Complete Guide to Enterprise Sales for Tech Companies in 2019


As enterprises move to the cloud and look to optimize their dated processes, the floodgates have opened for enterprise sales teams.

But that’s created a crazy land-grab of companies jumping over each other to gain enterprise attention – which means sales teams now need to tailor their outreach for companies that have big needs, big teams and a lot of moving parts that have to work cohesively toward organizational success.

However, as is the case with any rapid industrial change, there are a lot of questions about the unique nature of enterprise sales, including the sales process and execution of enterprise playbooks. How does a salesperson or team transition into serving enterprises? What factors need to be taken into consideration in order to sell to a large organization that may be undergoing profound digital transformation?

How can you ensure their satisfaction long-term?

These questions are important to answer, especially as more people get into the enterprise sales game. For that reason, we’ve put together this enterprise sales guide to help you understand what enterprise technology sales is, the roles within an enterprise sales team and the enterprise sales process, including pitfalls to avoid.

Understanding technology enterprise sales

Wait… What Is Enterprise Sales?

While it may be true that you’re in the business of selling technology, you may not necessarily understand the full breadth of what you’re doing. It’s possible that you simply think of yourself as a salesperson. But enterprise sales is not just about selling solutions – it’s about building relationships. Being sensitive to these nuances can better tee you up for success.

Enterprise sales professionals have a host of concerns that salespeople who work on a smaller scale don’t. Typically, they must have not only personnel-based knowledge about the decision-makers they’re dealing with, but also a granular understanding of their prospect’s issues as well as their own company’s solutions. For this reason, enterprise sales is also sometimes referred to as “complex sales.”

What Enterprise Sales Isn’t

Enterprise sales isn’t something you can just flip a switch and turn on. There are nuances to developing an enterprise sales process, and your product must be enterprise-ready with typical features and integrations.

Before you decide to jump headfirst into enterprise sales or even invest further in your enterprise sales process, make sure your product and teams are enterprise ready.

Is Enterprise Sales Right for Every Business?

Not every business or salesperson is set up for enterprise sales. You might find that some businesses don’t actually have the problem your product solves, or that it’s easier to take a bottom-up approach when it comes to your enterprise software sales. If that’s the case, you may want to look into sales processes other than the one we’re focusing on here.

In this piece, we’re focusing on “traditional,” complex enterprise sales, which involves a lengthy sales process built on relationships, research and deep organizational understanding.

Enterprise software sales starts with your product

If you’re an established company looking to swim upstream and capture enterprise dollars, it’s not as easy as the boss saying she wants to make enterprise sales a priority this quarter.

Before you set out to make enterprise sales, you need to ensure that your product is enterprise ready.

Ask yourself: does your product have enterprise features? If it doesn’t, then you may want to spend some time retooling before you embark on your new sales journey. Some useful features to consider include:

  • Security controls and authentication: The ability to do single sign-on and enable/disable user profiles from a central location.

  • Role-based controls: The ability to group users based on permissions.

  • Software integrations: Can you work with typical enterprise technology stacks?

  • Product sturdiness: Does your product have the scalability to have hundreds or thousands of users on it simultaneously?

  • Post-implementation analytics: Enterprise leaders are going to want to see how the product is being adopted and used by their teams.

  • Sandbox functions: The ability to perform QA testing in a nonproduction environment.

While these are the typical enterprise asks, you’ll also need to be prepared for custom asks. These may include new product features or the addition of a service and customer success aspect to your business to ensure that the implementation of your product leads to a positive outcome.

If you find yourself under pressure from the board or executive leadership to execute enterprise sales, make sure your product is actually ready for it. This is essential because without these features, you may find your enterprise sales efforts falling flat.

The good news?

Enterprise sales cycles tend to last a very long time. This means you have some time to get your product in order before takeoff. That said, you don’t want to delay too long in getting the sales process underway, and you definitely don’t want to promise an enterprise solution that doesn’t actually exist. Find balance, know your product and be sure that it can actually help your prospects by the time the deal is closed, if not much sooner.

The roles & skills of an enterprise sales team

When it comes to hands-on personnel, the differences between small to midsize software sales and enterprise sales become more apparent. Typically, smaller software sales is a highly automated process. In fact, customers might be able to access the product simply by putting in their credit card and making a purchase, never so much as saying “hi” to another human being.

Enterprise sales is decidedly more complex. Despite a variety of tools designed to make the process easier, human intervention is still needed to make the sale and success of the product in an enterprise setting a reality.

