Speed-Run Enterprise Deals (But Only the Right Ones)

A customer wants to pay you $30K? Great! Another wants $50K? Even better!

Not if you have a true FDE model!

If you’re running a high-touch sales model - meaning deploying engineers on-site, building custom solutions, providing dedicated support - such deals will kill you.

The math is brutal:

A forward deployed engineer costs $200K+ fully loaded. Add travel, training, and overhead on top.

Meaning each FDE needs multiple six-figure accounts just to break even.

Sub six figure contracts only work if you have strong conviction in significant expansion fast:

• Start small: $30K pilot (enter below procurement threshold)

• Year 1 target: Must see path to 10x ($300K)

• Year 3 target: See path to another 10x ($3M)

No clear path there? Walk away.

Everyone’s adopting the FDE model. Few think about the contract sizes / unit economics needed to support it.

On top, taking on the wrong customers doesn’t just waste resources - it also teaches you the wrong lessons.

True FDE models need large contracts. Small companies can’t provide them. Plus they also have different problems, buying processes, success criteria, etc.

Every hour spent serving them is an hour not spent winning customers with significant expansion opportunities (enterprises)

That said - if you find the right customers, move SCARY fast!

For those, traditional enterprise sales will kill you: Six-month pilots, procurement delays, endless alignment meetings, etc

By the time you close, a faster competitor owns the account already.

Here’s how to compress months into weeks:

Start building before the contract exists!

Yes, you read that right:

• After your first discovery call, immediately build a custom proof-of-concept. No purchase order. Maybe an NDA. While competitors schedule meeting three, you’re showing working software.

• Run legal in parallel, never in sequence. While lawyers debate indemnification clauses, your engineer is already building. By the time the MSA is signed, the customer has seen their problem solved. The contract is a formality, not a gate.

It’s all about showing value as quickly as possible.

Here’s what HappyRobot discovered: There’s zero correlation between paid pilots and closed deals - free pilots convert just as often. Optimize for speed and proof, not pilot revenue.

Instead of negotiating a pilot contract, sign a simple Scope of Work with three things:

1. Start date

2. End date

3. Two review meetings (book them immediately - now everyone’s accountable to a timeline, not a vague intention which makes it far easier to sign than a full contract)

During the pilot, over-communicate:

• Daily standups for high-stakes deployments.

• Weekly check-ins minimum.

• Solve problems in real-time. No surprises at the end.

The customer should feel constant momentum and never wonder what’s happening.

In summary - in the new world of AI-driven outcomes: Be ruthless about selection (qualify hard), then frighteningly fast with execution.

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Enjoyed reading this?

Then check out my conversation on the focal podcast with Pablo Palafox, the Co-founder / CEO of HappyRobot ($60M+ raised from a16z, YC, Base10)

Youtube | Apple Podcast | Spotify

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