From Sales “Trainers” to Sales “Enablement”: Why Sales Enablement Matters, and What’s Required to Sustain.

By Todd Caponi

I recently read an article from 2017 listing the top-ranked sales books of all time. Being a nerd for sales philosophy and its associated books, something jumped off the list to me – which drove me to dig deeper. Next to each of the top twenty, I wrote down the year each book was published. My intuition was correct, making me realize why the sales enablement profession has gone from “sales trainer” roles within companies just ten-to-fifteen years ago to this new world of sales enablement – consisting of departments, societies, communities, and a whole vertical of supporting technology.

Five of the books from the top twenty were published between the years of 1982-1985. It just so happens that this period of time was approximately ten years after the dawn of the Information Age, which is said to have begun in the early 1970s. For those ten years (1972-1982), buyers began to have multiple channels to access information, and suddenly sales professionals found that they were no longer adding value the way they used to. Methodologies, books and entire training companies were founded to address this challenge, primarily taking different forms of “solution” selling.

But what about the other fifteen books on out of the top twenty on the list? Turns out that ALL FIFTEEN were published in the last ten years – roughly ten years after the beginning of the Digital Age (said to have begun in the mid 1990s).

Weird, eh? Well, not really.

As the pace of information proliferation accelerates, so do the demands on organizations to ensure their sales teams are as productive, efficient and competitive as possible.

For salespeople, the depth and breadth of information aiding buyers in their quest on their purchase journey are accelerating at an incredible clip. It spiked in the 1970s and 80’s, then settled down until the expansion of the Internet. Now, the digital age is driving such an explosion of information, how sales professionals add value is changing so frequently that keeping up on their own is no longer possible. Thus, tons of books are shaping the new era of sales philosophies, along with the rapid growth of the sales enablement function.

But now there’s another problem: The speed by which new philosophies, techniques, and methodologies are coming out is almost impossible for sales enablement leaders to keep up with on their own. And if those leaders can’t keep up and their competitors can, the results will show it.

Now, to succeed, sales enablers need communities.

Just seven years ago, I was tasked with building the sales enablement function from the ground up for ExactTarget (since acquired by Salesforce for $2.8B) – and felt like a pioneer at the time. While I networked with other sales enablement leaders from across the industry, we were all just “figuring it out” at the time. Today, that’s much different. Sales enablement has proliferated it’s way into just about every tech company past a Series A stage that I know. And, as the old saying goes, “None of us is as smart as all of us.” Sales enablement practitioners need each other – to learn from, to share best practices, and to prepare each other for the next evolution in the world of B2B sales.

Speaking of what’s next, there’s another evolution taking place in the world of sales. While AI (Artificial Intelligence) is a formidable change, the age of feedback and transparency is driving another change in buyer behavior. While the Information Age and the Digital Age armed buyers with the information they require to select potential vendors and better discover what’s possible, this new “Feedback Economy” is allowing them to also predict what their experience is going to be like using your products and services.

Feedback – in the form of peer reviews, has proliferated everything we purchase. Our children (aka ‘our future buyers’) are growing up reading the star ratings on the iTunes apps they download and the Netflix shows they select. My kids are actually looking at reviews of the toys they ask for on Amazon, which all contain both positive AND NEGATIVE reviews alongside the product selection. We’re all reading reviews on the online products we purchase, the restaurants we choose, the hotels we select and even our ride-sharing drivers – who are also rating us.

Feedback in the form of peer reviews is now infinitely more accessible in the B2B world, too. There’s a reason why a company like G2 Crowd, whose primary focus is on reviews of B2B tech, just took a massive fundraise.

This type of information accessibility is driving another needed change in the way sellers prospect, position, present and even negotiate. It may be counterintuitive to believe, but sellers who lead with their flaws are experiencing faster sales cycles, higher win rates and finding that they’re making life really hard on their competitors. Sellers who embrace transparency and vulnerability in their presentations – and even their negotiations – are speeding buyer consensus, and increasing deal value. It’s a new mindset – positioning your products and services as less than perfect – but without a change in seller behavior, buyers will find out on their own, and the result will be eroded trust and deals in the loss column.

How will you prepare?

Author, Todd Caponi, author of the book The Transparency Sale, has a passion for all things sales methodology, learning theory, and decision science. He’s led multiple sales organizations, owned / operated a sales training organization, helped two companies to successful exits, and won the American Business “Stevie” Award for VP of WW Sales of the Year. For more information on Todd or The Transparency Sale, check out, or follow Todd on Twitter @tcaponi.

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