What is Gap Prospecting?

Gap Prospecting is the cold-outreach method for earning a reply and starting a conversation. It orients the whole email around the buyer’s problem and its root cause, not your product. The subject and opening make the first sale (intrigue), the body makes the second (pain relief), the proof is forensic (what you found inside a peer company), and the ask offers insight. The meeting comes after they reply.

What does the cold-email score measure?

It measures how faithfully your email follows Gap Prospecting across eight weighted dimensions: problem-first framing, the crack and redefine, forensic proof, root-cause intrigue, future connection, CTA discipline, relevance, and format. The score is directional fidelity to the method. It is not a predicted reply rate.

Does it rewrite my email?

No. This tool is a diagnostic. It names the single gap costing you the most. The rewrite is a conversation with Keenan, where he asks what the email is for and explains why every line changed.

Is my email kept private?

Yes. Every email is anonymised before Keenan reads it: names, companies and contact details are stripped in memory and never stored. It is never used to train any AI.

What if I paste something that is not a cold email?

Keenan will say so and it will not cost you a score. The scorer reads one thing: a cold first-touch email selling to a buyer with a business problem. A partnership proposal, a reply or a recruiting note gets an explanation and an offer to work on it with him instead.

Gap Score · specimen email

54 of 100. The product arrived before her problem did.

Keenan · scored on Gap Prospecting

Biggest gap: it grabbed the meeting before earning the reply.

Score my cold email · for SDRs and AEs who write their own

Would the buyer reply to this? Keenan scores it before you send.

Keenan wrote Gap Prospecting. Paste the cold email you are about to send and he reads it the way the buyer will, scores it out of 100 against the method, and names the one gap costing you most. Three scores, no signup.

Score my cold email Score a discovery call instead

Anonymised before he reads it. Names, companies and contacts stripped in memory, never stored, never used to train any AI.

What Keenan looks for

Six things a reply depends on.

The score is fidelity to Gap Prospecting, the method Keenan wrote for earning a reply. Every dimension is a question the buyer answers in the first four seconds. Below, a specimen email marked on the six principles. The live score breaks them into eight weighted dimensions.

Specimen email, marked for scale. Yours is scored live above. Gap Score

54/100

Meeting-grab

Found an angle on the buyer’s problem, then introduced the product and asked for Thursday. Every line after the opener is about the sender.

Score yours

Problem before product70

Lead with the buyer’s problem. If your product is the first thing they meet, you’re already deleted.
Redefine their reality60

Say the one thing they haven’t considered. Take the problem they think they understand and give it a name that makes them stop.
Proof, not claims42

Show what you found inside a real company: three specifics and at least one number.
Open a loop, don’t label it66

A subject line should leave a question in their head. "Improving forecast accuracy" is a label. "The deals under your forecast" is a loop.
Connect it to what’s next58

Tie the problem to something they’re about to walk into, so it lands as a live threat.
Earn the reply, don’t grab the meetingBiggest gap31

Offer something useful they can say yes to in one word. The meeting comes after they answer.

After the score · Do

The rewrite is a conversation. He asks what the email is for.

The score tells you where the email leaks. The rewrite happens in conversation with Keenan, where he cuts the line that sells before it earns and adds the question the buyer can answer in one word. Talk it through with him; if you cannot talk, type.

The email, judged before it leaves. Your draft or a model’s. Scored against Gap Prospecting, then rebuilt around her problem.
The proof line, found for you. Three specifics and a number from a peer company.
The sequence, read as a whole. Five touches that open one loop and keep it open.

Builder: put the coach’s judgement inside your own outbound agent, so every reply is judged before it leaves

To Dana Whitfield · Halden Foods

Quick intro from Northstar

Hi Dana, you mentioned at the ops roundtable that the four sites still re-key orders by hand.

I’m with Northstar, a revenue intelligence platform that helps teams record calls, analyse deal risk and improve forecast accuracy. Worth a quick call to see if it’s a fit? Would Thursday or Friday work?

Inside a peer with five sites, the re-keying was costing 31 hours a week before anyone counted it. What does it cost yours?

Gap Score · after the rewrite81 of 100Problem first. Proof with a number. A one-word reply to earn.

Keenan: don’t send it yet.Dana meets your product before a single problem of hers. She files you as a salesperson and deletes it. Lead with what the re-keying costs, and the meeting comes after she answers.

Deleted in four seconds.

A buyer decides whether to reply before the end of the second line. Most cold email loses there, and a general model scores it kindly because it has no method to hold the draft against. Keenan does.

01
Product before problem.
The first thing the buyer meets is your company and a feature list, so her brain files you under salesperson.
Deleted before a problem of hers appears.
02
A claim where the proof should be.
"Companies like yours see results in the first month" is a sentence she has read nine hundred times.
Nothing in it she could go and check.
03
The meeting before the reply.
"Would Thursday or Friday work?" asks for twenty minutes before earning one word.
The reply rate lives in the ask.

Leaderboard

The sharpest cold emails, scored by Keenan

Top the board, win the signed set.

The sharpest cold email and the sharpest discovery call each win a signed set of Keenan’s three books: Gap Selling, Gap Prospecting and Gap Enablement. Whoever is on top when the competition closes takes the set.

The board is open.

No entries yet. Score your cold email and opt in to take the top spot.

There is a discovery call board too

His email won the blind read. Five judges, none of them ours.

14 of 15

Blind verdicts favoured Keenan’s cold email over five frontier models writing from the same brief. Five independent model judges, three buyer personas each, both of Keenan’s own judge seats excluded. The frontier models were asked cold, with no system prompt; Keenan ran as it ships, with the method installed. That asymmetry is what the study measures, and the scorer above holds your email to the same method.

Read the study, every email published

votes for four of the five frontier models

GPT-5.5, GPT-5.2, Gemini 3.1 and Claude Sonnet 4.6 opened with "saw your post", pitched by line three and asked for twenty minutes. No buyer picked one.

Email LLM Benchmark · May 2026 · self-judge seats excluded

free scores here, then the coaching

The scorer is one instrument. Working a live send with Keenan is the other: he scores it, rewrites it with you and reads the whole sequence.

Three scores per visitor · no signup

A rep whose emails got called out

Rep

Takes the concepts in Gap Selling and applies them to real deals. It calls me out on prospecting emails I think are clever. A colleague said it opened blood flow to a part of his brain he didn’t know existed.

Michael GreenDME Solution Consulting Manager

Bring the email you were about to send. Keenan reads it before the buyer does.

Three scores here, no signup. After that the rewrite is a conversation: bring him a live send, or talk to Keenan about a deal that has gone quiet.

Bring us a live send