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Get Keenan As Your Coach

24/7 on-demand coaching with Keenan. Built from Gap Selling. Get real feedback, run roleplays, fix your pipeline.

Get Keenan As Your Coach

24/7 on-demand coaching with Keenan. Built from Gap Selling. Get real feedback, run roleplays, fix your pipeline.

People We Work With:

You know you could be better. You just lack the guidance.

Deals get pushed to next Q.

Everything seems fine, but deals aren’t closing. No one reviews what’s happening, so you miss the critical deal elements.

  • Your sales cycle gets extended
  • Your competition sneaks in
  • Your forecast is missed

You got ghosted. Again.

Everything seemed to be going well, then silence. Nobody to help you understand why it went cold and how to fix it.

  • Your deal stalls without warning
  • You chase instead of qualify
  • You’re stuck in a hamster wheel

You’re Losing to the status quo.

The problem is real, but not urgent enough. Without help, you don’t challenge the buyer’s inertia or build a compelling reason to act now.

  • Your deals slip into “later”
  • Your value gets forgotten
  • You lose to no decision

They say they love it, but don’t buy.

You get great feedback, but no commitment. Stakeholders smile, nod, and then… nothing. You need help to build urgency.

  • You can’t secure a decision
  • You over-commit your forecast
  • Your win rates take the hit

“Even Tiger Woods had a coach. The greatest understand the power of coaching.

– Keenan

Now you’ve got Keenan in your pocket…

Every Call Reviewed

No random Gong homework your manager doesn’t do. Get the help you need.

 

  • Identify discovery gaps
  • Recommend next-best actions
  • Diagnose the core problem

Quick Answers to Anything

Stuck? Don’t wait on Slack. Get answers instantly no matter the ask, 24/7

 

  • Fix stuck or stalled deals
  • Improve deal-related messaging
  • Create urgency when it’s missing

A Strategic Partner

Stop being reactive. A mentor helping you plan ahead, build skill, execute better.

 

  • Prioritize what buyers actually value
  • Build long-term selling skills
  • Shift from pitching to helping

Honest, Unbiased Feedback

No politics, no favoritism, no laziness, but also no holding back.

 

  • Get direct, unfiltered coaching
  • Build awareness of blind spots
  • Grow confidence through real skill

Meet Your Coach. Not a Chatbot.

AI Keenan is built from everything Keenan has ever taught, trained, coached, and called out.

Keenan will review your calls

Keenan flags what you skipped, where you lost the buyer, and how to fix it next time. No generic feedback in sight.

  • Missed pain? He’ll surface it.
  • Rushed the close? He’ll slow you down.
  • Just rambled? He’ll call it out.

Keenan will improve your emails

Keenan helps you rewrite cold emails, tighten follow-ups, and craft messaging that lands. You don’t get a template, you get tactical coaching on what to change.

  • Coaching, not a vending machine
  • Centered around the buyer’s problems
  • Emails that make buyers respond

Keenan will help you practice

You don’t get better by reading. You get better by doing. Keenan runs drills, exercises and full-call roleplays, tailored to your world and what you’re trying to improve.

  • Sessions that match your real buyers, not made-up ones
  • Coaching points specific to you
  • Targeted, efficient, worthy of your time

Keenan will make you improve

Coaching that tracks your performance. For real. You’ll see your discovery sharpen. Your deals move faster. The mistakes you used to make? Gone.

  • Skills progress over time
  • Weekly reports
  • Every insight ties back to pipeline. Not vanity.

One coach. Two ways to use him.

Pick your mode and switch anytime

A.K.A. Mode

Ask. Keenan. Anything.

 

What it offers:

 

  • Get instant answers, anytime
  • Rewrite emails and outreach
  • Prep fast for demos or calls
  • Fix stuck or ghosted deals
  • Get tactical help, no structure

Gap Mode

Keenan Leads. You Grow.

 

What it offers:

 

  • Build real sales fundamentals
  • Follow a structured coaching plan
  • Practice discovery and qualification daily
  • Track progress with drills and scorecards
  • A proven system to level up

Most AI coaching tools do zero actual coaching

Simulated roleplay ≠ real coaching. Here’s the difference

Feature Typical ‘AI Coaching’ Tool AI Keenan
Role — Simulated buyer persona ✓ Personal AI sales coach
Interaction — Reactive only ✓ Diagnoses, instructs, challenges
Context — One-size-fits-all ✓ Your deals, your personas
Learning — Generic responses ✓ Built on Gap Selling
Feedback — None or shallow ✓ Deep feedback + follow-up
Memory — Forgets your history ✓ Tracks your progress

When you get coached by Keenan, everything changes

⭐⭐⭐⭐⭐

“Keenan has high energy and is a straight to the point coach. This is mind-opening sales strategy

Alina
BDE
G2 Review
⭐⭐⭐⭐⭐

This will change the way you sell forever! It’s obvious that our organization is doing the wrong things to drive sales.”

Mid-market AE
G2 Review
⭐⭐⭐⭐⭐

“Keenan is direct and entertaining too. I walked away feeling smarter and more confident

Kasey
Sales Director
G2 Review

Get coached. Get better.

You don’t need another tool. You need a coach.

Includes:
“I’m a Gap Selling badass” t-shirt
50% off Gap Plus, Keenan’s best courses and private webinars

or

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