The Complete Guide to Enterprise Sales

What is it, why should you care, and how can you begin?

The world of enterprise sales (or “complex sales”) is a good place to be — bigger playing field, bigger impact, bigger revenue, and exciting challenges.

But it can be hard to know where to begin. Ask an enterprise sales rep what they’re selling at the start of the enterprise sales process, and you might hear: “I don’t know yet.”

That’s because enterprise sales is not about selling products. It’s about delivering outcomes. We need to understand where the customer wants to go and work with executives at that company to get there. If this sounds complicated, don’t worry. We’ll break it down.

In this guide, you’ll learn:


What is enterprise sales (also known as “complex sales”)?

Enterprise sales is when you sell to large companies. But any sale can become an enterprise sale when the stakes are high enough, for example, when a product comes with a large business impact, a multiple-year contract, a complicated implementation, or a lot of risk.

Because enterprise deals involve business-critical buying decisions, the customer typically asks multiple companies to submit bids for the contract and brings in decision makers across multiple departments before making a choice.

Why is enterprise sales important?

Many companies and salespeople view enterprise sales as an opportunity to:

Build brand credibility with world-class customers.

Imagine landing a company like Cisco. Apple. Disney. HP. Closing with these companies gives your business a halo of credibility and helps you build momentum.

Kick-start your revenue with just a handful of well-executed deals.

Because the deal sizes are large, enterprise sales can create a solid ground of revenue to stand on. This revenue becomes predictable because it recurs over time, and this revenue only grows as we land and expand, adding to the products already installed on the customer base.

Deepen your relationships for the long haul.

Enterprise deals don’t happen unless we bring real value to our relationships. During the course of the long enterprise sales cycle (often many months), and during the course of a long enterprise deal (often several years), we build lasting, recurring relationships, and that’s meaningful.


What Is Sales Management?


Sales Operations 101


What are the challenges of enterprise sales?

The world of enterprise sales is not without its ups and downs.

The sales cycles are longer.

It can take months or even over a year to close a deal. That’s a lot of time to keep working and to keep the faith. It also leaves a lot of time for things to go wrong, or fall part entirely.

The room is bigger — and reading the room is harder.

We have to be smart about understanding the complexities of organizational behavior, and understanding the key influencers. If we don’t, we can waste a year trying to sell to the wrong people.

The selling motion needs to be airtight.

When we do find the right people, we need to be prepared to speak their language and solve their problems, or they’ll move on to the next thousand people who are trying to sell them something. That’s why we can’t do this alone. It takes a team with all kinds of expertise, working in lockstep, to close an enterprise deal.

How do I create an enterprise sales model?

So you’re ready to take the plunge into enterprise sales? Follow these steps.

Sell the right thing.

Did you remember to build an enterprise-friendly product? There will always be companies with promising products for commercial accounts that go after the enterprise — and fail. Sometimes it comes down to not solving a problem that enterprise customers care about. More often, it comes down to scale. Can the product work for thousands of users? Can it scale to millions of cases a day?

Focus on the sweet spot in your market.

Enterprise sales comes with tough decisions about which accounts you decide to go after — and which accounts you don’t. How can you get more prescriptive, more dedicated, and more intentional? How can you get more proactive?

If you’re an account executive initially going after the enterprise market, and you’ve landed a Fortune 50 company, you simply can’t go manage a hundred other accounts. The enterprise go-to-market model carries a temptation of spreading yourself too thin. To avoid this temptation, put yourself where the highest chances of success are, and forget about everywhere else.

Get into “solutioning.” (And here’s what that actually means.)

In commercial sales, where we’re selling to small and medium businesses, we’re taking our demos and giving them a quick rinse and repeat. But in enterprise sales, we need to do more than swap out logos on a deck. We need to really step into the customer’s shoes and show them that we’re knowledgeable about their business challenges, their competitive space, and their strategy for growth.

Then, as we engage with executives to validate our ideas for how to solve their problems, we earn the right to come back and present those ideas over time. That’s solutioning — and it’s why enterprise sales reps are more like consultants or trusted advisors.


How do I build an enterprise sales team?

How will we prove business value to the chief financial officer? How will we prove ease of implementation and back-office integration to technical leadership? How will we get board approval?

Enterprise customers need a thorough selling motion that brings in different skill sets, from digital advisors to solution architects. Completing the enterprise sales process takes diverse and brilliant thinking all the time — and at scale. Visit Trailhead to learn about the best hiring practices for sales teams.

