Calling on Data
Published in

Calling on Data

Q&A with Matt Collaton, Head of Outbound Sales @ Shopify

Today Matt Collaton joins us from Shopify.

Shopify is a hypergrowth e-commerce company that develops software for online stores and retail point-of-sale systems. Since 2006 they’ve grown from a team of 5 working out of a local coffee shop, to a team of over 2,000 working in 5 offices across North America, and can call thousands of well-known companies like Citizen and Tesla as customers.

Ben: Thanks for joining us. I know you, but for readers it’d be helpful for you to introduce yourself and tell us where you’re at today.

Matt: Ever since I graduated university I’ve been in tech sales, specifically internet companies. I was with a company called, then Careerbuilder for seven and a half years, then four years with LinkedIn building their acquisition salesforce. Now I’m happily at Shopify, as of two months ago.

Here my role is head of our outbound sales team, which is ~24 people.

There are no named accounts here or anything like that. We’re very lucky to have a great funnel for our inbound reps, they focus mostly on site inquiries. The outbound reps are going out and finding the competitive business to take market share or approaching new merchants looking to breaking into the e-commerce space. So that’s what our team handles, that net new acquisition or migrating customers over from an existing platform.

Shopify’s Ottawa Office

Ben: Talk to me about your sales cycle.

Matt: Typically 75 to 90 days, it can stretch on beyond that for some of our more complex sale cycles.

We reinvented the traditional SaaS based sales model a little bit, and we’ve gotten rid of the SDR/BDR function here. So customers deal directly through outbound prospecting with the account executive or enterprise sale rep that is going to take them through the entire evaluation, start to finish.

During some of the more technical demonstrations or migrations we may bring in a solutions engineer who help can provide an outline of requirements, but you’re typically looking at a 20 to 30 minute discovery call, then a demo and sometimes a separate technical demo of IT or other stakeholders need to be involved. So you know I’ll say three to four touch points on average.

But that’s once we have discovery call scheduled. It can sometimes take 15 touches to even get that right person to commit to a call.

Ben: I’ve asked other folks what’s in their toolbox, but everyone is pretty much running on the same stack, with a few variations specific to their business. I’ve got another idea.

I want to know what the hardest thing is that you and your team do on a daily basis.

Matt: It’s hiring.

Every time you think you’ve got it nailed, something throws you a curve ball, and you’re right back where you started. Right now in general I’m thinking in the region we’re in right now, it’s a great tech hub here in Waterloo, you know a lot of people refer to it as Silicon Valley of the North. Waterloo is one of the world class engineering universities.

But what you don’t have are universities or colleges teaching Sales. So one of the challenges for us is creating a solid pipeline of people who want to be in sales. We’re trying to do stuff within the community to just raise awareness, so we partnered with some of the local resources here to help get the word out about opportunities, tech sales openings, and educate people on it. It’s a supply problem, and it’s a skill set problem.

You think you have it nailed — you know this is your profile, and we’d get people from this company with x-number years of experience, then two months later you realize, maybe the need changed, and so the profile has to change. We’re at different points of maturity in the market than we were a year before.

Ben: If you close your eyes and picture having a new tool solve any of your problems, would it be hiring?

Matt: Yeah I would say so. Something to help solve for unconscious bias, solve for fit and predicting the likelihood of this person being productive and loving what they do.

Ben: If you think about the marketing funnel or sales funnel, you understand your referral source so that you can attribute any sort of lifetime value metric to the actual source of acquisition. That way if you have a customer that cost you a lot to acquire and doesn’t create a positive ROI, you know that might not be the best channel to invest in.

Matt: There are a lot of organizations who are trying to get there, but don’t know if they’ve done it effectively.

Ben: You can you can talk all day about the best intentions for a new process, but it has to be executed, and executed well.

Matt: Finding great people and then devoting the resources and the time to develop those people is critical.

So much of a new hire experience is critical in the first few weeks, where you’re providing a foundation and the ability to really believe they made the right decision to join the your organization.

We’re going to support them as long as they put in the effort.

Ben: Within the first four to eight weeks, how often are you sitting down with your direct reports and going through calls and coaching them in 1-on-1’s?

Matt: I’ve two great leads who manage our website salespeople on a day to day basis, so I’m dealing more with group initiatives, reinventing our on-boarding and training is where I’m focused.

I will work with a group that starts next week, doing a session on social selling and how to leverage networks when they’re reaching out.

Throughout the first four weeks, I’m probably spending about four to five hours a week coaching.

Ben: Per rep or in total?

Matt: Collectively.

Ben: There’s an ever changing cost/benefit analysis of training and coaching mid and low performers versus the cost of acquiring and on-boarding new reps. I want to hear your perspective on that.

Matt: Yeah so we went through a lot of this at LinkedIn, where we would ask ourselves, where do we focus our time, effort, and energy? Is it A players is it C players, is it bringing the middle up?

We found that the majority of our people kind of fell into that B category. Like your A’s are outliers, maybe top five or 10%, your C’s should be your bottom (hopefully less than 10%) but you know maybe bottom 10%, and then then there’s that big bulk of B players that makes up kind of 70 or 80% of pretty much any sale org.

They group tightly together and we focused our energy on moving those. So figuring out, if we can make a 10% impact on that group versus making even up 50% or 100% impact on other two groups, the results of the returns will be greater. So we really focused our time and energy on upscaling B, B- or B+ players and attempting to push them to the next level. A lot of that effort was around coaching skill development; personal development plans, helping them with individual gaps that they have, but also bringing out their strengths, accentuating those, and aligning them with senior mentors.

