If you’re trying to rip out an incumbent vendor, you’re not just selling a product.
You’re selling a divorce.

And divorces? They’re painful.
They’re messy. Emotional. Risky. 💔

Which is exactly why so many deals stall when prospects get cold feet—even when the current solution sucks.

That outdated, overpriced, inefficient system they’re clinging to? It’s familiar. And familiarity feels safer than change, even when it’s actively holding them back. 😬

Great reps understand this.
They don’t just pitch a better product.
They make staying put feel more dangerous than moving forward. ⚠️

1. Quantify the Hidden Costs 💸

Legacy vendors often survive because their costs seem predictable.
But reps need to expose the real cost of staying—and make it hurt:

  • Lost productivity due to inefficient workflows

  • Poor integrations that create downstream rework

  • Security risks no one’s talking about 🔓

  • Opportunity cost from slow innovation 🚫

Don’t just say, “We’re better.”
Show them how much it’s costing them not to switch.

2. Sell Leadership on Future-Proofing 🚀

Executives aren’t buying features.
They’re buying strategy insurance. 🛡️

They want to know: Will this system support where we’re going in 3, 5, 10 years?

Make the current vendor look like a blocker to growth—not just a legacy tool.

3. Make Switching Painless 🛠️

This is where deals live or die.

Because if your migration or onboarding plan feels risky, you’re dead in the water—no matter how compelling your product is. 🪦

You need a bulletproof transition plan.

4. Find the Internal Frustrations 😤

Here’s the secret most reps miss:
End users hate legacy systems.

They’re clunky. Slow. Built for a business model that died a decade ago.

Make life easier for the people in the trenches, and they’ll become your internal champions, pushing for the switch from the inside out. 🙌

The Real Truth: People Don’t Leave Vendors. They Leave Situations.

This isn’t just about a better feature set.
It’s about creating urgency by painting the cost of inaction.

If staying put feels safe, they won’t move.
But if staying feels dangerous—like they’re betting the future of the business on a crumbling foundation—change becomes the only logical choice.

You’re not selling software.
You’re selling escape. 🏃‍♂️💨

About Sales Assembly

We’re a resource for live, year-round skill development and certifications for the core roles within b2b revenue teams.  Contact us to explore membership options for your organization!