Succeeding as a Remote Company: Lessons from Shopify

Succeeding as a remote company

This article on succeeding as a remote company is based on an interview with John Riordan, Director of Support, Ireland at Shopify, which took place before COVID-19 changed the world and how people work. Many of the practices and suggestions outlined below have taken Shopify years to refine. While your transition to and experience working and managing remotely may not be as smooth as Shopify’s, these practices and ideas will help you lay the foundations for a sustainable remote work culture going forward.

When I speak with John Riordan, Director of Support, Ireland at Shopify about how the Canadian eCommerce giant works remotely, I break the first rule of Remote – I am two minutes late for the call. As someone who has been in the remote work space for the past 20 years, either working and managing remotely or advocating for it, John has spent many minutes waiting for someone on Zoom. He isn’t happy about it. 

Waiting for someone “from the office” to show up on a call is a pattern he has seen in hybrid teams time and time again. Remote workers tend to turn up on time more often and are more engaged than office-based workers. “It’s not their fault; there are just so many distractions in an office environment.” 

Punctuality and focus are just two of the many benefits of Remote Work, which John will be quick to point out the moment he is asked whether companies should consider it.

The Irishman is at the collision point of two planets where the company at large is mostly office-based, while he heads a division of more than 300 customer support reps who are fully remote and now spread across all 26 counties in the Republic Of Ireland. After successfully setting up remote working teams in Ireland, the process was repeated in New Zealand. John, who joined the company three years ago as the first fully remote senior executive, has played a significant role in the successful scale of the remote workforce in both countries.

In this exclusive interview for the Boundless blog, he shares what he has learned about what keeps a remote workforce happy and engaged, and how to scale it. 

How Shopify became remote

For the first five years of its existence, Shopify was just another co-located office-based company. Started in Ottawa in 2006 by Tobias Lütke, it had no intentions of introducing remote work until it became a necessity. As more international merchants joined the eCommerce company, more customer support representatives found themselves having to work the “graveyard shift” to cover for distant time zones. Unsurprisingly, coming into the office in those hours had an adverse effect on people, and the attrition began to raise. “There was a lot of disengagement and dissatisfaction in that group, relative to the rest of the company.” 

There had to be a solution to this problem. If people were allowed to at least work from home in those hours, maybe it would work better. The concept of remote working was gaining traction at other companies, so Shopify decided to try it. They chose to do so outside of Ottawa. 

the five keys to succeeding as a remote company

“A few of the leadership team went to a place called Kingston, Ontario, which is about two hours away from the Canadian capital. It’s a college town on Lake Ontario with a fairly young population that would have found Shopify a cool enough company to consider working for it under such an arrangement.” 

It worked. For the following two years, customer support reps worked at nighttime and serviced merchants around the world. As steady international growth continued, it was time to consider hiring people overseas.

Shopify looked at a few places in the UK and Ireland and, after a few pints of Guinness, settled on Galway, Ireland’s third-biggest city, boasting a large student population. It was the summer of 2015, and the Irish operations started off with 50 customer support reps who all worked remotely. “It took a year for it to hit the stride. By the summer of 2016 everyone was sold on this being the place.”

By the time John joined as Director of Customer Support for Ireland in 2017, there were 150 people doing customer support from all over Ireland. It had been three years of experimenting with a hybrid workforce, and Shopify had been sold on it. “That’s because they had seen there was a method to the madness.” What is that method exactly?

Raise and act on concerns

For someone who has become a prolific advocate for remote work and sits on the Board of Grow Remote, an Irish non-profit organisation, John will never sugarcoat this way of work or suggest it works universally. “It’s not for everyone and co-located office-based companies would find it particularly difficult to make all the necessary transitions.” 

Even by the time he started at Shopify, three years into the company having a hybrid workforce, some problems needed ironing out. As the single senior executive working remotely — the others were all based in the HQ in Canada — John would often find himself the only one calling in to meetings. Nine or ten people would be sitting in a meeting room on the other side of the screen. 

Within a few weeks, one of the leaders in the head office asked John how he was getting on.

“Well, I’ve met you all, found you all to be incredibly nice and polite people. However, when I am the only person on the screen on the wall, I find you to be insular and rude.”  

