AI Sales Coaching
See what your
deals are missing.
Built For:
Stuck Deals • Ghosted Buyers • Outbound Sequences • Pipeline Risk
Support for every piece of your sales process
An AI sales coach built on Gap Selling, on call 24/7 to show you where each deal is weak, what you still don’t know, and what to do next — from tightening discovery to writing outbound buyers can’t ignore.
"I work deals for months and never see them close"
"My close dates keep moving and I don't know why"
"I can't get a single prospect to respond"
"My pipeline looks healthy but I'm behind every month"
Support for every piece of your sales process
An AI sales coach built on Gap Selling, on call 24/7 to show you where each deal is weak, what you still don’t know, and what to do next — from tightening discovery to writing outbound buyers can’t ignore.
"I work deals for months and never see them close"
"My close dates keep moving and I don't know why"
"I can't get a single prospect to respond"
"My pipeline looks healthy but I'm behind every month"
Sell like the Top 1%.
Built on Gap Selling and Gap Prospecting, wired into the tools you already use.
It reads your deals, emails, and calls, spots where you’re missing critical information, and tells you exactly what to do next to move the buyer. It gives you expert help creating intrigue and interest from cold calls and cold emails, so your outbound actually gets responses and books meetings.
As it sees patterns repeat across your pipeline, it turns those into focused coaching sessions, talk tracks, and practice reps you can run on demand.
Close deals faster.
See what’s missing in your deals, uncover the risks you don’t see, and get a clear plan to move them forward.
Get ghosted buyers back.
See why your buyer went quiet, uncover what you missed, and get a clear way to re-engage.
Talk to your buyer before every call.
Test your approach, pressure-test your questions, and walk in knowing exactly how the conversation should go.
Stop getting ignored.
Give buyers a reason to respond with messages built around what they actually care about.
Sell like the Top 1%.
Built on Gap Selling and Gap Prospecting, wired into the tools you already use.
It reads your deals, emails, and calls, spots where you’re missing critical information, and tells you exactly what to do next to move the buyer. It gives you expert help creating intrigue and interest from cold calls and cold emails, so your outbound actually gets responses and books meetings.
As it sees patterns repeat across your pipeline, it turns those into focused coaching sessions, talk tracks, and practice reps you can run on demand.
Close deals faster.
See what’s missing in your deals, uncover the risks you don’t see, and get a clear plan to move them forward.
Get ghosted buyers back.
See why your buyer went quiet, uncover what you missed, and get a clear way to re-engage.
Talk to your buyer before every call.
Test your approach, pressure-test your questions, and walk in knowing exactly how the conversation should go.
Stop getting ignored.
Give buyers a reason to respond with messages built around what they actually care about.
What Customers Are Saying
“It’s been incredible in ways I never would have expected”
“He actively blocks you from being lazy.”
“Left the session with specific action items, a deadline, and three numbers I need to go get the buyer”
Built to move deals, not just answer prompts.
If you’d throw your manager at it, you can throw AI Keenan at it.
| You say | Generic AI gives you | AI Keenan gives you |
|---|---|---|
| “This deal has been stuck for 60 days.” | Tips about following up and “adding value.” | A breakdown of what you haven’t validated, where the gap is weak, and the next move to restart the deal. |
| “This buyer ghosted me after the demo.” | A polite re‑engagement email and reminders to “stay persistent.” | A likely root cause based on what’s missing in their business case and world, plus questions to reopen and reset the problem and impacts. |
| “No one responds to this outbound email.” | Surface‑level rewrites focused on being shorter or more catchy. | A version that creates immediate interest by locking onto the failure pattern and stakes in the buyer’s environment, so you earn the meeting. |
| “I don’t know if this is a real opportunity.” | Asks if your buyer has budget, authority, need, and timing—and considers it qualified. | A pointed read on whether it’s real, what’s missing in your discovery, and what to ask before it ever hits Commit. |
| “My pipeline is full, but I’m still behind quota.” | Tells you to expand your pipeline or improve your sales process, without clear steps. | A view of which deals are real vs. bloated, which are in danger, and where to focus your time so you stop wasting it on fake pipeline. |
From the mind behind Gap Selling
Keenan has spent decades in the trenches with sales teams, from scrappy startups to global enterprises, changing how they think about problems, impact, and pipeline reality. This product is built from that work, so when you plug a deal, buyer, or sequence into it, you’re getting that same hard-nosed thinking pointed at your pipeline.
Instead of a one‑off workshop you forget in a week, it’s a way to keep that pressure and perspective on every opportunity you care about.
Author of Gap Selling and Gap Prospecting. Founder of A Sales Growth Company.
GapUp AI Sales Coaching FAQs
What do I need to get value?
One real deal or outbound thread and a few minutes. Paste what you have, ask what you’d ask a strong manager, and test the plan on your next touch.
Do I have to change my whole process?
No. Keep your CRM, cadence, and tools. Use this when a deal stalls, a buyer disappears, or your outbound isn’t landing.
Is this just another generic AI chat?
No. It’s an AI sales coach built on Gap Selling and Gap Prospecting, trained on hundreds of hours of Keenan’s coaching and deal reviews, and tuned to push on real gaps, real risk, and real next steps.
How long does it take to see if it works?
One deal, one buyer, or one outbound sequence. Most reps know it’s helping after a single test.
Will it replace my manager or enablement team?
Try it Free.
Grab one stubborn deal, one silent buyer, or one outbound sequence that’s going nowhere. Give it to AI Keenan, let him tell you what’s missing, and what you need to do next.