The Complete Guide to Enterprise Sales

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. You 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 and explain which sales software you'll need.

What you’ll learn:

• What is enterprise sales?
• How does enterprise sales differ from small to medium business (SMB) and mid-market sales?
• Why is enterprise sales important?
• What are the challenges of enterprise sales?
• How do I create an enterprise sales model?
• How do I build an enterprise sales team?
• How can I succeed in enterprise sales?
• Which enterprise sales tools do I need?

Enterprise sales is when you sell to large companies. An enterprise sale could include a product with a large business impact, a multiyear 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 departments before making a choice.

Small to medium business (SMB), mid-market and enterprise sales all aim to solve a customer’s challenges, but the scale of that challenge, the sales cycle, and the number of decision makers will differ. When you sell to SMBs and mid-market companies, you may be meeting with one person, and they have the authority to make decisions. You could close the deal in a couple days or weeks. In enterprise sales, the sales cycle spans across the organization. Each stakeholder will need to weigh in with their own concerns and requirements, and this process could take weeks to quarters.

Let’s say you’re meeting with the owner of a local law firm. They’re looking for copiers that work well with their new cloud-based document management system. You demo your company’s out-of-the-box integration with that system, meeting the customer’s need and budget, and the order could arrive for them a week later.

But if you’re selling those same copiers for the same reason to an international law firm, additional stakeholders are involved in the decision. The firm needs its copiers to handle heavy output by many users. The IT team will have integration requirements with existing systems, an operations team may need to determine the employees needed to install and train on the new devices, and then, procurement may need to issue a request for proposal and solicit multiple bids from competitors. Add all of this up and it will likely take many months to make the sale.

While enterprise sales deals often take longer to close, in part because of the stakeholders involved, it’s a critical source of income — both short-term and long term. 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 could grow if you land and expand, adding to the products already installed on the customer base. And ideally, that healthy dose of revenue could recur with a multiyear deal.
• Deepen your relationships for the long haul.
  During the course of the long enterprise sales cycle (often many months), and during the course of a long enterprise deal (often several years), you build lasting, recurring relationships with your customers. This could lead to upsells and cross-sells, you could lean on them as references or case studies, and you’ve created an advocate for your solution wherever their career takes them.

The world of enterprise sales is not without its ups and downs. With more stakeholders, extensive sales cycles, and longer-term, larger-budget deals on the line, challenges are a natural part of the process.

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 the customer engaged, and it leaves a lot of time for things to go wrong, or fall part entirely. This could also make it harder to predict an accurate sales forecast.

The room is bigger — and reading the room is harder. Enterprise sales often include 10+ stakeholders, and everyone needs to buy in before you can ink the deal. If you don’t, you can waste a year trying to sell to the wrong people. And with a room full of voices, you’ll need to cut through the noise to zero in on your key advocate.

The selling motion needs to be airtight. When you do find the right people, you need to be prepared to speak their language and solve their problems on their timetable, or they’ll move on to the next thousand people who are trying to sell them something. It takes an always-on approach, knowing your product in and out, and working in lockstep with your key team members to make the most of every meeting — all at the drop of a hat.

So you’re ready to take the plunge into enterprise sales? Selling to enterprises calls for a slightly different approach. You’ll need to focus on products that can scale, hone in on your key prospects, and act as an advisor to your customer.

Enterprise businesses are run at scale, so it’s important to make sure that any products you sell to them can be implemented at scale. First, identify products in your portfolio that can be easily and quickly produced without a lot of dependencies, which can slow down delivery. Cloud-based software is a great example — the core platform is the same regardless of customer business size. All you have to do is sell additional licenses.

You can also tailor the idea of scale to what your customer needs. If your buyer balks at how many licenses they might need to scale, you could consider a consumption-based pricing model that scales based on adoption and usage.

There are thousands of enterprise companies, but that doesn’t mean you have to sell to them all. Give yourself the highest chance of success by narrowing the focus to companies that best match your product.

But how can you get more prescriptive, dedicated, and intentional with the companies you pursue? Research and analyze your prospective enterprises and rank them based on how they align with your offering. Any enterprise that doesn’t make the cut should not be part of your enterprise sales activities. A sales automation tool could help to save some rabbit-hole hours deciding the most effective leads to nurture.

When you’re demo-ing to your customers, you need to do more than swap out logos on a deck in enterprise sales. You need to step into the customer’s shoes and show them you’re knowledgeable about their business.

The enterprise sales cycle is longer, so it’s not a one-and-done presentation. You have ongoing conversations where you actively listen to the customer’s needs. You build relationships by showing customers you understand their business challenges, competitive space, and strategy for growth. Then, as you engage with executives to validate your ideas for solving their problems, you 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.

Enterprise sales takes a loyal and dedicated team to close deals. That starts with hiring the right people with the right qualities, onboarding and training your team through sales enablement, and then measuring the success of the team so they can only get stronger.

Take these steps to build your enterprise sales team:

Most enterprise sales teams have three layers. There’s a management level that oversees the overall direction of the team. The sales reps are the feet on the ground constantly interacting with customers, and a support layer does all the things to assist sales like business development and marketing.