The frustration had been building up in John. It had started with seemingly small things like side jokes or comments about a hockey game the previous night that John wouldn’t get. It would be more significant things as well like not everyone looking at the camera when John spoke, instead staring at their laptops. Even though they may not have meant it, John had increasingly felt excluded in subtle ways. 

When asked, John didn’t hesitate to be honest. 

Shortly after that, the Shopify leaders decided that everyone should call in separately for that meeting from various places in the office. While it may appear as a small thing, that change made a big difference for John, leveling the playing field for him.  

Home office setup is key

It’s around this point of our conversation that John realises he hasn’t turned on his camera. As he apologises profusely for breaking another fundamental rule of working remotely, I say we should call it even – we all make mistakes.

functional home office is key to Shopify's success as a remote company

The first thing I notice as he turns on the camera is the big Shopify sticker behind him. It took him 24 hours and €30 to get it produced. It’s the final touch to a home office setup, which from what I can judge through Zoom, is a much better setup than many office desks I have occupied. (He has since written about his setup, which includes a virtual tour of the office).

Functional home office setups, something which many companies may disregard, are held to high regard in Shopify. The company doesn’t want people working from kitchen tables or couches and famously asks new remote workers to video their home offices. No wonder then that John has a particular dislike for cliched stock photos that are meant to be depicting people working remotely by showing them lounging on couches. “The reality is a much more professional and considered home office space.”

“We don’t do this out of fear of getting an inspection from the Health and Safety Authority. Rather, it’s because we know that working remotely will be sustainable going forward only if we make sure our people have the best set up in the long term.” Guidance on good posture, and furniture that prevents musculoskeletal problems are just the start of that.

People who have existing medical conditions that require a particular setup can provide medical notes to Shopify, which then commissions an external ergonomics provider to visit the worker’s house and make recommendations. After the ergonomic assessment comes in, Shopify pays for the required setup, whether that is a unique chair or a standing desk.  

Encourage people to go offline

Putting extra care for the health and well being of remote workers is paramount at Shopify. It’s one of the challenges John focuses most on as a leader of remote teams. He knows firsthand that when people do not have to commute home, it’s easy to keep working.

“One of my most important duties is to encourage people to stop working at the end of the day.” 

To do that, John takes the lead in exuding control to stop working himself.

The day before we speak, John had been working on a presentation he was to give the following week. With his family out of town and nothing exciting to watch on TV, he had decided to keep working on the slides after work hours. As he did, he quickly realised the sort of message he would be giving to his assistant who lives in Montreal: working late is okay. 

It had been a few weeks before that night that Shopify’s CEO Toby Lütke, posted a thread on Twitter about how he worked 40 hours a week and Shopify’s success hadn’t been built on anybody working 80 hours. 

“I had to signal to her very clearly that this was an exception, and there was no expectation from the leadership that anyone works at night time.” He jumped on a call with his assistant and explained all that. 

“When working remotely, you sometimes end up with these kinds of laughable scenarios where you almost have to ask permission to work late.” 

At this point in the conversation, we get to the gist of what has made working remotely successful in Shopify over the past years. Part of it is this kind of over-communication. At the bottom of it, it’s trust. 

You have to trust wholeheartedly

Any article you read about succeeding with a partial or fully remote workforce, will state that trust is at the core of it (in our current situation, the trust employers have for their employees is more critical than ever; we have already written about that and you can read more about it here, here and here). In Shopify, trust has become part of the company DNA.

It starts with every leader in the company confronting a very fundamental question: 

“Do I have the capacity to trust?” 

John is honest that he struggled with this question himself when he first joined Shopify. He had experienced first-hand workplaces where command and control reigned, and trust was just a word people used. He brought that baggage with him when he first joined Shopify, which he realised early on.

trust is at the centre of succeeding asa remote company

Shopify has a program called “On your own development” under which every employee can order any business book they would like to read and the company pays for it. Whether the book can potentially enhance someone’s business knowledge, or it is for self-development purposes, it doesn’t matter. Employees buy it, expense it, and the company reimburses them, no questions asked. 

