A fresh look at sales - it’s mainly about one thing


Man outside - Jordan Gregoris


Long-time Shopify salesperson Jordan Gregoris says we may have the wrong idea about what salespeople do through Hollywood movies and intrusive dinner-time calls, and good sales is mainly about one thing. 


By Jordan Gregoris, Shopify Cross Sell 

After a long day, you finally sit down for dinner.

Before your first bite, the phone rings.

Window sales? Duct cleaning? Real estate? How did you enjoy those conversations?

Over time, we’ve all had negative interactions with salespeople - interactions where there was no customer empathy and no relevant value communicated. Instead, you received a raw and uninvited pitch.  

When sales is done well, however, it’s a win-win for both the customer and the salesperson, and it’s the reason I believe sales is a craft that is by its nature, positive-sum.

Sales - the helping skill

After four years of selling at Shopify, I am happy to admit that any assumptions I had about sales have been flipped on their head. Often it's the kind hearted, respectful, even soft-spoken team members who consistently win the most business. 

Contrary to popular belief, sales is not a pushing skill, it is a helping skill. The best salespeople are far more focused on the customer than they are on themselves. They enjoy the process of finding and helping. 

Did you ever watch Boiler Room (2000) or The Wolf of Wall Street (2013)? These popular films take us into the lives of salespeople who put their own interests over their customers' interests. To them, customers are not people, just potential business - business that could be ignored right after a customer signs on the dotted line. This isn’t sales, it’s manipulation. 

When Hollywood poorly represents salespeople, it also affects our image of what a sales professional is like, and worse yet, what their motivations are. The intimidating cultural trope of the unempathetic salesperson has likely deterred a lot of potentially amazing salespeople from ever getting started. 

Sales is one of the most important professions in the world and arguably, the most valuable skill.  Can you imagine how a company would function without salespeople who help customers understand how they can best use their products in pursuit of their objectives? In this way, sales is like the connective tissue of the business world.

When sales is a win-win

Imagine you are working diligently between family gatherings through the holiday season, making every effort to ensure that the year closes strong for your customers and the business. 

Both parties understand that an agreement needs to be made before midnight on December 31 and commit to a decision. Then the work really begins: multiple proposals, stakeholder calls, and eventually, you get the OK. An agreement is reached right before 8 p.m. on New Year’s Eve and the customer is thrilled with the new partnership. 

Then, your phone rings… 

It’s your boss calling you to tell you that the team made their goal for the year. What a feeling.

Then, the phone rings again…

It’s your new customer’s CFO calling you at 10 p.m. that same evening to say how excited they are and to congratulate you on your winning proposal. 

You may think this sounds a little too good to be true, but this actually happened to me in the final hours of 2021. 

These types of experiences have shaped my attitude for what successful sales looks like. Each opportunity is positive-sum, not zero-sum. The best salespeople negotiate with, not against.  

Sales professionals excel at finding people with relevant challenges and helping them achieve their desired outcomes. This takes curiosity, integrity, and empathy in spades. It's why sales is a craft not just a job, and the craft of helping merchants is the central ethos of Shopify’s mission.

Sales at Shopify

Shopify is critical to its customers. As Shopify President Harley Finkelstein likes to put it: “Shopify is the first thing a business opens in the morning and the last thing they close at night.”  

Serving as merchant “mission control,” the Shopify platform now includes multiple solutions for merchants from payments, lending, shipping, to consumer apps (like ShopTM).  

The combination of being mission critical for our customers and building solutions that span multiple categories, wrapped in our mission of helping merchants succeed, makes Shopify by far the most interesting company to sell for. But what truly sets Shopify apart, is its dedication to developing sales as a craft within this unique environment.  

If you’re interested in sales at Shopify, check out Revenue School. This four-month paid program is for university and college graduates who are interested in learning the nuts and bolts of sales at Shopify and becoming eligible for a full-time role.