Use case · Deal execution
Coach the deal in front of you.
The deal that surprises you at quarter-end had a signal weeks earlier. Keenan works the live deal with you: what's missing, what the next move is, where it's quietly stalling.
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Overview
Drive deal execution is the use case of getting a specific, live deal moving again. It is the single most common reason reps open Keenan: roughly one in twenty coaching conversations is a rep evaluating a tactical choice on a real opportunity. You describe the deal in plain English (the buyer, the stage, what was said, what feels off) and Keenan coaches it the way a sharp manager would in a one-to-one. He does not summarise your CRM back to you. He diagnoses the gap between where the deal is and where it needs to be, names what is unconfirmed, and gives you one move to make next, with the reason it is the right one. Keenan is built on Gap Selling, so the diagnosis always comes back to the same question: is the buyer's problem named, and is its cost quantified? If it is not, the deal is a meeting, and he will say so.
The jobs
What reps actually bring to it.
Each one is a real job, drawn from how sales teams use the coach. Bring yours, and Keenan works it with you.
- 01
Pressure-test a tactical choice before you commit
"Here is my plan, does this make sense?" Get a second read before the move is live.
This is the most frequent deal-coaching job: a rep has decided to do something (send the proposal now, push for a meeting with the VP, hold firm on price) and wants a check before it goes out. Keenan asks what you are trying to achieve with the move and what the buyer has actually confirmed, then plays out the likely response. Either you go ahead with more conviction, or you catch that the move assumes a problem the buyer never agreed they had, and you fix the discovery gap first instead of burning the touchpoint.
- 02
Unstick a stalled or losing deal
Find what is actually holding it, and the action that re-opens it.
A deal that has not moved in three weeks is rarely stuck for the reason in the CRM note. Keenan works backwards from the last real moment of progress and asks what changed: did a stakeholder go quiet, did the problem stop feeling urgent, did you never quantify the cost of inaction. He separates a deal that is dead from one that is dormant, and for the dormant one gives you a concrete re-opening move tied to the buyer's situation, not a generic nudge. Get this right and you know whether to invest or walk. And if you invest, you carry a real reason for the buyer to re-engage.
- 03
Read the real health of a deal
Past the CRM stage: what is confirmed, what is missing, what to do about it.
Stage in the CRM tells you where the deal is supposed to be. It does not tell you whether the buyer can name their problem in numbers, whether the economic buyer has been in a room, or whether anyone has agreed a future state. Keenan runs the deal against the parts of your methodology that actually predict close: problem clarity, quantified impact, access to power, a compelling reason to act. He returns a short, honest read of what is solid and what is assumed. Done well, your forecast category reflects reality and you walk away with the one or two gaps to close before the next call.
- 04
Find the right next step
Decide the one move that advances the deal instead of stalling it.
Reps often have five things they could do next and no clear sense of which one moves the deal. Keenan does not hand you a checklist. He asks what the buyer needs to believe or decide for the deal to progress, then names the single next step that creates that, plus what a good version of it looks like. A 'next step' that is just another meeting with no decision attached is not a next step, and he will push back on it. You leave with one move, the reason it matters, and a way to tell whether it landed.
- 05
Navigate a multi-stakeholder deal
Map the org, multi-thread, and reach the economic buyer.
Complex deals die in the gap between the person you talk to and the person who signs. Keenan helps you map who is involved: who has the problem, who controls the budget, who can block, who you have never met. He coaches the multi-thread, how to use your champion to get access rather than going around them, and what each stakeholder needs to hear in their own terms. Run it well and you have named every stakeholder who can kill the deal, you have a credible path to the economic buyer, and your champion is helping you build it.
- 06
Write the follow-up that re-opens a quiet deal
Re-engagement that earns a reply, not another ignored nudge.
Post-meeting and post-call follow-up is one of the highest-volume jobs reps bring to Keenan. The default 'just circling back' email gets ignored because it gives the buyer nothing new to react to. Keenan reads what was actually discussed, finds the open loop or the unresolved problem, and drafts a follow-up that puts that in front of the buyer and asks for a specific, small decision. The result is an email that references the buyer's own words, advances one thing, and is short enough to answer from a phone.
- 07
Qualify and score the deal honestly
Run it against your methodology and surface what is not really there.
Qualification fails when it becomes a box-ticking exercise the rep does to themselves. Keenan runs your deal against your qualification framework (MEDDPICC, MEDDIC, or Gap-based qualification) and is deliberately unforgiving about the difference between 'I think' and 'the buyer told me'. He surfaces the criteria you are scoring on hope. What you end up with is a qualification read you would defend in a pipeline review, and a clear call on whether this deal earns more of your time.
- 08
Recover after the proposal went silent
A move for the deal that has gone dark since you sent pricing.
Silence after a proposal usually means the value case did not survive contact with the people who were not in the room. Keenan helps you work out the likely reason (the price landed without the cost-of-inaction beside it, an unseen stakeholder pushed back, a competing priority won) and gives you a recovery move matched to that reason. Instead of a third 'any update?' email, you re-open the conversation about the problem and its cost: the only ground where the proposal can be defended.
The bar
What good looks like.
Not the theory. The concrete signs you are running this use case well.
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Every deal in your commit category has a problem the buyer has named in their own numbers, and you can repeat that number back without checking your notes.
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When a deal stalls you can say why within a day, because you have already worked it through with Keenan rather than waiting for the pipeline review to expose it.
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Your next steps are decisions, not meetings. Every forward motion in the deal has something the buyer agreed to attached to it.
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Quarter-end holds no surprises in either direction: the deals you called are the deals that landed, because the forecast was built on confirmed facts not optimism.
FAQ
Quick answers.
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Do I need to connect my CRM for deal coaching to work?
No. Keenan coaches on what you tell him in plain English, so you can work a deal without connecting anything. On Team and Enterprise plans you can connect Salesforce or HubSpot so Keenan has the deal context without you retyping it, but the coaching itself does not depend on it. The free tier is conversation-only and still works for a live deal. -
Can Keenan see my actual pipeline and forecast?
Keenan coaches one deal at a time, in conversation with you. He is not a pipeline dashboard. If you want an AI manager that reads across every deal and call to surface team-wide drift and prepare the forecast read, that is Bryce, the RevOps coach, included as standard on Team and Enterprise plans. -
Will Keenan just tell me what I want to hear?
No, and that is the point. Keenan is built on Gap Selling: if the buyer's problem is not named and the impact is not quantified, he will tell you that you have a meeting, not a deal. He is deliberately unforgiving about the difference between what you assume and what the buyer has actually confirmed. -
My team uses MEDDPICC, not Gap Selling. Can Keenan still coach my deals?
Yes. Keenan's core is Gap Selling, but if you ask he will coach your deal against MEDDPICC, MEDDIC, or SPIN alongside it, qualifying and scoring against your framework. If you want a coach whose primary methodology is MEDDPICC or a custom playbook, that is Caty, available on Enterprise. -
How is this different from logging the deal in my CRM?
Your CRM records what stage the deal is in. Keenan tells you whether that stage is real, what is missing, and what to do next. It is the difference between a system of record and a manager who works the deal with you.
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