The most common enterprise sales roles include:

• 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 tech stack
• 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 job market is saturated with multiple sites and headhunters, all offering to help you find the perfect candidates. Cast a wide net by leaning into your network for potential candidates for your enterprise sales team. Ask your network for candidate referrals and to share job opportunities on social.

Once you have your leading candidates, follow this principle: Hire for character, train for skill. Look for these traits:

• Long-term and short-term balance. Patience and urgency may seem at odds with each other. Not in enterprise sales. If you play the short-term game with a customer and sacrifice long-term value for immediate gains, then you can stumble and never recover because in business — as in life — everyone talks. You 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 you have to constantly learn, understand a problem, and build a solution message around it — a story. At the beginning of an enterprise sales deal, you face a big, blank space, and it’s up to you to fill it in. That’s where you have to proactively dig deeper, whether you’re reading a public company’s financial disclosures to find their key challenges, seeing what your prospect is posting on social, or researching the experience of your customer’s customer.
• Grit. 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. You need grit to pick yourself up after losing a hard-fought opportunity and start cold calling again, or to stand firm on your price after a two-quarter sales cycle.
• Leadership. What you do takes leadership to bring together the full force of selling, support, and acting as partners to the customer and their journey.

An artist doesn’t just pick up a brush and paint a picture. It takes years of training to make a masterpiece. Same goes for enterprise sales. Once you have your enterprise sales team in place, it’s time to focus on the second part of the principle and train for skill.

You’ll tap into the art side of the equation by hiring for the traits above, but when it comes to science, there are no chemistry lessons here. This is where you use sales training and coaching as part of onboarding and for continual development. It’s called sales enablement and the term is just what it sounds like — to enable sales teams to sell more by giving them the right skills for your business, like helping them get the most out of a sales call or mastering the upsell.

Why do enterprise sales metrics matter? They’re proof that our team is delivering value to our customers and revenue to our company. Knowing these numbers gives us a past, present, and future look at where our company has been and is going.

Data can also tie back to your sales enablement efforts. You can use these measurements to recognize high-achieving team members and track areas where they need to adjust. Some sales tools with AI features can automatically surface that room for improvement based on sales metrics as well.

Create an enterprise sales dashboard for a visual representation of sales metrics, and make sure to include these:

• 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)

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. Now, how are you going to take things to the next level?

Great leadership, integrity, and values are all table stakes. At the end of the day, the best enterprise sales reps are focused on these three things.

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. Buy adidas shoes if you’re selling to adidas. 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.

When the complexity of the enterprise sales cycle weighs heavy, bring it back to basics. What are the products? And what do they do? If you can, try using your product as if you were an end user. Talk to your customers and understand their day-to-day using the product. Get your hands on as much feature information as possible, taking advantage of any sales enablement, marketing materials, or other resources your company offers. And we’re not just talking about the best your product has on offer. You need to know the gaps just as well so you can be ready to speak to those.

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

As you juggle all those stakeholder relationships, customer meetings, and the quota you’re trying to hit, that’s too much to keep in your head. Enterprise sales tools can help you keep track of it all. Customer Relationship Management (CRM) software can capture all that sales data and speed everything up, which is critical for edging out all the other companies clamoring for deals. Sales mapping software can visualize all your prospects in one place. You can augment your CRM software with sales engagement platform that keeps those customer relationships buzzing. Then, AI tools help you focus on the most impactful tasks, spending less time on waste and more time on the right stuff.

Your customer calls you before you’ve even had your morning coffee. Your brain is still a bit foggy trying to remember what moves the needle for them. That’s where CRM software comes in. You can do a quick search for your customer and find their wish list of needs. Check on where the client sits in the sales cycle and see what you talked about in your last convo to keep that natural rapport going. Based on how the call went, you can update your sales forecast, and if you’re looking for a speedy quote, a CRM can whip that up. And with this kind of software in the cloud, everyone on the enterprise sales team can point to this sales data as their single source of truth.

The data in CRM software must be actionable to be valuable. A sales engagement tool takes your CRM data and lets you connect with customers on their channel of choice. Whether that’s tapping out a follow-up email based on a template, getting context for your next call, or helping you plan the next way you’ll engage with your customer, a sales engagement platform makes it easier to build relationships throughout the enterprise sales cycle.

If deals closed equaled how many emails a sales team sends in a day, you’d all be sitting pretty. But it’s often the email quality rather than quantity that matters in enterprise sales. A generative AI tool built into CRM software could automate emails that are personalized, data-informed, and that your customer will actually open and read. Or you could use it to recap your sales call with an actionable summary. Predictive AI can also power sales insights and forecasting throughout your sales cycle using your CRM’s data, so more brain power can go back to developing personal relationships rather than visualizing the latest stats.

Sales mapping software keeps territories organized when you have sprawling enterprise companies spread out with offices in multiple locations. You can visualize CRM data on the map interface and overlay nearby competitor activity or identify potential prospects, so that one territory can lead to endless sales opportunities.

Enterprise software sales tools are an intelligence multiplier. You can pinpoint the most valuable leads to go after. You can zero in on the tasks that are moving deals forward and set those best practices into motion. You can load up on account and opportunity intelligence, and bring more value to the table — 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.