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Sales - 8 min READ

5 Enterprise Sales Strategies All Reps Should Know

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Author photo: Shabnam Kakar

Shabnam Kakar


Enterprise selling is different than other types of sales (like selling to SMBs)—you're selling to much larger companies and working on landing much more valuable ($$$$) accounts.

For one thing, enterprise sales (a.k.a. “complex sales”) normally take longer than SMB sales cycles (sometimes over a year). They also require more steps (like RFPs, constant back-and-forths, more decision-makers to communicate with, and a lot more meetings)—and you’re running against a line-up of competitors at the same time.

Enterprise sales are worth the extra effort though. Here’s why:

  • Bigger dollar-amount sales
  • You can close fewer deals and still meet your sales quota (one or two enterprise sales = multiple SMB sales)
  • Increase your monthly recurring revenue (MRR)
  • Bragging rights from closing well-known brands (like when websites put those social proof logos on their homepage—that could be you!)

Slack proudly displays just a few of their impressive enterprise accounts right on their homepage.

With bigger sales, though, comes the need for a bigger sales strategy.

Enterprise sales is a broad topic, but what we’re going to focus on primarily in this article are five strategies you can use to sell to enterprises.

Here are the enterprise sales strategies you need to know.

1. Brace yourself for a long sales cycle.

An enterprise sales cycle can last anywhere between 6-18 months.

Enterprise sales take this long because the high price points make them a more delicate decision for prospects—often, multiple people need to sign off on the purchase.

So, if you want to reel in the big fish, you’re going to have to put in the work needed to close them. This means you need to be prepared to put a lot of time, money, and resources into closing these deals.

You’ll also need to put your team selling skills to use (or learn team selling skills—here’s a good place to start). You may need to bring in your sales manager, the product manager, or some other SME onto some of your sales meetings or demos to boost your credibility and reassure the customer they’re getting the best of your team—and the most accurate information possible.

You’re also likely to go on vacation at some point or be away due to sickness or other reasons. In that case, make sure the other reps on your team are aware of what’s going on with your prospects. All of your interactions with them should be recorded in your CRM, so anyone on your team can easily pick up where you left off, providing a seamless customer experience.

An effective CRM will house all your interactions made with a customer in one place so that no matter who’s working the file, the customer experience won’t be negatively impacted.
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2. Find and build relationships with multiple decision-makers.

If you're used to selling on a smaller scale, you've probably just needed to convince one decision-maker before moving your opportunity to the close phase of the sales cycle. With enterprises, however, there are usually multiple stakeholders and decision-makers involved, and you'll need to get them all on board before you can close a deal.

This means you’ll need to connect with all of these stakeholders and decision-makers early on in the sales process and simultaneously manage relationships with all of them. Oh, and another thing: these people are likely going to be from different departments and have different goals and evaluation criteria from one another, so you can't get away with merely including them all in the same generic emails.

Did we mention enterprise sales are a bit of work?

To find your decision-makers, follow these steps:

Step 1: Make a list of departments that will be impacted by your product. For example, if you’re selling helpdesk software, your list of departments might include:

  • Customer Success (they respond to customer emails)
  • Sales (they’ll need to be able to submit tickets to the CS team)
  • Marketing (will want access to social media comments and website reviews)
  • IT (they’ll be the ones implementing it and need to make sure it’s compatible with the company’s existing tech stack)

Step 2: Once you’ve got your list of departments down, find the managers or directors of each of them and reach out. You can use LinkedIn for this or the company's website, as many organizations have a page on their site listing their stakeholders.

Like many other companies, Adobe has a page on their website dedicated to listing their executive team members and their roles.

You could reach out to them separately, or reach out to one (maybe the one your product would most directly impact; in the example above, that would be CS) and invite them to hop on a call with you and ask them to invite the rest of the crew as well. One benefit of the latter is, if you missed anyone, they'd include them for you.

Remember: all of these people will be using your product a little differently, so their needs and how they're going to evaluate your product are going to differ as well. Make sure you have something prepared for everyone in your initial sales call.

3. Make the decision-making process as easy as possible by providing tons of valuable content and real-life use cases.

Put yourself in your prospect’s shoes; to say they’ve got a lot on their plate would be an understatement.

Now, on top of that, they need to put in hours of research on your product to decide if it’s right for them before they can sign their name on the big cheque. This isn’t always an exec’s number one priority (which is another reason for the long sales cycle we mentioned).

The best way to make sure they don’t put your product on the backburner is by making the overall decision-making process a little easier.

To do this, you need to make the value of your product crystal clear right out of the gate. This goes back to our enterprise sales second strategy—make sure you have a killer pitch prepared well before you jump on to that initial sales call with all the decision-makers.

After the call, back up your product with valuable content like:

- case studies,

- customer reviews, and

- demo videos that stakeholders can easily skim over versus having to scour the web for.

4. Customize your solution to the prospect in your demos.

Most enterprise-level software is customizable to meet a company’s unique wants and needs. For example, every website’s Help Center that’s built with Zendesk doesn't look identical—they're customized to that website's design and align with its branding.

This ability to customize a solution to your prospect’s unique needs should be demonstrated in your demos. Don’t just show them what your product can do; show them what it can do for them.

Putting yourself back in the prospect’s shoes: you wouldn’t invest thousands of dollars in a luxury vehicle without taking it for a spin, right? (Oh, and here are other common mistakes to avoid when running a demo.)

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Learn how to run a sales demo that sells in this free webinar.

So, let them take your product for a spin. Of course, there’s the free trial/demo option, but that gives the prospect a generic, uncustomized version of your product to play with. This may be fine for smaller customers, but if you’re trying to close an enterprise deal, you’ll want to put in more of an effort.

Instead, what you can do is create detailed mock-ups showing exactly how your product will look once it's integrated with their existing tech stack.

Will this take time and cost your company money? Absolutely.

But this also may be what stands in the way of closing a deal, and—considering the amount of revenue on the line if you close it—the investment in creating mockups is well worth it.

5. Address training concerns.

Making the decision to buy your solution is just half the battle for enterprises. The second half is onboarding their massive teams onto the new product.

Some questions that will be going through decision-makers' heads:

  • How easy is this product to pick up?
  • Who’s going to train the team?
  • How long is training going to take?
  • Can we afford the amount of time we're going to have to dedicate to training?

Our advice? Use these concerns as opportunities to make your sales pitch that much more convincing.

Here are some things sales reps can do to address these concerns:

Offer to provide in-person training.

Talk to your manager and see if there’s any way you can provide training for their team. Not only will this be one less thing for the prospect to worry about, it’ll also give you major customer service brownie points. (Tip: If you can’t provide in-person training, offer to set up live-video training.)

Create training videos.

If your team doesn’t have the bandwidth to provide training with every enterprise sale, invest time and energy into putting together a series of training videos which you can forward to your customers once they’ve decided to buy your solution.

Provide free, ongoing customer support.

This is a huge one, and in many cases, an evaluation criterion that enterprises look at when making a purchase decision. They don't want to deal with a company that's going to take their money and send them off on their merry way; they want a company that's going to continue caring about their success even after the cheque's been signed. (Here's our Customer Success team does it.) And you should want this too, considering how easily they could decide to cancel your product if it doesn't work for them.)

An enterprise sale is a big deal (literally).

Whether you're an established company with a whole lot of SMBs under your belt and want to lock down more enterprise accounts, or a brand-new startup with little to no big clients, just one or two enterprise sales can give your total revenue a massive boost.

Don’t let the amount of time and effort required to close one of these deals scare you. The payoff will be well worth it.

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