How To Be Successful With Enterprise Sales

How To Be Successful With Enterprise Sales

This is is part of my live-learning series! I will be updating this post as I continue through my journey. I apologize for any grammatical errors or incoherent thoughts. This is a practice to help me share things that are valuable without falling apart from the pressure of perfection. 

This is part of my journey to make $1 million in revenue in 2021.

Some Resources:

The Ultimate Enterprise Sales Guide: How Startups Can Close Bigger Deals | Propeller CRM Blog
The Basics of Enterprise Sales | Lucidchart Blog
Sell to Large and Enterprise Businesses Using This 16 Point Checklist
5 Steps To Closing That Enterprise Sales Deal
The Enterprise Sales Process I’ve Used to Close $100,000,000+ | OpenView
What is Enterprise Sales and Why is it Important for Your Business?
The 7 essential rules for successful enterprise sales for startups!
5 Step Enterprise Sales Process: Learn How to Navigate Mammoth Deals Like a Pro – Dan Martell
The 17-minute Guide to Enterprise Software Sales
9 Techniques for a Successful Enterprise Sales Process | CloserIQ Blog

Why Bother?

Enterprises represent an opportunity for bigger sales, more valuable accounts, and a steady stream of income from consistent purchases. This means you can close fewer deals and still meet your quota.


You need to connect with key decision-makers.

Every organization is unique but there is one. This could be the CEO or president but it could also be multiple decision-makers or require board approval. 

Create case studies to demonstrate value. 

What case studies can we use currently? The DMZ is a good one. We have an upcoming one soon. Here is our full list of case studies

I’m thinking that we have the ability to create our deep search media libraries which would help companies find information much more quickly and efficiently. does an incredible job at that with their Case Studies. I need to learn from that.

Lengthy Sales Cycle

Enterprise sales move slower. More people need to sign off. It could take 6 to 18 months!

It could have higher customer acquisition costs and may require multiple demos and customization.

Don’t underprice your service

Are we doing that already? We have pricing on our Speak site. That may make it seem cheap and unworthy. 

Pitching to Enterprise too soon

We may not even be ready for this. There are still a lot of things to get in order. 

Complex sales vs transactional sales

Transactional is what we’ve originally been looking for. Short sales cycle, low-risk. Relatively low touchpoints. Could be under 60 days.

An enterprise or a complex sale is high-risk, has many stakeholders, could take over 6 months, and has a high investment. 

The stages of an enterprise sale:


Discovery is the preliminary stage where the sales rep researches the prospect’s business, talks to them about their needs and requirements, validates the business case, and customizes it to the client.


Research to generate a personalized solution. 


Consult with clients to generate possible solutions you can provide. Likely to be complex and custom. 


The final stage of an enterprise sale is the implementation. Once the company has accepted the proposal, you deliver the solution and track the success.

What are Enterprise Companies?

There are approximately 6,064,000 businesses (firms with payroll) in the U.S. according to the United States Census Bureau, and of that only 0.32% qualify as large or enterprise-sized businesses. Here are estimates derived from that data:

Enterprise Company Table

Sell a Solution 

Not a tool. Not a product. You sell a solution to a problem. What are the problems I am trying to solve?

  1. Too much information to manage
  2. Audio and video becoming more and more prevalent which are even harder to manage
  3. It is hard to find and retrieve information quickly
  4. It is hard to improve people and team’s self-awareness, well-being and productivity

Ways to sell to enterprise

  1. Email campaigns
  2. Write for industry publications and press
  3. Cold calls and emails
  4. Publish white papers
  5. Advertise on LinkedIn
  6. Hire Sales Reps
  7. Prepare requests for proposals

SMB vs. Enterprise

For SMBs, it is much easier to get to a solution that the team can figure out themselves. 

SMB is an abbreviation for small and medium-sized business, sometimes seen as small and midsized business. A business with 100 or fewer employees is generally considered small, while one with 100-999 employees is considered to be medium-sized.

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