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How do you get inexperienced sales reps to do the complex? Answering that question is the holy grail for sales enablement, so here I’ll take you through a case study of when Shopify introduced its Sales Academy and the steps we took to achieve our goal and educate the next generation of our sales org.

Overall it was a great success but we definitely learned some lessons along the way, so I’ll discuss how we went about it, the steps we took, and the key takeaways for the future.

My name’s Emily Payne and I'm really excited to be writing this article for a couple of different reasons. One, I really love to geek out about all things enablement and two, I love to teach people cool things, I think that's why we're all in enablement because we love to teach people.

Hopefully, in this article, I can accomplish both. We can geek out a little bit, and we can learn something. But before I dive into the good stuff, I want to tell you a story.

Let me tell you a story...

I was recently given the opportunity to teach at a local college up in Ontario, Canada, where I'm from. I was set to teach an ‘intro to sales’ course, part of the business program at the college, and the cool thing was it was mainly going to be international students.

So I thought, "This is going to be great. I get to interact with people from all over the world, I get to teach them sales, and maybe I can influence them in their career to come". I was pretty pumped about it. But then in my first class, the energy was pretty low, I was clearly the only one that was excited to be there. And I figured, "Okay, I have to do something. I've got to get people up out of their seats. I've got to make people entertained".

I did a facilitation trick that we do at Shopify a lot - I decided we were going to have a rock paper scissors competition. Basically what you do is you pair everybody up, everyone plays rock, paper, scissors, and whoever loses becomes the winner’s cheerleader in the next round.

Eventually, you get down to half the room cheering for one finalist, and the other half of the room cheering for the second finalist. I explained the game to everybody, told them all to start playing, and guess what happened?

Nothing. Nobody started to play. I realized this is mainly international students. Nobody knows how to play rock, paper, scissors and it made me think if I want people to do something complex, I have to teach them the basics first.

How do you get inexperienced sales reps to do the complex?

As we all know sales can be pretty complex, there's a lot of nuances that go into sales. So how do you get inexperienced sales reps to do the complex? This was the question we asked ourselves at Shopify. At Shopify, our goal is to make commerce better for everyone and that goal was expanding and it was rapidly growing.

We needed sales reps to come in and be able to help us reach our goals but we wanted to do things a little bit differently.

We didn't want experienced sales reps to come in and have a preconceived notion about how we should be selling our platform. We wanted to really challenge the way that other organizations had made their sales structure.

So, we took advantage of the three post-secondary schools that were located in Waterloo, the city where our enterprise office is located, and we started hiring new grads, which made us ask the question, how do we get inexperienced sales reps to do the complex?

How we did it: Sales Academy

Well, you teach them the basics, and that's what we did with Sales Academy.

Sales Academy was an internal education program that was designed to inspire new grads to choose sales as a career, and then we taught them the skills and the behaviors needed along with real-world experience in order to join our sales team as well rounded high functioning reps.

I'm going to teach you how to create your own Sales Academy program back in your office. We're going to go through:

  • How to design and structure your program,
  • How to recruit the right people into the program,
  • How to make sure that they have the right behaviors, and are modeling the things that you want them to.

And then I'll talk a little bit about the lessons that we learned when we were implementing this program.

Design and structure


Altogether, our Sales Academy program was six months long, and it was divided into three two month parts.

  • The first two months were traditional classroom-based learning.
  • The next two months consisted of a rotational period where all the participants got to shadow different roles within the organization, this gave them a lot of business acumen.
  • The final two months were real hands-on experience, we immersed our participants into the sales role. They got to own sales, full sales cycle deals, and then they got one to one mentorship from some of our senior, most successful reps.

Cohort model

For the cohort model, we decided on a group of six and we did this for a couple of different reasons - even number groups are just easier to train, you can pair them up and they're a little bit easier to do group work with.

The hypothesis

We wanted all six of them by the end of the program to join the sales team. In no way did I stand up in front of the room on the first day and say, there are six people here and only one of you are going to make it to the end. That's not what we wanted to do. We wanted all six of them to join the sales team.

But our hypothesis was, maybe four of them would join at the end, maybe one would find another opportunity within Shopify that excited them a little bit more, and maybe one would opt out - they wouldn't make it to the end of the program, or we wouldn't offer them a job at the end.

We wanted to make sure that we built in the flexibility that people could say, "You know what? Sales isn't for me", we found a lot that when we were hiring people with not too much experience, they would get into sales, and after six months, they would say, "This is not where I thought it would be. I'm out" - that's really expensive.

We wanted to do this in a way where people have the opportunity to say, "I want to try something else".


When it came to compensation, how we modeled it was we ended up going with everyone having a contract position for the six months. We didn't hire them full time, instead, we gave them a contract and said at the end of the six months, you may be offered a full-time role.

We did pay them though we gave them an hourly wage similar to what we would pay an intern. And then we gave them the opportunity to earn more money along the way, we did different competitions. And I'll explain a little bit more about the competitions in a few minutes.

Learning opportunities

Throughout the six months, we gave them a ton of different learning opportunities. We focused on things like value selling, fundamental sales skills, and product knowledge.

We didn't tell them the ins and outs of the product and make them product experts, that's what we have solutions engineers for, but we made sure they understood which personas to sell which aspects of the product to.

But because we were hiring new grads, we knew that we couldn't just make them great sales reps, we had to make them good employees. So we had to teach them professional development skills as well. Things like goal setting, and networking, and how to manage their time properly. For a lot of them, this was their first full-time role so we wanted to make sure that they were well-rounded team members.

