October 25, 2025 | Read online

Why Your Best Reps Keep Losing Winnable Deals

by Kevin 'KD' Dorsey

There’s a painful pattern I see in sales orgs - especially right now.

A rep nails the discovery. The demo is crisp. The buying team is engaged. Everyone’s nodding along like this thing is a done deal.

But then… weeks pass.

Follow-ups go unanswered. Internal priorities “shift.” The champion goes dark.

And just like that, another winnable deal dies a slow, silent death.

Most leaders chalk this up to the usual suspects - bad product fit, pricing, lack of urgency.

But more often than not, those aren’t the real culprits.

The problem? No one ever taught that rep how to manage the deal.

Selling is not Managing

We spend so much time teaching salespeople how to sell—but very little time teaching them how to manage the sale.

And y’all… they’re not the same thing.

Selling is what happens during the demo.
Managing is what happens between the demo and the signature.

And the skill gap between the two? It’s a silent killer.

Because here’s what I’ve learned over the last decade leading and coaching thousands of sellers:

I don’t care if you run MEDDIC, Challenger, BANT, SPICED, or CTM.

If your team doesn’t know how to manage a deal, it’s not gonna close.

Period.

What Great Deal Management Looks Like

It’s not about new acronyms or fancy frameworks. It’s about mastering the boring stuff that most teams ignore:

– Booking next steps that prospects actually attend
– Sending follow-ups that add real value (not “just checking in”)
– Multi-threading with intent, not just collecting LinkedIn connections
– Keeping momentum high through every stage of the deal

This isn’t rocket science - but it is a science. And it’s one most teams aren’t teaching.

You can’t afford to skip it.

That’s why I’m speaking at Consensus’s RevAMP Conference on November 5th.

My session’s called:

“The Lost Art of Deal Management: How to 2X Your Close Rates Without Changing Your Methodology.”

I’m going deep on the tactical side of keeping deals alive and moving—from first “yes” to final signature.

You’ll walk away with:

✅ A proven playbook for managing mid-funnel momentum
✅ Specific tactics to avoid deal stall-outs
✅ My personal Deal Management Checklist (the one I’ve used to drive 9-figure outcomes across teams)

Not a template. Not theory. The real checklist.

If you're tired of watching good deals go cold…

If you know your team is better than what the numbers are showing…

If you’re ready to fix what’s actually broken in your sales process…

Then you’ll want to be in the (virtual) room.

👉 Click here to save your seat

See you at RevAMP.

– KD