Selling to Enterprise (Just Like Selling to SMB… Right?)

In my early years as a leader, I remember one of the first eye-popping conversations I had with an account executive (AE) on my team. You know the kind…

You pause for a few seconds, think hard, wonder if you heard the person correctly, hope you didn’t, and then say, “Wait, walk me through what you just said.”

So, what was the miss, you ask?

We were talking about how to open up an account we had never sold to — one of the world’s largest shipping companies — and she said, “I got hold of their Director of Marketing, and there’s no opportunity right now, so I’m not going to focus on that account for a while.”

Now, if you’re shaking your head and thinking of all the things you would say, whether as a leader or an Enterprise seller, I’m with you. However, if you’re reading that and thinking, “Sounds right to me!” then read on!

Enterprise selling is one of the most challenging sales processes around, and when you factor in that employees are constantly changing jobs, spending an average of 2.5 years in role, and that CEB data shows that 6.8 decision-makers are involved in each deal on average, we all have our work cut out for us.

What was so eye-popping about the above conversation is that, in enterprise, when the Director of Marketing turns us down for the moment, not only is it a great starting point for a relationship, but they are not, in fact, THE Director of Marketing.

That individual is also likely one of dozens, if not hundreds, of people in the organization with that title and, thus, has the power to influence or buy from you.

Here are a few tips to consider as you try to make the leap to sell to the enterprise space, plus tips on how to navigate it once you’re there.

How Do I Get Promoted from SMB/MM to Enterprise?

As a sales leader, one of the key things I look for is a rep who can run a consistent sales process and post consistent numbers.

It’s not about the dozen small deals or one large deal a year (for most industries) the rep closes. It’s more about:

  • How you bring in the slow and steady deals that consistently come in, and
  • What your process is for managing those deals while chasing one or two monumental deals for the year

I define a monumental deal as one that closes for 3–4x your annual ACV.

Consider also that getting your deals to close consistently isn’t the sole indicator of success. My favorite interview question for anyone who has been successful in their sales career is, “Congratulations! HOW did you do it?”

RELATED: Moving From Mid-Market to Enterprise – Product and Market Readiness

Enterprise selling significantly narrows the playing field for you, limiting the number of accounts you can pursue. So having a tight process around how you identify your top accounts, how you systematically open them up, and how you connect internal dots is critical.

Cracking Open a New Account

With enterprise sales, you could be looking at accounts that have tens of thousands of employees, so here are a few tips on how to get cooking:


Explore your CRM immediately for any opportunities that were open in the last 24 months.

  1. Review LinkedIn to see if the main point of contact at the client (the person tagged to the opportunity) is still there.
  2. Reach out to introduce yourself and begin to understand why previous conversations didn’t materialize into a partnership.

Here’s a great #samsales tip for you as well: When you check LinkedIn and find that the opportunity point-of-contact is no longer at the same company, take one extra step to see who on your team owns the account that individual went to. Then do them a favor and give them a heads up that there may be a great connection to explore.

This tip takes extra time but is a great way to build rapport, pay it forward, and build positive team morale.

LinkedIn Sales Navigator

If your company has a corporate enterprise license of LinkedIn Sales Navigator, this will be one of the most substantial additions to your success.

  1. In Navigator, click on “Advanced Search” for leads and start to fill out the parameters for what criteria matter to you in this account. If you’re only looking for Director of Demand Generation and are specifically interested in those residing in a certain state, you can identify those criteria and run a search to populate a custom list of those individuals.
  2. Once you have your list, take advantage of one of its most valuable tools — TeamLink Extend (TLE). TLE gives any company the opportunity to connect all of its employees in a common network on LinkedIn, so you can see if any of the individuals on your target list are connected to co-workers, even if you are not yet connected to that co-worker.

RELATED: Sales Prospecting On LinkedIn Using The X-Ray Technique

Company Org Chart

Understanding the make-up of your book is critical, but understanding the schematic of each company you’re targeting is even more important.

Let me give you a recent example.

Andy recently discovered that his co-worker was connected to me on LinkedIn (thanks to TLE!) and asked if we could be introduced. He was trying to crack LinkedIn for a data intelligence dashboard technology and wanted my help.

My first question to him was, “Okay, tell me what you sell, and tell me who you’ve spoken with and in what lines of business?”

He could answer the first but floundered on the second, saying, “Well, I spoke to a few people in Sales Ops but I don’t know what departments they work in…”

This is a major miss.

It’s not even a miss, it’s a requirement of the enterprise role.

I gave Andy this guidance. First, figure out what lines of business (LoBs) your target has. Next, plug and play the two tips above:

  • What LoBs are the opportunities in, if any?
  • Who do you know that knows your ideal buyer personas in those LoBs?

This will immediately give you a map of where you know people, where you don’t, and how to start connecting the dots.

When One LoB (Door) Closes…

Finally, one of the most critical components to succeeding here is to understand how to take a “no/not right now” and turn it into a positive.

Often, AEs will begin to focus on a target account, get their email campaigns going, and finally get a response from a decision maker (DM) stating, “Thanks your note. This is actually super interesting to us, but I can’t give you attention for the next three months. Could you kindly follow up with me after the first of the year?”

And often, I find that an AE takes that as a sign to leave the account dormant entirely until conversations with this person can be commenced.


Here’s what you should be thinking: You received a reply from someone critical in that LoB, which means now is the time to start to farm other LoBs.

Ideally, you can start to build relationships across the LoBs, generate interest, name drop that you plan on touching base with the initial DM in a few months, and uncover a wealth of connective threads — especially when prospecting to the same titles.

And with this in mind, by the time the first of the year rolls around, you can connect your DM with all the other DMs in other LoBs that you’ve been speaking with and start rolling a far larger, truly Enterprise — monumental, if you will! — deal.

Sam rose from being an individual contributor in sales to running an enterprise sales team. She also created ON24’s mentorship program, and has seen these tactics successfully used over the course of many years and across all industry types and company sizes.

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