You are currently viewing The Enterprise Sales Cycle: How Massive Deals Come Together

The Enterprise Sales Cycle: How Massive Deals Come Together

Businesses come in all shapes, structures, and scales — and the angles and processes used to sell to different companies reflects that variability. SMB sales cycles come with their own challenges, stages, and appropriate strategies, and the same goes for larger enterprises’.

Here, we’re going to explore the latter. We’ll take a closer look at some key elements of the typical enterprise sales cycle, review the basic steps to the process, and get a quick refresher on how to calculate close rate for longer sales cycles.

Let’s jump in.

Typical Enterprise Sales Cycle

The typical enterprise cycle is characterized by some key elements — here are some of the most definitive ones.


Establishing rapport and relationship-building are particularly important when it comes to your typical enterprise sales cycle. The process is more involved and focused than SMB sales — where you might be expected to churn out dozens of demos every week.

With enterprise sales, you lock in on a single business and interact with several stakeholders within it — having conversations that bear significant weight as the deal progresses. You’re in it for the long haul, and you need to consistently get in front of the right people to see it through.

The best way to get there is by positioning yourself as a helpful resource for your prospects. Building relationships through education and communication might be the key factor in successfully conducting an enterprise sales process.

More Stakeholders

It goes without saying, but your average enterprise is considerably larger than a small or medium business. That means they typically have more balls in the air and factors to account for — so they tend to have more decisions to make and, in turn, more decision-makers to make them.

That trend is one of the key factors that separates the enterprise sales cycle from its smaller counterparts — you’re expected to deal with a much wider range of stakeholders than you would when selling to an SMB.

According to Gartner, The typical buying group for a complex B2B solution involves six to 10 decision-makers, and when you’re conducting an enterprise sales process, there’s a good chance you’ll make contact with most — if not all — of them.

Long Sales Cycle

Your typical SMB sales cycle is much quicker than your average enterprise sales cycle. The former can run as short as a week but generally hovers around 60-or-so days. But the latter is usually much more drawn out. Since it involves more stakeholders and red tape, the average sales cycle for an enterprise deal is usually six or more months long.

Large Contract Value

Again, it’s not revolutionary or insightful to point out that enterprises are bigger than small to midsize businesses. That means that enterprises will leverage your solution on a much larger scale than their smaller counterparts, making for more significant, valuable contracts — ones that will routinely run into six or even seven figures.


Enterprise deals are harder to come by and even harder to land. That scarcity — taken with all the previously mentioned factors — makes the enterprise sales cycle higher-stakes than others.

Basic Steps in an Enterprise Sales Cycle

1. Discovery

The enterprise sales cycle typically starts with you getting a sense of a potential customer’s needs and interests through preliminary talks and research. At this stage in the process, you need to ask thoughtful questions to gauge a deal’s viability and expose a prospect’s pain points.

Those can include questions related to elements like organizational missions, broader company goals, previous purchases, timelines, potential roadblocks, relevant decision-makers, legal processes, and how they define success.

With this information in mind, you can start to tailor a pointed, effective sales strategy that your prospect will be receptive to. It also helps you weed out deals that are less likely to pan out. The enterprise sales cycle is particularly long and rigorous, so it’s important to know you’re using your time and effort wisely.

2. Diagnosis

Understanding your prospects’ business in an enterprise sales cycle doesn’t stop with discovery. If you’re going to sustain a productive relationship with prospects throughout the six-plus months of an enterprise sales cycle, you need to know them inside and out.

It’s on you to identify and find ways to remedy their problems — even ones they might not have considered. Research their industry. If you have businesses of similar scale or nature on your books, take a thorough look into how they leverage your product or service.

One way or another, pin down as many of your prospects’ issues — both current and potential — and translate that insight into definitive, addressable pain points. From there, you can start to piece together a solid picture of how they can leverage your product or service to improve their business.

3. Design

Once you know what your prospects are dealing with, you can start to construct a definitive plan for how you can help them figure it out. This stage involves a certain degree of collaboration with your prospects.

The endgame here is to create a solution that suits their needs, specifically. So it falls on both parties to put together a functional, well-tailored plan — to a certain extent.

Obviously, the onus is mostly on you to make this happen, but it can’t come together without open communication. You need to consistently educate your prospect throughout the process, and tease out problems and solutions as it progresses.

This step underscores the importance of relationship-building in the enterprise sales process. Creating a personalized solution requires significant personal investment. If you’ve worked closely with your prospects, up to this point, you should be in a solid position to put together a thoughtful, specific, effective proposal that will suit their pain points.

4. Delivery

This part of the enterprise sales cycle occurs after your proposal has been accepted. You need to make good on that personalized solution you put together. That means constructing and executing a realistic, tailored implementation plan that works for both you and your new customer.

You also need to have a firm idea of how you’re going to gauge your solution’s success — establish the relevant metrics you’ll reference and report to see whether your product or service is working for your new customer.

Once you have all that in place, maintain an active, productive relationship with the customer. Position yourself as a trustworthy, helpful, reliable advisor that they can lean on to get the most out of your solution.

Calculating Enterprise Sales Close Rate for a Long Sales Cycle

Calculating enterprise sales close rate for a long sales cycle is no different than it is for any other sales cycle. You divide the number of closed enterprise sales by the number of attempted ones.

If you’re interested in enterprise sales, you need to have a grip on the material discussed in this article. These kinds of cycles are challenging and stressful by nature.

They represent a long process that requires finesse, patience, people-skills, persistence, and a stomach for potential failure. But if you’re willing and able to demonstrate those qualities, you should be in a good position to conduct one yourself.

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