Generally, that means you’ll need an enterprise sales team with a variety of professionals who serve specific functions to keep things moving along gracefully. Here’s the typical makeup of an enterprise sales team:

  • Domain expert: This person is a subject matter expert who is an authority in a particular area or topic. He or she can help identify problems or needs in an organization and define use cases for the software you’re selling.

  • Solutions/sales engineer: This person helps prospects understand and compare the variety of solutions available to them (pre-closure) and troubleshoot issues that come up following the implementation.

  • Post-sales account management: Is your solution continuing to satisfy the customer? Are there new features that your client can take advantage of? Is there an opportunity to upsell? The post-sales account manager answers these questions and keeps customers happy and engaged.

  • Sales operations: Sales operations personnel help define the processes of a sales organization, conduct audits and drive teams toward long-term success. Ideally, this person can monitor sales data and customer relationships to continually improve the sales process.

  • Customer success: This person represents a company as a primary point of contact, helping clients navigate concerns pertaining to billing, product, information and broader support. The customer success representative contributes meaningfully to customer satisfaction by lending a helping hand and is critical to customer retention.

In addition to the people described above, you’ll likely continue to need tradition sales roles like account executives and sales representatives. As you explore enterprise sales, your top-performing sales representatives and managers will probably lead the charge to transform your sales process. Why? Because they’ve built up confidence in selling your product and understand typical buyer questions.

A Note on Enterprise Sales Teams & Skills

Just as enterprise sales teams are generally composed differently from regular sales teams, so too are the skill sets they carry. They may have many skills in common with the average sales operation, but their most indispensable skills include:

  • Building and maintaining relationships with a variety of personnel at large organizations

  • Negotiating things like services and price and overcoming objections within reason

  • Being persistent, particularly in the face of seeming indifference

  • Gathering account knowledge, including the important whos, whats, wheres, whys and hows

  • Having patience and understanding that the enterprise sales process can be very lengthy


Beyond these basic skills, having access to an enterprise marketing team will help bolster the enterprise sales teams with the content and creative they need to be successful. You’ll find that in enterprise sales, you’ll need a lot of custom content, and you should lean on both the sales team and other teams to create these custom content pieces.

Speaking of marketing, it’s time we talk about the importance of marketing and sales alignment in the enterprise marketing setting.

How Do Sales & Marketing Work Together When Targeting Enterprises?

It’s Marketing’s job to develop tailored marketing assets that help guide prospects through the buyer’s journey. They help provide information and persuasive assets that contribute to closing a sale. These assets might be:

  • Custom sales decks made to address specific prospect problems

  • Personalized one-pagers with information targeted specifically to a prospect

  • Playbooks or marketing campaigns designed and launched with specific clients in mind

  • Precisely targeted branded events meant to persuade and wow prospects

These are just some of the possibilities, but needs will vary from organization to organization and prospect to prospect. The best way to ensure that Marketing and Sales are on the same page and giving one another what they need is to build a cooperative relationship between the business segments by having check-in meetings. When it comes to enterprise sales, silos are a no-go.

The enterprise software sales process

Just as personnel, skills, marketing’s role and a plethora of other things differ in the enterprise setting, so does the sales process in general. This is why it’s crucial to understand the unique approach enterprises take to identifying and solving pain points – and why it might be a good idea to document how you engage them.

Often, what happens is that someone realizes there is a pain point at a company and brings it to the attention of someone else, hoping for a solution. Ideally, the problem is communicated to someone in a position to make corrective change.

From there, the decision-maker begins the search for a solution, conducting research and preparing procurement questions in order to find the best possible investment for the organization. Then, contacts are made, and over the course of what is often several months (think 6-8, realistically), decision-makers and salespeople work together to determine fit, negotiate price and, hopefully, close the deal.

That means inbounds from enterprises critically require tailored responses. Beyond that, your company logo needs to appear where enterprise leaders typically search first, like on analyst reports, and you’ll need to build clout among enterprise peers for word-of-mouth recommendations.

Using This Approach to Your Advantage

Knowing all of this about the enterprise decision-making process can work in your favor, particularly if you take the popular and time-tested “SPANCO” approach to getting in front of your prospects.

SPANCO isn’t just a funky word. It’s an acronym for “Suspect, Prospect, Approach, Negotiate, Close and Order.” Each of these words describes a point in the sales journey that can help you guide your potential customers from their post-pain-point discovery and research phase to a closed deal.

