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In 2018 I Closed With a Dinner. In 2025, That's Not Enough.

Enterprise selling went from convincing one champion to orchestrating 4+ invisible stakeholders. Three tactics to stop improvising and start running the deal.

Leo Giménez

Leo Giménez · CEO & Founder, Performy

Sales and human behavior expert · Sep 3, 2026 · 6 min

How deals closed in 2018, and why that's not enough today

In 2018, a dinner and a convinced champion were enough. A rep sat down with the right VP, walked through three slides of vision, and heard "sure, I'll carry it internally." Thirty days later, contract signed.

Try that today and you'll stall the moment procurement gets involved. Enterprise selling changed shape: you're no longer selling to a buyer, you're selling through them, to four or more stakeholders you'll probably never meet. And that can't be improvised anymore.

The most common mistake: the rep gets verbal buy-in from their champion... and three weeks later the deal is stuck in "budget review." Why? Because the champion never sold it internally — to Finance, to IT, to Legal.

Tactic 1: Turn your champion into an internal seller

Your champion doesn't just have to buy — they have to sell internally, with your arguments. Instead of sending a PDF they'll probably never forward, write them a short email they can pass straight to Finance or IT, with a subject line that already previews the outcome.

Subject

"Request for review — potential 18% cost reduction"

Body

"We're evaluating [vendor] to automate [process]. Early estimates show it could save 12-18% annually. If you're open to it, I'd value your take on feasibility and security — details below."

This gets read. This gets forwarded. And it sounds like it came from your buyer, not from you.

Tactic 2: A mutual plan with proof gates, not just dates

Almost every seller shares a timeline. Almost none enforce one. The difference is replacing loose dates with concrete evidence at every step.

Dates only

Week 1: security review. Week 2: stakeholder alignment. Week 3: legal.

With proof gates

Week 1: SOC2 + DPIA approved by InfoSec (via IT). Week 2: business case presented to Ops and Finance. Week 3: redlines returned by Legal.

With proof gates, if a step slips you have something concrete to ask: is this still a priority? Did something change internally? Instead of waiting in silence for the deal to reappear on its own.

Tactic 3: Pilot success criteria, agreed in writing

Plenty of pilots go well and the deal dies anyway, because nobody defined what "success" meant before starting. The rule: no pilot without a scorecard agreed in advance. Three questions before kickoff: what does success look like in 30 days, in numbers? What data proves it? Who signs off that it worked?

Then you hand their own words back to them in a simple format:

Goal

Reduce 5+ hours per week of manual work.

Metric and source

Average time saved per user, measured in the CRM and time-tracking data.

Owner

One named person on the customer's side, not an entire department.

Now you both know what "good" looks like. If anyone tries to walk it back later, the plan is already signed.

If your deal depends on one person saying yes, it's already dead.

Why this shouldn't depend on one lucky rep

None of the three tactics depend on charisma. They depend on whether the team builds coalition, evidence, and shared criteria on every big deal — or leaves it all to one enthusiastic champion and luck. It's a process decision, not a matter of one rep's individual talent.

Performy doesn't write the email to your champion or build the mutual plan for you. But it does show a manager, from the real calls, whether a rep ever asked these three questions — or whether the deal is flying blind — before it gets stuck in "budget review."

📋

Stop losing enterprise deals to ‘budget review’

Build the mutual plan with your team that turns the buyer into your internal seller — before Finance or Legal stall the deal on their own.

Leo Giménez

Leo Giménez · CEO & Founder, Performy

Sales and human behavior expert. Author of «Stop Trying to Be Someone».

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