Prepare to Win Enterprise Sales [Webinar Recap & Recording]

enterprise sales

One thing Skaled CEO Jake Dunlap is passionate about enterprise sales and the art of executing large-scale, high-value deals. That’s why we were excited to invite Matt Cameron of Saasy Sales Leadership to discuss the best practices and potential shortcomings of modern enterprise selling in a webinar conversation earlier this week. There were a ton of great insights that we’re pleased to share with our most enterprising sellers below! 

Defining Enterprise Sales

What is Enterprise Sales? According to Jake, it is a deal with multiple groups involved in the initial purchase, which is meant to solve an issue that is a current priority for the company, and that has the primary sale of “land and expand.” The organization is complex. It is up to you as a seller to navigate and project manage. The path to grow the account is just as important as getting your foot in the enterprise door.

Matt agreed and added that enterprise sellers have to realize that you are not selling the whole deal upfront. You have to do a proof of concept by departments of the organization. You also have to understand that if you’re doing multi-stage, multi-party, and multi-month sales cycles, you have to make sure it’s not for small-scale deal value.

“Enterprise is about playing chess. It’s playing the patience game,” Jake said. Yet you also have to bring your own momentum to an enterprise deal to ensure its success. It’s also not merely about the tech. But about how you’re going to help your customers’ customer – it’s all based on expertise.

enterprise sales ready


Some Tips and Pitfalls of Enterprise Sale

When selling enterprise deals, Jake and Matt recommended diligence. C-Suite executives are now the post-COVID approvers. You will get delegated during the sales cycle, but enterprise sellers can ask for return access once you’ve shown you’ve solved the issues and proven the concept.

To get into the C-Suite, you need to know something that a CXO needs to know now. Better understand what the corporate goals are, understand how the business works. Discuss risks and reduce them. It will be different for every person, all with personal motivations, so ask how priorities trickle down and not be afraid to find out.

What are some warning signs you’re not getting enterprise sales right? Jake and Matt mentioned a few to be aware of: 

  • The enterprise’s budget for your product or service goes away as non-essential spend 
  • There is no return access to the C-Suite executives 
  • There are no-shows to meetings you set up, or there are unreturned calls and email communications

Ego and pressure also get in the way of not looping in the right people in enterprise sales, such as sales leadership. There are no lone wolves; you don’t need to do it on your own. It’s acceptable to ask for support, but be sure to do so by building rapport with your internal team first so they will help when you need it most.

product ready enterprise sales


Webinar Overview

These were some of the highlights of the range of enterprise sales issues Jake and Matt covered. The core of which were:

  • Getting ready to sell enterprise
  • Getting the C-level meeting
  • Being C-Suite ready
  • Aligning on value and competing to win


You can watch it in full at the beginning of this article. And if you have more in-depth questions on how you can begin selling enterprise-level deals, connect with us on LinkedIn or contact the team directly.

About Skaled


Achieve double and triple client acquisition rates with demand generation and growth hacking.

Get Free Assessment See Resources