To get more in-depth, the process goes something like this:

  • Suspect: An organization is putting feelers out. You may have learned this by monitoring search intent, collecting business intelligence using a platform like Intricately or through word of mouth or social listening. In any case, you have a feeling there’s a problem at an organization that you can solve...

  • Prospect: ...and thus begins your prospecting process. You start sizing your potential customer up, getting a feel for their needs and determining what will best contribute to a successful business encounter with them. You might even start talking to Marketing at this early stage to develop materials that will help you ace this engagement.

  • Approach: With your marketing and sales assets aligned, your research in your back pocket and your pitch prepared, you reach out through whatever channel is most appropriate. Ideally, a conversation is started, even if you have to make contact a couple of times.

  • Negotiate: After you and your prospect work through your sales and marketing assets, determine fit and move closer to the closure stage, it’s time to negotiate. What services will you be offering? What price is going to work for both of you? How long should your contract last?

  • Close: The die is cast. The contract is signed. The negotiations are closed and all parties are satisfied within reason.

  • Order: Time for delivery. Get the assets into your customer’s hands, set them up with the appropriate customer success personnel and, ideally, build a relationship that brings positive returns for years to come.


If that all sounds overly simplistic, it’s probably because it is. In reality, navigating the sales process and getting to a closed deal means really getting into the weeds, anticipating potential issues and dealing with unexpected developments as they come up.

Not every deal will work out in the simplest fashion, but as long as you keep the SPANCO process in mind, you should at least know where you stand at all times. That knowledge alone can give you powerful insight about how to proceed with any given enterprise account.

Measuring your enterprise sales success

We all know closing an enterprise deal takes forever…so what KPIs can you actually measure both during and after the process that will make your next deal just a bit shorter and a whole lot smarter?

3 Sales KPIs for Enterprise Sales to Consider

  • Account penetration: Do you know the ratio of your sales to a customer versus their spend on other solutions? If not, you’ll want to do some business intelligence research to find out. This can help you understand how you’re doing compared to the competition.

  • Deal size: This is the average number of dollars made per closed deal or contract. This is definitely an important metric to keep your eye on. Why? Eventually, it can tell you whether or not certain clients are going to bring about a good return on investment over time.

  • Sales velocity: How quickly are deals moving through your sales pipeline? How much of that time (which is notoriously worth quite a lot of money) is being burned on stalled deals? Follow this oft-overlooked metric closely to understand the health and efficiency of your sales process, then improve that process as needed.

Carefully monitoring each these metrics can give you meaningful insight into a process that can otherwise seem (at times) endless and confusing. The more clarity you have as you navigate the sales process, the more secure you can feel in knowing you’re making smart business decisions.

Pitfalls to avoid in enterprise software sales

Enterprises are needy – why sugarcoat it? Like your own organization, they have a lot of demands and concerns to address, especially as they move into the cloud.

That means your sales, marketing and customer success teams need to be prepared to handle a large organization with complex, sometimes even conflicting, needs as they come in. It also means you need to be aware of any red flags or potential disasters along the customer journey (and after the sale is made).

Some red flags and pitfalls to keep in mind:

  • Death by customization: Creating custom solutions for an enterprise client is almost expected, but you shouldn’t be a yes-man. Make sure the ROI versus the time and effort makes sense.
  • Not asking enough questions: Enterprise customers will be disappointed when they onboard to a product that isn’t enterprise ready. Nip that possibility in the bud with a great discovery process. Ask plenty of questions during the sales process and use the answers to prepare your product and meet your prospect’s expectations.

  • Overpromising and under-delivering: We alluded to this earlier. There’s almost nothing enterprise clients hate more than a software solution that talks a big game that it can’t back up. If, somehow, you make it to a closed deal and a signed contract and they discover you’re not all you said you were, get ready for a blown deal. You can get them to sign the contract, but chances are they’ll ask for their money back when you can’t deliver what you promised.

Surely, there are other matters to keep in mind as you navigate the enterprise sales process. As long as you’re mindful, you shouldn’t have to worry about any of them sinking you. Be attentive during every step of engagement and focus on smart, well-thought-out product delivery.

Setting yourself up for enterprise software sales success

Now that you know the ins and outs of enterprise sales, it’s time to start laying the groundwork for an enterprise sales operation of your own. Make sure you’re thinking about what you want to achieve and that you’re focused on being prepared every step of the way.

Only when you align goals, sales, performance, research, personnel and management can enterprise marketing success be achievable. Since you’re reading this guide, you’re off to a good start…so now, instead of theorizing, why not start executing?


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