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.

5 Tools I Wish I Had When I Became a Sales Rep feat. @MarkRoberge

Sales tools, sales productivity

Editor’s note: Today’s post is from Mark Roberge, CRO of the HubSpot Sales Division. One of my all-time heroes in modern sales. Please enjoy. His last post on the Funnelholic: 4 Habits of a New Generation of Top Sales Performers drove so much traffic and interest, I had to bring him back again. [Read more...]

Where Deals Go to Die: 5 Sales Administration Steps You Should Automate Today

sales enablement

Today’s guest post is from Chris Bucholtz, content marketing manager for CallidusCloud and a speaker, writer and consultant on topics surrounding buyer-seller relationships. I worked with Chris a few years ago and he is brilliant. Oh and he is the kind of guy you can talk to about anything including baseball, model airplanes, and the Tuskegee Airmen. Here we go:

Anyone who sells in large companies has seen it: a deal that races through its early stages and seems like a sure thing, then abruptly grinds to a halt – not because the buyer suddenly got cold feet but because the salesman has become hung up on internal processes.

These administrative tasks are important – your company wouldn’t do them if they were not. They provide a means of control for sales managers, a record for marketing to evaluate its performance, and even help out the sales rep once in a while by offering up some insight about a customer. [Read more...]

Top 5 Best Practices for Email Subject Lines

Today’s post is written by Katy Creates, PR Manager at ContactMonkey, a smart email tracking for Outlook, Gmail and Salesforce, based in Toronto.

How long do you spend on writing the perfect email subject line? 10 seconds? 10 minutes? 10 hours? New research suggests that you are wasting your time.

Email tracking service, ContactMonkey, has analysed over 30 million emails to find out what works best for their users. It is the first time anyone has ever collected this amount of data.

They have now released their research on the best performing email subject lines specifically to help salespeople convert those leads into wins.

1. When in doubt, worry less

Time spent thinking about the perfect subject line is time wasted. There is no perfect subject line. Just a simple Re: got a 92% open rate according to the research.

2. Be direct

Longwinded marketing speak fared very badly. It might work for a blog post but your subject line should act as a taster, not the main course. As an example, a long subject line like: “10 secrets for accelerating business results” achieved only a 10.92% email open rate. [Read more...]

When Ari Gold Sells “Silo” – A Sales Lesson From Entourage

solution selling, decision makers, sales tacticsI took a break this weekend. I don’t watch movies that much anymore. I am one of those people that when I have time, I binge watch TV. So this weekend I watched some Entourage on HBOgo.

There was a scene (Season 4, Episode 10) that caught my eye where Ari Gold, the agent for the star of the show, Vincent Chase, has to go sell a movie to the studio boss where he has absolutely no chance in hell. I don’t want to bore you on too much background. Just focus in on how he sells the movie. [Read more...]

4 Habits of a New Generation of Top Sales Performers

The New Sales PersonEditor’s note: Today’s post is from Mark Roberge, CRO of the HubSpot Sales Division. One of my all-time heroes in modern sales. Please enjoy. [Read more...]

Sales Organization Design By The Buyer And For The Buyer (The Webinar)

I am a big believer that the person(s) who should design your sales organization should be your buyers. Too many times we try to apply “something that worked before” or an out of the box process. Instead, your goal should be to craft sales AND marketing deliver an experience that your buyers want to have. Revenue will grow as a result. Here is a webinar I did with eCornell on the topic. If you want to read more about my take on the topic, check out Why You Should Your Buyers Design Your Sales Organization.


Craig Rosenberg is the Funnelholic and a co-founder of Topo. He loves sales, marketing, and things that drive revenue. Follow him on Google+ or Twitter