Enterprise Sales Lessons: How I Almost Closed Google, Intuit & Oracle

Enterprise sales can be a treacherous territory if you’re an inexperienced startup founder. Here’s the story of how it made my first startup go belly-up.

From B2C to B2B

It was mid 2007. We were a tiny team—just myself as the founder and one engineer. Our open education Facebook app wasn’t getting any real traction, and it seemed like we were slowly losing momentum.

One day, out of the blue, we got a message from a top-senior executive at Google. She was super excited: “This is EXACTLY what I want to do internally at Google. I want to have engineers around the world teach each other.”

As a tiny startup, we were excited and terrified at the same time, thinking: “Wow, we’ve been struggling for so long to get traction in the end consumer space… maybe the way to grow this business is to go and sell it to the enterprise. And finally, there will be some revenue!”

We set up meetings with Google, and more and more high level executives got involved: they loved our product and vision!

We had our doubts. We were too small. Our product wasn’t ready yet. We didn’t know about enterprise sales. But this opportunity was too sweet, too tempting to resist. So we did it: we decided to go B2B and try the enterprise sales route.

This shit is easy

Since we were already at it, we set up meetings with several huge tech companies through our investors. We hustled hard, we pitched perfectly, the product concept was great, and high-level leadership loved it, not just at Google, but also at Intuit and Oracle. They all agreed to do a pilot.


At that point we were high-fiving ourselves, thinking we’re the smartest people in Silicon Valley. I still remember thinking “everybody says enterprise sales is so hard… this isn’t hard. This shit is easy!”

12 months later…

The Google deal fell flat. Intuit was a dud. Oracle broke our heart.

Each in a different way.

We closed the deal. Was there anything else to do?

The senior director at Google was so excited that she ended up joining our advisory board. Awesomesauce!

So we assumed that since they were paying for the software and the pilot their team would make sure to get maximum benefit from it and turn the pilot into a success.

We assumed they would know how to implement our solution into their organization.

We obviously had no fucking clue about enterprise sales.

What we failed to recognize was that top-management pushed the execution down to a project manager. And that project manager wasn’t excited about it. She had little interest in promoting our platform as an internal tool within Google.

Just because someone important, high up in the hierarchy put it on her plate didn't mean it mattered to her.

She went through the motions just enough to be able to say “we tried, but it wasn’t a good fit.”

You have to sell to ALL the stakeholders

That project manager was not a bad person. We just never made an effort to establish a relationship with her. We never sold her on our vision. We didn’t ask her what we could do to support the pilot.

  • We didn’t provide her with any training materials.
  • We didn't ask her what her objectives were, and how we could help her achieve them
  • We didn’t offer a roadmap for the pilot.
  • We didn't supply any KPIs or internal marketing and promotion material.
  • We didn’t make her understand how this could be an opportunity for her career.

We weren’t aware of other projects she could pursue and other vendors who wanted to get Google’s business. We just failed to manage the whole thing. And it fell apart.

We felt crushed. But we still had Intuit in the pipeline…

They probably know better than us

Intuit had this idea of how to use our platform in a way that we didn’t think would work well. It seemed like a really bad way to use our platform but we thought they probably knew better than us. We were afraid to bring it up.

So we kept our mouths shut and figured they’d come up with a way to make it work and teach us a thing or two.

Their “pilot” ended up being nothing more than a poorly written email to their internal user base with no follow up and follow through. The response they got on their “pilot” was weak, and they just filed the whole thing away.

What mistake did we make here? We hadn’t raised the red flags we saw, didn’t suggest any better alternatives and didn’t manage the process. We didn't take ownership of the entire project.

Organizational churn

But the most painful experience was Oracle. We worked almost nine months on closing the deal. We built relationships with a senior vice president, director and managers on different levels.

We had a huge pilot in mind. We worked out a detailed plan of action, identified metrics to measure success, agreed on a budget. They’d be spending tens of thousands of dollars on the pilot.

After nine months of all the schmoozing and hustling and planning, putting all this work in, and just a few weeks before signing the deal, the senior vice president left Oracle to become CEO at a different company.

He took all the people we built relationships with at Oracle with him. We were left with nothing.

It was soul-crushing. We felt like enterprise sales had chewed us up and spit us out. My partner left. I was totally burned out. We didn’t accomplish anything. All that work and no progress, nothing to show for.

It was a horrible experience. I hope sharing this story and the lessons it contains will prevent someone from going through a similar situation. It’s one of the reasons why I wrote a book on enterprise sales and created the 30 day startup sales success course.

Managing the complex sale

In order to manage a complex sales process with multiple stakeholders involved, you need some kind of tool that simplifies things.

Our CRM with built-in calling and emailing shows you the entire interaction history with a given sales lead.

sales-lead-information enterprise

You can also filter by stakeholder, and activity type. So if you want to see all emails you've exchanged with Bob Myer, Head of Sales at Wayne Enterprises, you can easily do so, just as you can filter all calls you've had with Jane Smith, the VP of Revenue.

sales-lead-interaction-details enterprise sales

With full team transparency, sales reps can get up to speed on the status of any deal without having to rely on another rep to give them a briefing, which can help accelerate the sales conversation and reduces internal friction. You can even filter interactions by rep or use our powerful search features to surface information faster.

Here are some questions that can help you find and fix weak spots in your enterprise sales approach:

  • Who are the key stakeholders involved in this deal?
  • On a scale of 1 to 10, how much does each stakeholder want this deal to happen?
  • Does each stakeholder see an opportunity in their career for this?
  • Is each stakeholder excited and passionate about your solution? Have you sold the vision to each person?
  • What are major objections different stakeholders have?
  • Do you manage the onboarding process and pilot yourself and are actively involved in making them work for your prospect?
  • Do you have clear metrics to determine how the prospect defines “success”?

Finally, I want to leave you with these 7 Essential Rules For Successful Enterprise Sales for Startups.

I hope this will help other founders avoid costly mistakes and excel at enterprise sales.

Table of Contents
Share this article