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ATD Blog

Why Enterprise Sales Reps Will Never Be Replaced by AI

Monday, November 18, 2019

Imagine achieving phenomenal sales growth with no salespeople.


Well, Dropbox, the file storage company founded in 2007, grew its revenue to $116 million by 2012. Its sales then rocketed to $1.46 billion by 2018. What’s even more impressive is that for most of its short life, Dropbox achieved this remarkable growth with no salespeople.

Dropbox has historically relied on viral growth, together with a referral marketing model, with more than 90 percent of its revenue generated from self-serve channels. (Click here and here for discussions of Dropbox’s business model.)

It’s easy to understand the appeal of no salespeople. No headaches or expense dealing with hiring, training, managing, and paying sales reps.

So, did Dropbox discover a better (and more profitable) mousetrap? Not really.


As Dropbox moved from consumers and small businesses to targeting larger enterprise customers (that’s where the money is),it found that their first self-service sales strategy wasn’t effective.

Selling to the Enterprise Requires a Skilled Sales Force

Don’t take my word for it. Dropbox stated in their 2018 10-K that its “. . . lack of a significant outbound sales force may limit the potential growth of our business.”


Selling to large corporate buyers requires engaging with multiple stakeholders with different, often conflicting needs. You also may need to add sophisticated features to address significant company needs that are more difficult to explain to buyers. And, of course, the sales cycle gets longer. Only a highly skilled salesforce can manage these challenges.

Pivoting your team from a simple to a complex sale or selling to the enterprise is incredibly challenging. If you need to make this pivot, here are a few factors to consider:

  • Does your team have the right sales DNA? A common mistake that sales leaders make is assuming that the same skill set that was successful for a transactional sale can translate over to selling to the enterprise. A sales rep used to a one- to two-call close sales environment will struggle to navigate through a corporate hierarchy, where in many cases the key decision-makers are not obvious. These types of reps may not have the patience or attention to detail needed to manage complex sales opportunities over a long sales cycle.
  • Is your sales process still relevant? If you are pivoting to a more complex sale, you’ll need to re-engineer your sales process. That means changing how you prospect, engage with buyers, qualify opportunities, identify executive sponsors, and demonstrate the impact of your solution. You’ll also need to support your reps with new sales tools, playbooks, and market insights.
  • Does your team have the right sales skills? In a simple sale, a positive attitude and high activity levels can take you far. Once you’re selling to the enterprise, you need a different set of skills. Are your reps doing adequate pre-call planning and research? Do your reps know how to map accounts to identify numerous decision-makers, influencers, and different types of buyers? Can your reps ask thoughtful discovery questions that help buyers understand how problems affect their business? Can they sell against the competition?

As Dropbox’s experience illustrates, there is no shortcut to selling to the enterprise. Only highly skilled sales reps can navigate through corporate bureaucracies, uncover not-so-obvious needs, and explain complicated value propositions.

About the Author

David Jacoby is a managing partner at the Sales Readiness Group, an industry leading sales training company that helps Fortune 500 companies develop and deliver customized sales and sales management training programs. David is a thought leader in instructional design and the use of innovative technologies to deliver online sales training programs. Previously, he was a principal at Linear Partners, a sales consulting firm focused on providing sales effectiveness and development solutions to emerging growth companies. He writes frequently on the topics of selling skills, sales management, sales coaching and sales training. Follow David on Twitter: @DIjacoby  

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