Can Millennials Sell?

Editor’s note: Today’s post is from Docket CEO Jason Wesbecher. This will be Jason’s fifth post on the Funnelholic.


Try searching for some combination of “millennials” and  “selling” and you will find something surprising. Of the million Google results, the overwhelming majority of content is about selling to millennials. Selling them anything: mortgages, insurance, cars – you name it. There is an entire cottage industry built around teaching old-line industries how to identify with this peculiar new generation and their psychographics, ad preferences, mobile habits, and decision-making processes. It’s no wonder, when you consider that the 80 million millennials represent the largest generation in the history of the US.

However, there has been very little public conversation about the other “millennials” and “selling.” Which is to say, are millennials well suited for sales positions? Can they sell? It’s an important question to ask, as the 4 million millennials entering the workforce each year are – demographically speaking – well suited for employers’ explosive demand for entry-level sales positions.

The practical answer to the “can they sell” question is this: on paper, millennials are perfect for the job. They are mobile-first, social natives who love software. Juxtapose this against your average Gen X salesperson who still speaks lovingly of the Blackberry’s tactile keyboard, who maintains maybe just 1-2 social properties, and who prefers the face-to-face meeting to the digital one. Compared to Gen Xers, the millennial generation is much better matched for the profound change that is occurring in how customers buy things.

Today’s buyer does the majority of product research before speaking to a salesperson and, by extension, prefers to acquire their vendor knowledge from content pieces as opposed to the sales pitch. What this means for the modern sales rep is they must be as adept at digital marketing as their predecessors were at cold calling. Truly great salespeople create their own content – tweets, blog posts, LinkedIn updates, Instagram photos – and they comment on and share the content of like-minded folks in their industry. What generation is better suited to engage customers in this fashion than millennials? They have been living online for the last half-decade creating their personal brands. They implicitly embrace the idea of sharing. The idea of creating a personal brand and sharing it is largely foreign to the Gen X salesperson.

The other thing that millennials have going for them is their belief system. They tend to be a highly principled lot, who have the capacity to get extraordinarily focused on the cause. This could be wage inequality or antibiotic-free meats or clean drinking water. Or it could be your product or the mission of your company. Some of the best salespeople I have ever met share a common trait: their unwavering, unflinching, blinding belief in what they are selling. You simply can’t sell something effectively if you don’t believe in it. Millennials have the ability to believe and believe hard. The trick as an employer is to take the time to explain why they should believe. Why is this problem that we solve so important? And why are we uniquely capable of solving it for the world? Articulate that to your millennial sales team and watch them soar.

There is a bit of serendipity happening in the labor market right now. Software as a Service has changed the focus of how selling is done.  These days it’s about selling to the user versus selling to the executive buyer. And there is a heavy emphasis on “try before you buy.” This is causing a pretty rapid shift from the traditional outside (“enterprise”) sales model to the inside (“corporate”) sales model. And by design, the inside sales rep tends to be slightly more junior. Enter the millennials. A generation that is uniquely suited for today’s sales environment. Can they sell? They’ve been doing it for longer than you thnk., content selling, sales, modern salesAuthor: Jason Wesbecher is the CEO & co-founder of Docket, a tool that helps salespeople measure the intent of customers based on how they engage with their sales collateral.