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The Complete Guide to Enterprise Sales

Sales and Revenue Operations Sales Engagement Sales Management Sales Strategies

Is your sales team ready to enter the big league? 

Enterprise sales are the ultimate goal for many B2B sales teams. They provide tremendous value but come with a unique set of challenges. And just because your team is good enough to sell to small businesses doesn’t mean they can cut it with enterprise buyers. 

The enterprise sales process is long, complicated, and resource-intensive. Understanding it in detail is essential to discover how you can improve it.

Luckily for you, this article breaks it down to help you understand. Read on to discover everything you need about enterprise sales, including the benefits, challenges, and strategies you can use to improve your process today. 

What is enterprise sales?

Enterprise sales is an easy concept to understand but much harder to execute. Also known as complex sales, enterprise sales is simply the process of selling products and services to large corporations. It’s a very common strategy in the B2B space, especially for products like CRMs, cybersecurity tools, and other comprehensive pieces of software. 

There are several qualities that separate enterprise sales from other sales methods. Enterprise deals typically have much longer sales cycles, involve multiple stakeholders and decision-makers, require more investment and effort from your sales team, and result in larger deal sizes. 

Ultimately, it’s a matter of scale. Enterprise clients have thousands of employees and millions of dollars in revenue and can easily commit to six-figure contracts. For that reason, the sales process is longer and more complex. Unlike SMBs, enterprise clients don’t willingly sign off a six-figure contract after just a single product demo. 

How is the enterprise sales process different from self-service or transactional sales?

There are three types of sales models — self-service, transactional, and enterprise — each with a different level of complexity and deal value. 

 The three types of sales

Self-service sales lets users buy products without the help of a sales rep. This is made possible using uniform pricing pages, chatbots, and user documentation. Everything is automated, so there’s no need to speak to a human. Of course, these deals are typically very low value since most people won’t pay much more than a couple of hundred bucks without speaking to someone. But that low value is more than made up for by the speed and volume of the sales process. Hundreds of sales can be made per day. 

Transactional sales are slightly more complex and slightly higher value than self-service sales. They typically take the form of the sale of products or services to individuals or small businesses. These sales are straightforward and happen quickly but are often completed with the help of a sales rep, whether that rep is required to explain the product or help the buyer get started.  

Enterprise or complex sales are a different beast entirely. These deals are far more valuable and complex than transactional and self-service sales. They also take much longer to close and require more effort from your sales reps. 

What makes enterprise selling worth the effort?

Given the level of complexity and the amount of effort required, you could be forgiven for thinking that enterprise selling isn’t worth the effort. But that statement couldn’t be further from the truth. 

There are four major reasons B2B businesses place such a premium on enterprise sales.

What are the benefits of enterprise sales?

Higher revenue is one of the biggest benefits of enterprise sales deals. You are targeting big clients with huge budgets willing to spend much more than SMBs. You’ll need to spend more to acquire enterprise customers, but the lifetime value of these customers could be enormous. These contracts will do wonders for your company’s valuation, too. 

Enterprise sales deals can dramatically increase brand awareness. When you can name a well-known enterprise company as one of your customers, it becomes much easier to attract smaller businesses. 

If you want to win enterprise clients, you have to position your brand as a thought leader. That requires a fair bit of effort on your part, but it will set up your brand for long-term success. Becoming a thought leader will further boost your brand awareness and make it easier to attract enterprise and mid-market clients. 

Enterprise clients don’t devote as much time and money to switching providers every six months. By pursuing an enterprise sales strategy, you’ll build meaningful long-term relationships that can be profitable for years. 

The four stages of enterprise sales management

The enterprise sales process may be complex, but it can still be broken down into four easy-to-understand stages: 

  • Discovery
  • Diagnosis
  • Design
  • Delivery 

The four stages of enterprise sales


Every enterprise sales process must start with an in-depth discovery phase. Assuming they already have a list of enterprise targets, sales reps must spend time researching the company and the people they will be reaching out to.

They also need to make their first discovery calls. 

When speaking to prospects, asking a lot of questions is key. You want to understand their pain points, the previous solutions they’ve tried, their expectations of new solutions, who else is involved in the decision, and their timeline for a decision, among other things.  


Once your reps understand their prospects, they can diagnose their needs. What are their pain points, and how can your product solve them?

If your reps have asked the right questions, they should understand their prospect’s pain points. They’ll need to be able to articulate those pain points and describe how your product can meet those specific needs.

You can’t get away with being generic when selling into enterprises. Rather than discussing the general benefits of your products, you need to key in on the benefits that matter to the prospect. 


Now it’s time for your reps to act as trusted consultants. Having understood their needs and how your product can meet them, reps must tailor a custom solution. This isn’t as easy as selling your product’s benefits, however.

Given the size and complexity of most enterprise solutions, sales reps will often be tasked with customizing the product to meet their needs. That means much more work will be done to set up sales demos. Don’t forget reps will almost certainly need to sell their design to more than one stakeholder.  


