everything on this subject

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The person who has to act on a purchase is not the same as the person who wants to buy it—and that's where deals stall.

Sales statistics

Account Executive OTE and quota benchmarks 2026

Median SaaS AE OTE is $195K with a 50/50 base-to-variable split. Enterprise AEs earn $230K–$270K+, while mid-market ranges $160K–$220K. Typical quota-to-OTE ratio is 4x–6x.

Coaching that arrives during the call, not after it

Repwing listens to your discovery calls and puts the next question on your phone while you are still in the conversation. Fourteen days free, no card.

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