Sales Enablement is a really hot topic these days. A Google search on “sales enablement” yields 1,950,000 results. A LinkedIn search on the same phrase shows that 230,595 LinkedIn profiles have “sales enablement” as a skill, along with 64 different Groups that claim to have “sales enablement” context and 1,296 Open Jobs that are “sales enablement” related.

It’s obvious that a lot of money, time and resources are being spent on sales enablement. Why is it important?

Let’s start by answering the “why” question. I’ve been in enterprise software sales for over 25 years now. And the fact is that it has never been harder to engage and sell to the enterprise (i.e., Fortune 1000 companies), then it is today. Everyone knows the statistics that buyer’s aren’t engaging sellers for up to 60%-70% of their evaluation and buying journey. The buyer can conduct research anonymously through the web and by checking with their peers. In many instances, buyer’s can self-demo or do a free trial of a software product without even speaking to a sales rep. In fact, some companies allow for the customer to buy their product without any interaction with sales people.

As someone who started selling in an era where defining and controlling your sales process was instilled in me, this complete loss of control over the sales process is quite unsettling! The first step is accepting that your buyer is in control now. The smartest thing that you can do is truly understand your buyer’s journey and align everything you do from a marketing and sales processes to their journey. This dramatic change in the seller – buyer dynamic is well accepted today, yet many companies still haven’t successfully adapted the way that they market and sell to this modern day reality.

Selling to the enterprise is more competitive then it has ever been before. As a long time VP of Sales, I consider “competition” to be any software company attempting to sell their products to my target prospects. Everyone in sales is fighting for their “share of wallet” within the enterprise. And even though it is a fat wallet, it is a fixed amount of money that the enterprise will spend on technology solutions each year. As a sales rep, my job is to convince the powers to be that my solution is more important and will deliver more value than all the other technology solutions that the enterprise are evaluating and buying this year. Or at a minimum, you need to prove to the buyer that your solution needs to be part of their overall “spend” in technology and that your solution is complimentary to their most important technology needs.

There are also more direct competitors then ever before. Why is that? Because the costs to build and launch a new software product have never been lower courtesy of the commoditization of technology and globalization of offshore development. You can spin up an instance of AWS through Amazon with a credit card and have software developers in India, China, Eastern Europe and other areas start programming your new software product immediately. It doesn’t cost millions of dollars to build an enterprise class software product anymore. And it doesn’t take a year or longer to build a new enterprise software product from scratch. It can be done in months. There are new competitors cropping up every day in the form of a new start-up that supposedly has a superior product to yours.

There are more sales people in enterprise technology sales then ever before.   And with exponential growth in the number of sales reps over the past 20+ years, there is serious dilution of talentJ The sad truth is that there are more crappy sales reps then ever before due to the sheer growth of sales positions and the lack of quality people to fill all those roles. It’s basic math. If there were hundred thousand enterprise sales reps when I started selling and now there are a million enterprise technology sales reps today, that means that the bottom 80% low performing sales reps was 80,000 and now is 800,000. I would submit to you that the old 80/20 rule needs to be updated as well. In my experience it’s more like 90/10 these days where 10% of your sales reps will produce 90% of your overall revenues due to the dearth of quality sales reps out there selling today.

There is mass confusion in the customer’s minds. When I first started selling Human Resources software to large companies, there were less than 20 companies that sold HR software to large companies. Today, there are over 1,000 different companies that sell HR related software to large companies. And they all sound exactly alike and claim to do the same things. Imagine being a customer and trying to evaluate and decide what HR software they want to buy. It must be like the teacher talking in the old Charlie Brown cartoon ( and the customer is Peppermint Patty and being put to sleep by hearing all the sales reps sounding like “wha wha wha”. How does the customer make sense out of all the noise out there and cliché technology messaging today? The HBO TV show Silicon Valley is a painful and yet hilarious reminder of how cliché we’ve become in technology (warning: there are curse words in this video clip

To summarize the answer to the “why” sales enablement is important, here are the key business drivers impacting sales organizations:

  • The Seller – Buyer dynamic has radically changed
  • More and intense competition for share of wallet
  • Easier, cheaper and faster to build a new software product
  • More bad sales reps
  • Mass confusion for the customer

Recently, I was working with a VP of Sales on a sales enablement project. He has a long and storied career in technology sales to the enterprise. When I asked him why he was investing in a sales playbook and sales boot camp training engagement with us, he replied that they had done an extensive analysis of their top performing sales teams and deals as well as their laggard performing sales teams and their deals. And their analysis showed that they needed to execute “flawlessly” from a sales perspective to win a deal and at the deal size that they wanted. Imagine that, if there was even one minor mistake committed through their sales execution they would lose the deal and never have a second chance to recover. That “flawless” sales execution is becoming the norm these days, not the exception. Fundamentally, that is “why” any strategic sales executive needs to invest in sales enablement.