If reps have done everything right up until now, delivering the solution should be easy. It may have taken a long time, but all of the efforts will be worth it. Now reps need to hand over to post-sales customer support — a vital function in enterprise sales. 

Win b2b enterprise sales with Gong

There is always room for improvement in how you approach enterprise sales. Whether you’ve been selling into enterprises for years or you’ve just created an enterprise sales process, here are seven ways you can improve.

1. Build a winning sales strategy

The success of enterprise deals hinges on your sales strategy. If you don’t have one, choose a suitable sales methodology for enterprise selling. These include:

  • SPIN Selling – which personalizes the solution through great discovery questions
  • Sandler Selling – which sees the sales rep become a trusted consultant
  • MEDDIC – which stops unqualified buyers in their tracks
  • Challenger Sales – where high-performing teams challenge buyers

If you already have an established sales process, involve multiple sellers throughout the process. 

Team selling has a tremendous impact on win rates

Data shows that the more selling personas are involved, the higher the win rate. In other words, don’t make your reps feel like they are competing against each other. Instead, adopt a team mentality and think about changing commission structures to reflect this. 

2. Know your buyer

While self-service and transactional sales can be a numbers game, enterprise sales is definitely not. You can’t burn through a list of enterprise companies and hope to succeed. 

Instead, reps need to know their target buyers in detail, creating well-researched and in-depth ideal customer profiles and personas.

Sales ICP vs Customer Persona

Why create both? Well, a Sales ICP will help you define what an enterprise client actually looks like for your company. Pay particular attention to their size and revenue to ensure they have the budget for enterprise deals. 

Customer personas are essential for learning more about the specific stakeholders your team will be speaking to. It’s worth investing a lot of time into these since they will apply to multiple companies. Because enterprises have such specific and well-defined job roles, the same roles at the same type of companies will likely face the same challenges.  

3. Become a thought leader

Most enterprise clients aren’t going to be actively looking for a solution when you reach out to them. That makes ongoing education essential to keep your company top of mind and to position your brand as a thought leader in the space. That way, when the enterprise starts looking for a new tool, you are one of the first names on their list.

There’s no shortage of thought leadership-based content you can create, including:

  • Blogs
  • Whitepapers
  • Ebooks
  • Webinars
  • Live events

The key is to keep a tight focus on your industry and product. If you can’t pitch your product at the end of a blog or whitepaper, the topic probably isn’t specific enough.  

4. Use case studies to leverage past success

Given the size and complexity of enterprise deals, buyers need to trust you and your product. There are very few better ways to do so than showcasing your success in the form of a case study.

Each case study should focus on a specific pain point you solved, ideally one that multiple enterprise clients may suffer from. It should also mention the enterprise client by name to further leverage social proof. 

Not only do case studies make fantastic sales enablement tools, but they can also be used in your company’s content marketing efforts to educate prospects before they speak to a sales rep. 

5. Communicate clearly with multiple stakeholders

Enterprise sales are long and involve multiple stakeholders. Our research shows the more people are involved in a deal, the more valuable it is.

Deal value increases when more buyers are involved

As a result, your sales reps need to communicate clearly with everyone, set well-defined expectations, and constantly establish the next steps.

Being able to multi-thread is particularly important. Multi-threading is when reps build relationships with multiple stakeholders in a deal. Mastering this skill won’t just help your reps juggle all of the decision-makers in an enterprise deal; it will make them more likely to close the deal, too. 

The number of people involved on the buyer’s side almost triples in successful deals.

That’s because the number of people involved on the buyer’s side almost triples in successful deals. 

6. Support buyers through the onboarding process

Ongoing support and onboarding are essential for enterprise deals. Buyers have spent a lot of money on your product and expect the best service. 

The faster you can help your customers achieve value with their tool, the quicker they can recoup their investment, and the more satisfied they’ll be with their purchase decision. 

A strong onboarding process will also help reduce churn rates, decrease support costs, and increase net dollar retention. 

7. Use enterprise sales software

Enterprise selling is a game of inches. With high competition, long timelines, and a complex process, your team needs every edge possible to close the deal. That’s where enterprise sales software comes in.

Tools like CRMs, sales analytics, and sales intelligence software give reps an edge over their competitors and streamline what can be an incredibly confusing sales process. 

For example, a tool like Gong Assist can help take the right action every time based on hard, cold data. Rather than simply reminding reps to send an email to a prospect, Gong Assist can draft the email and create a meeting invitation. As a result, your team stays focused on revenue-generating tasks rather than wasting time.

Win More Enterprise Logos with Gong

Enterprise sales is the holy grail for many B2B software companies. Deals can be long, complex, and hard to close, but they are well worth the effort in the end. Teams succeed by constantly improving their enterprise sales process, which is why the right sales software can be worth its weight in gold.

Enterprise sales software can automate tasks, improve forecasting and help your reps make the right decision every time. Sign up for a demo today to learn how Gong’s revenue intelligence platform can supercharge your enterprise sales efforts.

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