The enterprise sales cycle: How to win Fortune 500 business

As a Principal Account Executive on the Strategic team at Dialpad, I’ve sold to huge global organizations including RE/MAX, Tuff Shed, and many more Fortune 500 companies.. And I’ve experienced firsthand just how different of a beast the enterprise sales cycle is.

The relationships are more complicated and the sales cycles are longer—but the payoff (literally) is always worth it. In this guide, I’ll walk you through the ins and outs of enterprise sales cycles, and how sales teams can empower their reps to close these deals more consistently and effectively. Let’s dive in.

What is enterprise sales and the enterprise sales cycle?

Enterprise sales refers to the process of selling products or services to large organizations (also known as enterprises). Businesses that sell to other businesses tend to define “enterprise size” differently—some view a company that has over 1,000 employees as an enterprise, while others view companies that have over 10,000 employees as enterprises. These enterprises are typically larger corporations with complex structures, significant budgets(!), and more extensive decision-making processes.

How does the enterprise sales cycle differ from SMB sales?

The enterprise sales cycle is very different from selling to smaller businesses or individual consumers, because of a few main factors.

Longer and more complex sales cycles

The sales process can take several months, sometimes even years to complete. That’s because enterprise deals involve multiple decision-makers, back-and-forth negotiations, and rigorous evaluations of the product or service's fit with the enterprise's specific needs and requirements.

(This is where having a solid sales enablement program can really help your sellers adapt to these complicated sales cycles.)

More relationship-based

Building strong relationships with key stakeholders within the enterprise is crucial. Unlike with SMBs, where you’re often selling directly to the company owner or CEO, enterprise sales reps often need to multithread or work closely with various departments including executive leadership, IT, finance, and operations, to address each of their unique concerns and demonstrate the value of the offering.

More requests for customization and scalability

Enterprises often require customized solutions that can be scaled to meet their specific demands. The ability to tailor your products or services to your enterprise customer's needs and integrate them seamlessly into their existing tech stack or systems is vital.

Typical enterprise sales cycle stages

The enterprise sales cycle involves a fair number of different stages (and often the cycle doesn’t end once you’ve closed a sale). Usually, you can break these down into several key steps:

Prospecting

First, you have to identify potential enterprise customers who could benefit from the product or service that your company offers. If you’re a full-cycle rep, you’re responsible for the entire sales cycle, from beginning to end. In other companies, you’ll have SDRs or BDRs whose responsibility is to handle prospecting.

Either way, LinkedIn Sales Navigator is a must-have tool if you’re in enterprise sales because it gives you a good idea of who you’re selling to. You can look up your prospects’ job titles, how long they’ve been at their current company, see if you have any contacts or interests in common—which all helps when you make that first contact with them.

Dialpad’s voicemail drop feature is also really useful. Believe it or not, cold calling still gets results today, but the one biggest challenge for salespeople is… Leaving voicemails.

Why?

It usually ends up taking 20 to 30 seconds to leave a voicemail, which is effectively the same amount of time it takes to ring someone’s phone a few times. Voicemail drop lets me drop a pre-recorded voicemail message into someone’s inbox with just a click, which basically doubles my productivity for cold calls: