10 Sales Prospecting Strategies for Enterprise Companies

Copy blog urlTwitter share logoLinkedin share logoEmail to logo
Article featured image
Author photo: Amy Copadis

Amy Copadis


It’s the dream of every sales rep to pull in that big fish. Enterprise clients drive the biggest sales and they’ll earn your company the most revenue.

Besides, reeling in that big fish will make you a sales hero. But we all know that nailing down an enterprise sale isn’t like any other sale you might have.

You may have plenty of enterprise-sized businesses that would benefit from what you’re offering, but how can you discover whether these big fish will bite?

Enterprise sales prospecting is where it all begins.

Today, we’re going to uncover 10 expert strategies that will help you succeed at enterprise sales prospecting:

  1. Focus on your long-term goal.
  2. Improve your social listening skills.
  3. Build credibility through relationships.
  4. Ask the right questions.
  5. Focus on proven results.
  6. Make your pitch clear and concise.
  7. Research, research, research.
  8. Personalize your CRM to reflect your sales cycle.
  9. Develop your team selling skills.
  10. Be available after the sale.

But first, let’s talk about why your approach to enterprise prospecting must be different from prospecting SMBs.

What makes enterprise sales different?

Generally, there are three major differences when it comes to prospecting large enterprises:

Timing. When you’re selling to SMBs, the sales cycle is significantly shorter than when selling to enterprises. This means that you could spend anywhere between three months to one year to complete an enterprise sale.

Decision-makers. During normal sales prospecting, you typically deal with one decision-maker from the company. In an enterprise setting, however, you’ll likely have to present the deal to multiple decision-makers within the company.

In fact, the Brevet Group found that in a firm with up to 500 employees, an average of seven people will be involved in the buying process.

This makes the process much more complex, as you’ll need to appeal to more than one person who has a definite say in the final decision.

Obstacles. Imagine facing a room full of people who all have a say in whether or not you’ll get the sale. Now, each person has their own set of priorities and their own view of the company’s needs. And it’s your job to make sure they’re all satisfied at the end of the meeting.

Enterprise sales prospecting is complicated because you’re dealing with a large set of obstacles. Budget, authority, and need are generally the most common, but in enterprise sales, each person will have unique views of those obstacles. It’s your job to validate and overcome them.

But do these differences make enterprise sales impossible? Not at all. These 10 powerful strategies will help you win at enterprise sales prospecting.

1. Remember that your goal is long-term.

A long-term goal is a thought-out process that involves checkpoints along the way. When it takes a long time to complete this goal, you can still look back on your progress and avoid getting discouraged.

The same idea applies to enterprise sales prospecting.

You can’t expect to use the same process for enterprise clients as you currently do for small businesses. So, to correctly judge how your sale is going, your team will need to adjust its benchmarks.

To do so, set unique indicators for the enterprise sales cycle. These will act as checkpoints that help you see where you are in a sales cycle that will last several months.

Having these checkpoints in place will also help you see which leads are truly valuable prospects.

Image for post 🚀 your prospecting

🚀 your prospecting

Learn about 5 ways that sales teams can prospect more effectively in this webinar.

2. Improve your social listening skills to get ahead of the game.

How do you find the decision-makers in an enterprise?

Using social media will give you a leg up on your competitors, as it allows you to get special insights into your prospects.

While the specific social media platform will probably depend on your industry, decision-makers tend to use primarily two social networks: LinkedIn and Twitter.

Do some social listening on these networks to accomplish two important tasks:

  1. Find decision-makers.
  2. Discover what they care about.

For example, using LinkedIn’s Sales Navigator, you can perform advanced searches to find decision-makers in large companies:

Then, you can explore their LinkedIn profile a bit. Do your headline and summary match up with what they're interested in? What articles have they liked or commented on? What are they writing about?

Then, move on to Twitter. Find out what moves this person, both in business and in personal life. This helps you develop common ground right from the get-go.

Social listening also helps you to find companies that are primed to buy.

For example, let’s say you find a decision-maker from an enterprise prospect. Then, while sifting through their recent Twitter posts, you find a complaint against their current provider.

All of a sudden, you have a prospect who is on the search for a new provider, making this the perfect time to reach out!

3. Build credibility by building relationships.

Remember all those details you discovered about your prospects above?

In your next conversation with them, be it over the phone, by email, or in person, it’s time to put that information to good use.

Remember, just because you’re speaking to the decision-maker at an enterprise, doesn’t mean you need to put on your robot voice. In fact, it’s a good idea to be friendly and treat that person like just another human being.

But while you’re being friendly, remember not to be a pushover.

To gain their respect, it’s important that you present yourself as a peer. The size of your company doesn’t matter; what matters is the confidence you have in what you’re offering.

As we mentioned above, enterprise-size companies have multiple decision-makers. That’s why your relationship-building shouldn’t be limited to just one person. In the end, you need to work your way into the minds and hearts of all those involved in the buying process.

This network of supporters within the company will be invaluable to you later on, helping to convince stakeholders that your company is the right choice.

4. Ask questions that help align your pitch with their needs.

Each enterprise company has their own unique buying cycle with permissions, approvals, reports, and more. Remember, your company is not the only one that they’re buying from, and they have honed their buying process for maximum efficiency.

That’s why you don’t want to impose your own process on an enterprise prospect. Instead, ask the right kind of questions to help you align to their buying cycle.

For example:

  • Are you considering other solutions?
  • How often does your company face [common industry problem]?
  • If you could overcome this problem, what would that do for your company financially?
  • What concerns you about switching to a new provider?

Once you’ve determined where they are in the buying process, you can adjust your pitch to fit them.

First, you’ll want to validate and address any fears they have.

Then, make your product’s value unique to them. Help them see the specific benefits they’ll receive by using your product or service.

5. Focus on proven results.

Enterprises don’t like risk—they want proven results. What have you accomplished in the past with other similar-sized companies?

If you already have other enterprise clients, you’ll have a good place to start.

But what if you don’t?

Your results are not just based on previous clients. Remember that enterprises gain serious advantages working with a smaller company like you.

Focus on benefits such as faster deployment, access to your top-level execs, and more personalized customer service.

6. Make your pitch clear and concise.

When you get a meeting with key decision-makers, it’s important not to waste their time. These are busy people with a lot on their plates, and you don’t want them sitting there wishing they were somewhere else.

Another reason to keep your pitch short is that your words will likely be repeated to stakeholders and other decision-makers who weren’t at the meeting or on that phone call.

So, make it fast and concise. This will require a good amount of preparation so that you can explain important details without wasting words.

7. Research, research, research.

Above, we talked about doing social listening to find decision-makers.

But that’s not the only research you’ll need to do.

You want to find out everything there is to know about this business’ buying process. Find out how long they’ve been with current providers, and if possible, how long it took them to seal those deals.

You’ll also want to learn more about the concerns of stakeholders in this business. Finding them on social media is a good place to start, but don’t be afraid to ask your contact specifically about the concerns of different key people within the company.

Lastly, make sure that you’re up to date on current industry practices and news. When you become an expert on the industry, you’ll bring even more added value to your prospect.

This is the moment when you become more than just a salesperson: you’re now a trustworthy consultant.

8. Personalize your CRM to reflect enterprise sales cycles.

Your enterprise sales cycles are unique, as we discussed above. So, make sure to create those unique enterprise sales cycles within your CRM:

Record the important checkpoints that you identified above and allow those to guide your journey through the cycle. You could set event-triggered indicators such as a meeting with one particular key decision-maker, a product demo, a test with the engineering team, or something similar.

9. Fully engage your team selling skills.

Don’t expect to bring in a big fish alone. With so much work to do, you should be working synchronously as a team to seal this deal. (To really master this, check out The Guide to Team Selling in the Relationship Era.)

So, go over your pitches together.

Adjust the enterprise sales cycle checkpoints and indicators based on the input of multiple teammates. Have more than one team member connect and develop relationships with the decision-makers in the company, allowing them to help you develop that network of supporters.

By working together, your sales team can draw in that big enterprise sale faster and more efficiently.

10. Be available after the sale.

Your relationship with this client and its individual decision-makers doesn’t end after you make the sale.

To really seal in this deal (and maybe even expand it), make sure that you’re still available to your contacts after the sale has already been completed. Check in to make sure that they’re satisfied with the product and that things are going well.

And, after you’re sure that this client is happy, don’t forget to ask for a referral! (It’ll make your Marketing team happy too.)

It’s time to make your enterprise sales prospecting smoother than ever.

Are you ready to reel in that big fish and become a sales hero?

Following these 10 steps will involve changing your attitude and your sales process. Are these easy changes? Probably not.

But we all know just how worthwhile landing that enterprise sale will be for you and your company.

So, now you have the strategies and tips you need. Take this information and turn it into your next big sale!

Try Copper free

Instant activation, no credit card required. Give Copper a try today.

Ideo graphic
Masterclass graphic
Swell graphic
Bubbles graphic
Try Copper free image

Keep Reading

All posts
Arrow pointing to right
Featured image: Copper CRM product principles … 2023 and beyond

6 min READ

Copper CRM product principles … 2023 and beyond

How and why Copper defined our CRM product principles, and why we think they’ll make a difference for our users.

Featured image: An easy way to track your critical workflows

6 min READ

An easy way to track your critical workflows

Building the right pipeline structure in your client relationship system, for sales or non-sales workflows, can help you better manage key processes. Here's how.

Featured image: How to get more leads and hit your sales quota

3 min READ

How to get more leads and hit your sales quota

Skip the looming dread of missing your sales quota with these expert tips on how to get more leads.

Featured image: Case study: SportsDataIO powers a personalized email marketing strategy with Copper X Mailchimp

2 min READ

Case study: SportsDataIO powers a personalized email marketing strategy with Copper X Mailchimp

Fast-growing sports data provider added our Mailchimp integration to Copper CRM to power up their email marketing with personalized newsletters.