🦾 the enterprise formula

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• Large deals win

• Large deals magic

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Build efficiency to prevent stalled deals

Troy Munson breaks down how large enterprise deals move differently than others.

Here are 10 lessons from deals over $500k that any rep can use to win deals:

1. Test your champion

A champion who can’t move things internally isn’t really a champion.

💡 Ask them to get higher-ups on a call

💡 Ask for better, quicker procurement

💡 Get your legal teams involved early

➤ Example: In one $700k deal, my “champion” wouldn’t intro me to the CFOs. That response told me they lacked influence, so I found another.

True champions act, not just talk.

2. Create your fanbase

One champion isn’t enough - you need a bench.

💡 Engage people being involved

💡 Address their concerns directly

💡 Use everyone’s input as ammo

💡 Feed them with relevant data

➤ Example: I sent a case study to an operations manager. She later repeated everything to her VP, becoming an advocate. Fans multiply your winning odds.

3. Neutralize the blocker

There’s always someone blocking your progress.

💡 Learn why (often tied to competitor)

💡 Expose current gaps in their position

➤ Example: A director preferred a competitor. I asked how they managed key integrations. He admitted they couldn’t, and his stance weakened.

4. Establish connections

Big deals move faster outside of email.

💡 Do this with your champion and with legal/procurement

➤ Example: Procurement texted me updates in a $500k+ deal. That relationship-building investment helped me keep our executives aligned.

5. Don’t negotiate early

Pricing too soon kills your leverage.

💡 Biggest deals often have the smallest discounts

💡 Stand firm until you’re their main chosen vendor

➤ Example: I refused an early discount request. We later closed at list price.

6. Stripline negotiations

💡 Pushbacks might reset your leverage.

➤ Example: In a $900k deal, procurement said a competitor was cheaper. I replied:

“If they’re still an option, maybe we don’t have alignment yet.”

💡 This response shifted power back to us.

7. Help them feel victorious

Enterprise deals close when people get something.

💡 Give your legal team minor clauses

💡 Give procurement a concession

💡 Give your champion visible wins

➤ Example: Allowing legal to redline an irrelevant clause sped up a Fortune 500 deal.

8. Be efficient internally

Sales teams can slow deals more than your buyer.

💡 Know who to bring in and when

💡 Escalate things quickly if needed

➤ Example: I brought in my SE the day after a CTO question. Speed builds trust.

9. Always engage timeline

Deals without timelines are going away.

💡 End calls with another scheduled

💡 Build urgency with your champion

➤ Example: On a $600k deal, we co-created Google Sheet timelines. That urgency kept our deal momentum strong.

10. Capitalize momentum

Extended gaps weaken your deals closures.

💡 Follow up quickly after your strong calls

💡 Keep next steps moving within 48 hours

➤ Example: After a demo, I sent recaps and booked the next call within two days.

Free Resource:

Value-based pricing closes bigger deals

Craig Hewitt provides the #1 lesson from closing enterprise deals: sell before anyone can.

You can’t outsource large deals early - workflow mastery remains essential:

1. Avoid startup traps

📌 Most founders chase prospects who talk but don’t buy.

⇒ Example: A founder pitches $50k compliance automation to a 10-person startup. Great feedback, zero chance they buy.

Talk to people with budget and issues your product solves.

2. Strategic prospecting

📌 Begin with your sales hypothesis:

Customer X has problem Y, and we solve it better. 

📌 Apply inbound and outbound techniques.

⇒ Example: A cold email saying, “Hey, I noticed companies your size are seeing CAC double since 2023. What’s been your experience with this trend?” ignites dialogue.

Only target prospects who feel the pain you solve.

3. Discovery > sales pitch

📌 On the first call, don’t demo. Dig into three layers of pain:

• Surface: “How’s your team’s performance doing?”

• Consequence: “What happens if this continues?”

• Personal: “What does this mean for your position?”

⇒ Example: A VP of Sales admits, “If quota misses continue, I could lose my job.”

📌 That’s the kind of urgency you can instantly sell to.

📌 Earn demo rights only after you’ve uncovered pain.

4. Experience-built demos

📌 Demos aren’t feature tours - they’re custom narratives.

📌 Personalize with the customer’s logo, data, and use case.

⇒ Example: A SaaS founder rebuilt their demo with actual prospect data. Conversions jumped from 12% → 47% in 60 days.

Make customers see their future self in your product.

5. Value-based pricing

📌 Low pricing signals low-quality value.

📌 Enterprise buyers distrust cheap tools.

Price to reflect issues solved, not fear of scaring prospects.

⇒ Example: A founder was scared to quote $5k/month and tried quoting $15k instead. Tire-kickers disappeared, deal sizes tripled, and close rates improved.

Pricing isn’t just revenue - it’s buyer qualification.

Contracts are bigger than your products

Jamal Reimer tracked down how sellers build their executives’ approval first.

The best ones didn’t force products— they played roles decision-makers valued.

1. Your personal story

✅ Big deals often hinge on money, not features.

A 7-figure seller halted selling software and began selling the contract instead.

❖ Delayed costs matched fiscal cycles

❖ Guarantees shared downside risks

❖ Flexible scaling tied to outcomes

↳ Example: While competitors ran product demos, he modeled terms, adjusted renewals, and built risk-sharing mechanisms.

Victory wasn’t the product - it was financial alignment.

2. How to play the role

✅ To position yourself in this role, think like a CFO.

❖ Diagnose their financial pain

❖ Speak their money language

❖ Use contracts as differentiators

Sell them financial outcomes, not product features.

3. Where to play the role

✅ Financial creativity achieves what product features can’t.

❖ Incumbent displacement: when tech is equal

❖ CFO-driven deals: when money matters most

❖ Budget buyers: when timing kills great solutions

The Financial Fixer persona always excels in the right settings.

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