By: Cory Bray

In this guest post, Cory Bray talks about how he sees customer training fitting into the Sales Enablement Ecosystem, a framework that he and Hilmon Sorey outlined in their book, The Sales Enablement Playbook.

Most software companies pride themselves on making products that are easy to use. While most modern technologies incorporate a user experience that’s superior to those of past generations, that doesn’t mean anyone can pick up a product with no guidance and be successful.

Here’s a test:

Find a friend who has a different brand of phone. Pick it up, Google something, take a screenshot, then email that screenshot to yourself.

You might pass this test, but odds are, you’ll fail. These are basic functions, and the companies who make these phones have spent BILLIONS on R&D. Has your company even spent a million? However, with a little training, you would be an expert at using your friend’s phone in short order.

I firmly believe user training is critical for the success of sales and customer success teams. As a result, I’m excited to explore how training fits into the Sales Enablement Ecosystem.

Trial Period

If “try before you buy” is part of your sales process, you know there are certain things that must happen for a trial prospect to convert to a customer. Here’s a typical trial process:

  • Champion wants to buy a product
  • Decision Maker approves a trial
  • End-Users get access to the product for a period of time
  • Decision Maker gathers feedback from end-users at the end of the trial

If the last step doesn’t go well, the deal is probably dead. I’ve been a part of over a hundred free trials, and in my experience, untrained users give up quickly and the deal dies. Training users doesn’t guarantee that the deal closes, but it mitigates the risk of an “unforced error.”


Similar to what happens in a trial period, if the end-users at your accounts don’t learn how to use the product, they will likely give up soon after the deal closes.

Sure, the deal already closed, but you want ALL end-users fully trained for several reasons:

  • Upsell or Cross-Sell: If your initial users are not successful, it will be hard for the company to justify spending more money in the future
  • Renewal: Customers churn when end-users don’t engage with your product
  • Advocacy: Farming referrals from your customer’s users, as well as users who move on to new companies is impossible if they didn’t find value in your product

Many companies have teams for both customer success and customer support, though neither are well-positioned to handle 1-1 end-user training; it’s just too high-touch and too expensive. Skilljar bridges this gap to ensure the Success team can focus on driving incremental revenue and the Support team isn’t the front-line solution for basic Q&A.

Internal Customers

How can someone sell a product and expect successful adoption when they don’t know how it works?

Some sales leaders think sales reps should only qualify prospects, negotiate the contract, and close…but it’s not always that simple. A big part of sales is increasing the buyer’s confidence that what they are buying will solve their problem with a limited (or at least known) amount of risk. Sales reps who obviously don’t know the ins and outs of a product tend to destroy buyer confidence.

Most software companies release new features every 2-6 weeks, which can be overwhelming to customer-facing teams. However, I guarantee that your sales reps and customer success managers would rather spend 30 minutes a month brushing up on new releases when the other option is discovering a new feature on a live demo in a prospect or customer’s office.


There are a lot of ways customer training can impact the sales enablement ecosystem within a company. Whether your goal is to close deals, develop new leads, or make your existing customers successful, it’s likely that a greater focus on customer training could be important on your path to success.

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Cory Bray is a Co-Author of The Sales Enablement Playbook and a Co-Founder of ClozeLoop.