Ben: Tell me a little bit more about the mentorship program.

Matt: They do deal breakdowns together, “here’s my pipeline, here’s my forecast, here’s what I’m doing.” A lot of times the mentor just acts as a reflection, holding up a mirror, asking, did you pose this question, do we have the right people involved. They are going back into deals, reopening and exploring it, making sure they have those things and [if anything is missing] then we proactively try to change that behavior going forward.

Ben: Talk to me about time management — you’ve only joined Shopify 2 months ago, how are you fitting learning a new product in with everything else?

Matt: It’s been a huge shift. I’ve always been in the talent and internet recruitment space, so going to the commerce space I had to really up by my level of education; competition, who’s involved, etc.

You’re going from selling to HR to selling directly to co-founders or founders. Their day, vs. the reps here, they don’t necessarily have the same hours, like 8:30am to 5:00pm. Some of them are getting up at 11:30pm or 2 in the morning for a call with us. Or some being in California, who may only have you know 9pm Pacific available, we want to be as merchant-centric as possible, we want to provide a good experience.

It’s actually been a lot of fun learning so much each day again, listening to sales calls, listening to some of these pipeline interviews and learning different elements of this sale process. It’s really helped open my eyes.

Ben: There’s something about learning that sparks your neurons to fire in way that is very different from day to day tasks. It’s engaging.

Matt: Yes, it’s super enjoyable.

Ben: Of the sales leaders you follow, what are they using as guiding principles, or what are their strengths?

Matt: The leaders that I’ve really seen in action don’t take themselves too seriously. There’s still an idea of humility. We spend so much time together, as a sales org and as a team, [the great sales leaders] make it enjoyable, they make it fun. And they’re still able to rally the troops towards that aspirational goal.

Every organization puts a bunch of goals on the wall but then they never talk about them or don’t hold each other accountable to them. The leaders that I’ve seen have done a really good job breaking that down and making it actionable for everybody, from pipeline employees all the way up. They create a culture where if they say they’re going to do something, they do it. They follow through.

It’s consistency, predictability.

Ben: Changing course a little, I want to hear what what you would remove from sales. It could be an acronym, it could be a tactic, it could be anything that you just feel is just snake oil…what would it be?

Matt: It’s funny, our team was talking about revamping the discovery call the other day, in terms of how we approach the process. Somebody said, “I like to say, tell me about your business.” That question as an opening just makes the hairs on the back of my neck stand up.

I’ve been asked it so many times, then I go into my canned, corporate response I’ve been rehearsing 100 times. You’ve done your preparation and in the discovery process you’re asking questions that are relevant to the person on the other end, but you’re starting with this open ended question. I can’t stand it. I think it should be eliminated for BDR, SDR, AE vocabulary. Because if I’m on the other end of that call, I’m thinking you’ve done no research or preparation.

It’s something that I’ve been trying to get out of people’s vocabulary for years.

Ben: Your a team lead at one of the fastest growing tech companies on the planet. What are your biggest opportunities for growth as a sales leader?

Matt: Growth was one of the major motivating factors of making the move from LinkedIn to Shopify. It’s the first time in my career that I’ve actually worked for a Canadian company and a company that is really committed to growing their business globally, but out of Canada.

For me what that provides is a platform, that as our sales force grows hopefully I’m able to grow with it and take on more responsibility, take on new challenges. I think the level of interaction with having sales ops partners here, biz ops partners here, marketing, sales enablement…in all my past role those were resources that we leveraged from the US, that we leveraged from Chicago, from San Francisco at LinkedIn.

I never really had exposure to those parts of the business. They would fly up once a quarter and do their thing, and then we’d kind of be forgotten about as a region for a few months. So for me, having everybody here and the cross functional projects and relationships we’re already working on two months in, it’s a night and day difference in terms of my involvement, and my learning curve. So hopefully I can continue to ride that and do what we ask our reps to do: get better each day.

Ben: So parting words — what are the gems that you’ve learned over your years running sales teams?

Matt: You’re going to fuck up, you’re going to make mistakes. It’s okay, just learn from them, get better. As managers we want you to fail, we expect it at first, but we put you in that position because we feel you are smart enough to figure it out.

Ben: Be comfortable with failure.

Matt: Fail often, fail first, fail a lot but just everyday, every time you fail, learn something to help you get better. Don’t make the same mistakes over and over. Look at yourself in the mirror, seek feedback, ask your family or your significant other.

I’ve got some of the best feedback from my wife who knows me better than anybody.

Look for feedback at all different places.




Defining the category of intelligent call optimization. We help sales managers build more effective teams and processes. Learn more at

Recommended from Medium

“5 Things I Wish Someone Told Me Before I Became the CPO at eBay” With RJ Pittman

Dear America: Asian Americans Are Not Your Model Minority

Weee! closes $425 million Series E led by SoftBank

Could Place Management Be Just The Medicine Sick Retail Needs?

Android vs iOS: Which mobile platform best serves Point of Sale?

Three Quality Management Trends to Watch in 2021

Segway ES4 Electric Scooter for $350 With Coupon ($749 retail)

India and the Internet

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Ben Apel

Ben Apel

More from Medium

Out of Office: Experiences to Guide Success for Remote Work — Natalie Cantave

Natalie Cantave smiling with pink, red, and black flower shirt on.

Breaking the silence — mental health of startup founders

6 Trends Shaping the Coaching Landscape in 2022

Let’s look at some more of this article.