Enterprise sales team structure


Sales Leader

Directs a sales team and brings together sales channels to plan for growth — and make it happen

Account Executive

Manages existing customer relationships and finds opportunities to build new ones

Digital Advisor

Creates a digital transformation plan that applies the latest technologies to the deal

Solution Architect

Shows how a solution can be implemented in a customer’s IT environment

Customer Success

Improves the customer experience and increases adoption and use of the product

Business Development Representative

Generates new, qualified prospects through cold outreach

The art and science of enterprise sales

Enterprise sales is an art. We paint a vision of the future, and we bring along a transformation roadmap to get there. It’s also a science. We keep the lights on, we run the end-to-end business, and we keep an eye on metrics. Read how dashboards can help you track all the numbers that matter.

Enterprise sales metrics that can measure your team’s success


Run rate

A prediction of upcoming revenue for a longer period of time (usually one year), using current financial data

Win rate

The percentage of opportunities (potential customers) that are closed to become actual customers

Customer retention

The percentage of customers who continue to buy and renew over time, creating recurring revenue

Customer lifetime value

A prediction of how much money a customer is expected to spend on your company over their lifetime

Pipeline velocity

How quickly deals move through your pipeline (the stages of your sales funnel) and generate revenue

Pipe coverage

A ratio that compares the sum of all your sales opportunities with your quota (revenue target)

Hiring an enterprise sales team

We need to hire people who can carry both the art and the science inside their heads at all times. That’s not easy. This principle can help: Hire for character, train for skill.

Here are the traits to look for:

Long-term and short-term balance

Patience and urgency may seem at odds with each other. Not in enterprise sales. If we play the short-term game with a customer and sacrifice long-term value for immediate gains, then we can stumble and never recover because in business — as in life — everyone talks. We have to be willing to play the long game while collecting little wins along the way.

Curiosity and creativity

Enterprise sales is complicated. (We’re not exactly selling shoes.) So we have to constantly learn, go and understand a problem, and build a solution message around it — a story. At the beginning of an enterprise sales deal, we face a big, blank space, and it’s up to us to fill it in. Curiosity and creativity will get us there.


At Salesforce, maybe it seems like it’s easy for us, but we work hard for every dollar. Enterprise sales reps are thinkers and strategists, but we’re also scrappy and eager to put in the work, and that will never change.


What we do takes leadership to bring together the full force of selling, support, and acting as partners to the customer and their journey.


How can I succeed in enterprise sales?

So now you’ve built your team of rockstars, you’re showing enterprises their future, and you’re mapping that vision back to what you want to sell. You’ve got products installed on the customer base, and you’re feeling good.

Think again — because you haven’t reached the mountain top. You’ve reached a plateau. The question is this: How are you going to take things to the next level, where you’re adding products, building customer relationships for life, and growing your business?

Forget about all the things you hear about great leadership, integrity, and values. Yes, fine, but those are table stakes. At the end of the day, the best enterprise sales reps are focused on these three things.


Know your customers.

You can look at datasheets, listen to earnings calls, and read the investor decks, but this kind of knowledge pales in comparison to the knowledge that comes from experiencing the customer’s product for yourself. Go buy adidas shoes if you’re selling to adidas. Go stay at a Marriott if you’re selling to Marriott. Go beyond the facts and the numbers, and discover something the customer didn’t know before, and bring that insight to them.

Know your products.

If we don’t know our products, then we don’t know the area that we’re responsible for. In our explosion of growth at Salesforce, it hasn’t always been a smooth ride. As products multiplied, there were times when we got a little too visionary without being able to back it all up. And that’s when we would hit another plateau. How did we keep breaking through? By bringing it back to basics. What are the products? And what do they do? Visit Trailhead to learn how to give dynamic presentations that stick.


Product expertise became even more important during the pandemic

In May 2020, we asked 3,500 consumers worldwide: “What is the most important quality in a salesperson?” Then in June, we asked them again.
May 2
June 15

Know your stories.

But people don’t buy products. They buy solutions to problems. And we don't sell products. We deliver outcomes. Customers want to know that we’ve done it before. We don’t even buy socks without reading several reviews. Enterprises are the same way. We need to bring them clear examples of what we’ve done with other customers, how we’ve done it, and how things went.

Why do I need enterprise sales software?

Enterprise sales reps can often operate off book. It’s all in our heads. The role of customer relationship management (CRM) software is to capture all that collective wisdom that teams have in their heads, and speed everything up, which is critical for edging out all the other companies clamoring for deals.

Then when we bring in advanced analytics like artificial intelligence to help us focus on the most impactful tasks, we spend less time on waste, and more time on the right stuff.

For example, we can pinpoint the most valuable leads to go after. We can zero in on the tasks that are moving deals forward and set those best practices into motion. We can load up on account and opportunity intelligence, and bring more value to the table. Read how sales teams can set priorities and speed up selling with AI.

So, software is an intelligence multiplier, and that’s critical. Because the person who can bring the most powerful insights to the customer — and show them their future, and guarantee their outcome — is going to win.


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