But the nuts and bolts of your program can only get you so far. It's really the people that make the difference in a program like this.

Finding the right participants

New grads vs experienced

I touched a little bit on why we decided to go with new grads versus experienced. But again, we really wanted to challenge the traditional structure of sales. We wanted people to come in that were eager and passionate, and could look at sales in a new light.

We also knew that we wanted to not only hire people that knew sales was the career for them, but we wanted to inspire people to choose sales as a career, who otherwise hadn't thought about it. We wanted to challenge the way people thought about sales. We knew we had to become thought leaders in our community.

Community engagement

As I mentioned, we have three post-secondary schools, two universities, and one college and what we did was we started to become guest lecturers, we went to every business and sales program we could find, and we even consulted on some of the professor's curriculum.

We made sure that even if they didn't go through our program, the education could get better for them and the training could get better, so we could still have a better funnel of candidates coming out of school.

The application process

We also sat as judges and mentors on different sales and business competitions and we made sure to invest in women in tech events as well because we really wanted to encourage more females to choose sales as a career. We tried to make the application process unique as well so during the process, it was a mandatory requirement that all candidates had to submit a one-minute pitch video.

They could choose a topic or an item, whatever they wanted, and just sell us on the value of it. This let us see them a little bit in action and also let us see if people really understood what value selling was. If they didn't, could they do a little bit of research and figure it out?

Also, during the interview process, we had some of our top sales reps participate. They ran a lot of the interviews, which allowed our candidates to interact with people who had the job that they were aspiring to have. And we also had the ability with our sales reps to evaluate things like culture fit, and do these people have a passion for sales or a passion for learning?

But when you have the right people in the program, you want to make sure that they're doing the right behaviors. So we'll talk a little bit about incentivizing those. During the six month Sales Academy program, we made sure to incentivize learning, not just winning.

Incentivizing the right behavior

Learning vs. winning

Remember, I'm saying that we're trying to challenge the traditional way of doing sales. So it wasn't just about closing deals, it was about how could they learn and how could they apply their knowledge, that's what we wanted to reward.

We would give prizes for things like best presentation, or most successful roleplay or best grade on a quiz - ways that they could prove that they're actually implementing their knowledge, that's what we rewarded them with.

Individual & team rewards

We also wanted to make sure that we had a balance between individual rewards versus team rewards. We wanted to make sure we gave everybody the opportunity to show that they could be a part of a team rather than just win individually.

For example, at the end of the first two-month section, all the participants had to take a written exam to make sure that they had all the basic knowledge that we wanted them to have. And what we did was we gave a reward to the group if every single one of them got a certain grade.

This incentivized them to actually prepare as a team, and make sure everyone was going to get a good grade versus everyone preparing individually.

Reward with opportunity

We also made sure to reward with opportunity, not just money. We wanted our candidates to understand the value of new opportunities and the value of doing something different, not just monetary.

We did things like we gave them the opportunity to visit another office for a week and interact with teams that they otherwise wouldn't have met. Or we gave people one on one access to our Shopify executives - an opportunity that a lot of people in the organization didn't get.

Lessons Learned

Of course, we saw a lot of success in the program, but we also learned a lot, there were a couple of bumps along the way and a couple of things we realized towards the end of the six months that we should have implemented at the beginning.

Org-wide commitment

I'm going to go through a couple of the lessons that we learned. Firstly, we learned very early on that we needed org-wide commitment for a program like this to be successful. We needed all the leaders in the organization to understand the value of Sales Academy, so they would commit resources to it, and they would commit people to participate in that shadowing aspect.

Leadership buy-in

We also realized towards the end of the six months, that we really didn't have enough sales leadership buy-in, and we didn't get to the point that we wanted to. So we realized that we should have given more opportunity for our sales managers to really understand what the Sales Academy participants were learning and how they were preparing for a role in sales.

After all, it was our managers that were hiring out of this program. So it would have been a much smoother transition if we could have had them see really what they were working on and see them in action a little bit more, I think they would have felt more confident in hiring some of them.

Full time vs contract

We also ran into a few speed bumps with the full time versus contract opportunity. As I mentioned, we gave everybody a six-month contract, but it ended up being much more of a distraction than we thought it would. We found that the participants were actually becoming quite panicked at the thought that they didn't have a 100% guarantee they were going to get a job at the end of this program.

Even when we got to the midway point, they were much more focused on the security of a full-time offer then we thought that they would be, so they weren't as focused on the learning aspects of it as we would have liked them to be.

What’s out of your control?

We also learned a lot about what was out of our control in the organization. With Shopify, the business is growing so quickly, that by the time our participants were coming to the end of the six-month program, we were already reevaluating whether or not hiring new grads was the right option for us. Even our expectations of our current sales reps were changing so quickly that the content we had in Sales Academy quickly became outdated in just a matter of months.

So it could still be a functional program, we just had to be really aware that it was going to rapidly change every cohort.


We learned a lot. We applied all the knowledge to future programs, we even started sponsoring other local tech companies to do Sales Academy programs like this and taught them how to do it. And now hopefully, all of you can learn a little bit about it.

Our original Sales Academy cohort, pictured above with me in the middle, was a group of young, eager, passionate individuals who above all else really wanted to learn.

With our focus on the basic fundamental skills, and giving them real-world experience, we were able to train our next generation of sales reps who are still making an impact today.

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