The Hidden Complexity of Enterprise Sales

Everyone thinks sales is learnable. And it is. But that doesn't make it easy. Especially closing larger deals.

I chatted to Alexa Grabell, co-founder of Pocus about this. She thought she knew sales. She'd been in sales operations. She'd watched deals close. She understood pipelines, quotas, commission structures, etc.

Then she tried to close her first $100K+ contract.

"I messed up every part of the journey. Multiple stakeholders didn't know we existed. Procurement processes that made no sense. Politics and budgets and timing issues that had nothing to do with our product's value. etc.”

Pocus closed that deal ultimately - through sheer force of will.

Once she hired an experienced sales person, she understood what sales excellence actually is. The lessons were humbling:

• Stop talking so much.

• Ask more and better better questions.

• Map the organization.

• Understand the buying process.

• Build trust before pitching product.

• Create urgency without being pushy.

• Navigate politics without taking sides.

• And much more.

Here's what especially technical founders get wrong about enterprise sales:

• The demo is the least important part: Enterprise buyers don't care about your features. Only about their problems, their politics, and their promotions. The demo is the dessert, not the main course.

• You're not selling to a committee, not a person: Champions can’t buy alone. Legal reviews contracts. Security audits SOC2. Finance approves budgets. IT verifies integrations. Etc. One "no" kills your deal.

• Procurement exists to destroy value: Their job is to pay you less, demand more, and extend timelines. They don't care about your burn rate or runway. Navigating procurement is like learning a new language - e.g. "we'll get back to you" means "we're shopping for alternatives."

• Your sales process is part of your product for enterprise buyers: Organizations judge vendors by how they sell. Sloppy follow-up, unclear next steps, or poor stakeholder management signal future pain. They're buying a relationship, not just software.

• "Interested" means nothing without timelines: Real buyers have urgency. They talk timelines. They introduce you to other stakeholders. They work with you to build a business case. Everyone else is wasting your time.

Enterprise sales is completely orthogonal to building great products. It’s as much emotions as it is logic. Which is why especially technical founders struggle with it.

Respect sales as a discipline as complex as engineering. Learn it. Study it. And hire experienced sellers who can teach you once you’re far along enough.

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Enjoyed reading this?

Then check out my conversation on the focal podcast with Alexa Grabell, Co-founder and CEO of Pocus ($23M raised from First Round, Coatue, Pear, Box Group, GTM Fund).

Youtube | Apple Podcast | Spotify

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