Live coaching, out loud
Talk to Keenan about a deal that isn't moving.
This isn't a form. It's a real spoken conversation. Pick a deal that's gone quiet, describe it out loud, and Keenan will ask the questions a great sales leader would ask, then coach you on the next move in the moment. Built on Gap Selling.
- No signup to try
- A real spoken conversation
- Coaching in the moment
This live conversation is one tool from Roster, the free AI sales coach by Replicate Labs. Get the whole coach free.
Talk to Keenan about a stuck deal
Keenan, Replicate Labs' AI sales coach, will talk you through a stuck deal in a live spoken conversation. You describe a real deal that isn't moving, Keenan asks the diagnostic questions a great sales leader would ask, and coaches you on the next move in the moment, using the Gap Selling method. Most stuck deals are stuck for the same reason: the buyer never had a quantified problem worth solving now, and Keenan is built to find exactly that gap.
The problem
What everybody, including AI, gets wrong about a stuck deal
When a deal stalls, most reps blame the thing the buyer said: price, timing, a competing priority. Ask an AI and it will happily draft you a "just checking in" follow-up to chase the symptom. Both treat the stall instead of diagnosing it, and the real reason is almost always somewhere the buyer never told you to look.
Can AI coach me on a live deal?
Ask ChatGPT why your deal is stuck and you get a listicle: follow up, add value, create urgency, ask for the next step. None of it does the one thing that actually finds the answer, which is ask you the uncomfortable questions and listen to how you answer. Keenan has the real conversation out loud, probes the deal the way a sharp sales manager would, and names the gap that is actually holding it up.
Try following up with a value-add email and build some urgency around their timeline.
Walk me through it. What did the buyer say this problem was costing them, in their own numbers? And who besides your champion has said out loud that it has to get fixed this quarter?
- Was the problem ever real? Intact
- Is doing nothing free? Gap
- Is there a real why-now? Gap
- Are you talking to real power? Intact
- Is the deal single-threaded? Gap
- Did the buyer commit to anything real? Intact
The fix
What Keenan looks for
Keenan doesn't chase the stall. He works backward through the deal to find where the diagnosis broke down. These are the six things he probes for when a deal stops moving, the Gap Selling way.
- Was the problem ever real?Deals do not stall on price, they stall because the problem was never big enough to act on. If the buyer cannot name what is going wrong in their own numbers, there was never a deal.
- Is doing nothing free?If the buyer can live with this another quarter, they will. Cost of inaction is what makes the status quo hurt more than the change. No cost of inaction, no urgency.
- Is there a real why-now?A deal with no compelling event drifts forever. Something has to make this the quarter it gets solved, not someday.
- Are you talking to real power?A champion who loves you but cannot sign is not access. Know who owns the decision and the budget, and whether you have actually reached them.
- Is the deal single-threaded?One contact is one point of failure. If your champion goes quiet and no one else in the account knows why this matters, the deal goes quiet with them.
- Did the buyer commit to anything real?"Sounds great, let me loop in the team" is not a commitment. A real next yes is specific, buyer-owned, and dated. Everything else is politeness.
Reading about it only gets you so far. Bring Keenan a real deal that's stuck and talk it through out loud. He'll find the gap in the conversation itself.
How this works
This is a live, out-loud conversation, not a paste-and-score tool. Have a real deal in mind, one that has genuinely stalled, then hit the button and start talking. Keenan will ask you questions: what problem the buyer named, whether it was ever quantified, who else is in the decision, what the agreed next step was and who owns it. Answer honestly, even the uncomfortable parts. The more real you are, the sharper the coaching. Treat it like a five-minute conversation with a sales leader who actually knows the method.
Have a deal in mind? Hit start and tell Keenan what's going on.
Your conversation is recorded and transcribed so Keenan can coach you within it. It is never used to train any AI. Read our privacy policy.
This is the free product
That was Keenan on one deal. He does this on every deal you’re running.
Roster is the free AI coach behind this conversation. Bring him your live pipeline and he’ll pressure-test every stuck deal, coach your discovery calls, and sharpen your cold outbound. Unlimited, out loud or in writing. 90 seconds to start, no card.
Other ways to work with Keenan
Prefer it in writing, or on a call?
Score a real cold email or a discovery call against Keenan’s method, then land on the leaderboard. The sharpest cold email and the sharpest discovery call each win a signed set of all three of Keenan’s books: Gap Selling, Gap Prospecting, and Gap Enablement.
The coach behind the model
Keenan didn't win by accident. He wrote the method the others were trying to imitate.
Keenan is the creator of Gap Selling, the problem-centric sales methodology that changed how a generation of B2B teams sells. His bestselling books, Gap Selling and Gap Prospecting, became required reading inside sales orgs from early-stage startups to the Fortune 25, and Gap Enablement is releasing soon.
He has spent 37 years in sales and built A Sales Guy into one of the most recognized names in the field. Forbes named him one of the top 30 social sellers in the world. Top Sales World has named him one of the 50 most influential people in sales and marketing every year since 2012. His thinking shows up in Forbes, Harvard Business Review, Inc., and Fast Company.
When we built our AI sales coach, we didn't train it on generic best practices. We built it on Keenan's method. That is why, when six models wrote a cold email and buyers judged blind, the one built on the method beat the ones built on everything.
Client-reported results from Keenan's methodology.
Forbes Top 30 Social Sellers in the World
Top Sales World Top 50 in Sales & Marketing, every year since 2012
Testimonials
In their words
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I thought it would be a ChatGPT clone of Keenan who would give surface-level advice. I don’t think I have ever been this wrong in my life. It surfaced behavioural patterns I didn’t know I had. Higher pipeline, less ghosting, better discovery.
Abdullah Sajjad Sales Professional -
Got early access this week and wow, I wasn’t ready for how intense it would be. It doesn’t just coach you, it challenges everything you think you know about your deals. Called me out on assumptions within minutes.
Christopher Carlton Major Account Executive, Thales -
Keenan AI just helped me unstick my largest renewal this quarter. What I was missing was the why behind the metric. Implemented the learning on the call 30 minutes later and we’re miles closer to the CEO.
Nate Hippauf Sales Professional, Common Room -
He asked me questions I couldn’t answer. Basic ones. The kind that make you realise you’ve been guessing at things you should actually know. Humbling. Useful. Worth every minute.
Lee Chandler Sales Professional -
Built specifically for sales: deal review, strategy, roleplay, pre-call planning, sharpening execution. Pushes honest self-reflection by challenging your approach in real time. Practical instead of generic.
Brandon Hawkins Key Account Manager -
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 Green DME Solution Consulting Manager
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