As a rational human being, John’s first question was what the limit was for the number of books that were allowed per employee or year. “The answer I got was a question in itself: Why would the company put a limit to books an individual can buy when there is a natural limit everyone has on reading. If you’re the type of person who reads five books a week, and you want all of them to help you develop personally and professionally, so be it. Someone else will be the type of person who reads one book a year, and they will only buy one.” There was no point in artificially constraining people’s development.

“I remember thinking, that’s it, I’ve just asked the dumbest question because I showed my true colours of lacking trust by asking the question I asked.” 

Behind John, to his right, I see a stack of books. I ask him what he is currently reading.

Fanocracy by David Meerman Scott and Reiko Scott, Start With Why by Simon Sinek, Head Start by Ian Price, Renaissance Nation by David McWilliams and John’s current favourite book, The Globotics Upheaval by economist Richard Baldwin. 

John estimates the company probably foots a six-figure sum book bill each year. The immediate result of that is that the company is a magnet for external ideas. There are many channels on Slack, which are specifically created so people can share snippets and ideas from the books they have read. By allowing people to determine what they need in order to develop and not put a limit on the spend for it, signals the trust the company has in people.

Communication, collaboration, transparency

How does trust manifest in day-to-day work? To maintain it as a reality rather than just a word, John believes communication, transparency, and collaboration have to always be in place. “If you have these as spokes, you have a trusting spine.” A treasure trove of anecdotes, John shares another example where this shows.

At the time, he is in the process of creating the Shopify quarterly business review. “In most companies, it would be created by a senior leader working with one or two other people. The senior leader decides what the message should be, and they put it together.” 

Not in the case of Shopify. 

John has 40 people involved. He has explained to each one of them what he is looking for, he has put it in a GoogleDoc and has sent it to everyone to put down their contribution. Each one of them is allowed to bring in an active debate on any of the points. 

Maintaining trust at the core means rethinking everything that a company does and communicates, as a lack of trust can manifest in much simpler ways than dictating the content of a quarterly business review. It can start as early as the first weeks of onboarding. 

“When you impose rules, regulations, constraints, and tripwires as part of onboarding, you’re inadvertently saying “there are aspects of how you work that we don’t believe you can be trusted to control, so we need to do it for you.” 

Before anyone thinks that Shopify doesn’t measure the effectiveness of people’s contribution, John is quick to share how regulation has been embedded on a team level. 

Rely on team level self-regulation 

John’s division of 300+ customer support representatives is split into 10-person teams. In each group, people start at the same time, have a quick jumpstart meeting, stay in touch throughout the day and then finish at the same time. It makes everyone aware of how others are doing. They can help each other but also spot if something is not quite right. 

imposing too many restrictions during on boarding can diminish your success as a remote company

If someone isn’t there at the start or end of the day, isn’t participating in the team channel, is shirking work, as opposed to taking action, it becomes very obvious to their peer group. “Humans are good at spotting spurs.” Shopify nurtures team self-regulation by focusing on team performance instead of individual performance. 

“We will never scold anyone because on average it takes them half a minute more to deal with a customer case than it does other people on the team.”

However, if anyone simply doesn’t have the chops to work this way or is purposefully taking more time and not doing their fair share of work in a team of ten, the other nine will know. “People will quickly self identify as people that can do this or not. And if they have realised they can’t, they wouldn’t be able to last long on the team.”

It’s why John doesn’t look at the attrition in the first six months of someone’s employment. “I’m not really concerned about people that self select within the first six months to leave. I consider that to be a gift.” He is quick to assert, however, that attrition within the first six months is considerably lower than the industry average.

Making remote work work continues to be an every day goal for John and Shopify. As the framework and practices are constantly improved in how the remote workforce is managed, what remains the same is the respect for people, the steadfast support and enablement to grow and do their job to the best of their abilities and the relentless trust that they will do the right thing. It’s the best thing any remote employer can do for their employees. 

At Boundless, we believe that legally and compliantly employing individuals wherever in the world they are based is fundamental to succeeding with remote work. We make it possible for you to do that in a growing number of countries, including Ireland, the UK, Denmark, Portugal, New Zealand, Singapore, and Australia. Learn more.


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