Shopify exec: The 4 secrets of successful digital-first companies

What is work, really?

At its simplest, work involves exchanging time and effort for a paycheck. But is it really that balanced? For as long as we can remember, employees also committed to living within commuting distance of their office—which meant their work dictated where they lived, socialized, and laid roots. Multiple generations have been tethered to one place simply because of a corporate office lease.

But a funny thing happened during COVID: the world realized that a centralized physical space isn’t actually a requirement to do impactful work. The concept of “office centricity” is over. Shopify (where I work as VP of employee experience) is now fully remote—a decision we made in May 2020.

Many companies went remote during COVID. To them, this meant working from home while waiting for an ever-changing “return-to-office” date. But we asked ourselves, “what if we rebuilt our company to let employees physically center their lives around what they wanted, instead of our office leases? And how can we do this while maintaining a universal employee experience?” We chose to seize the opportunity, going all in on digital-first work. We steered clear of an opt-in model where employees can choose whether to work from home or the office, which can lead to an uneven playing field when it comes to opportunities and seats at the proverbial table. Because of these decisions, we are now Digital by Design. 

Here are four ingredients of a successful digital-first company. (Spoiler alert: it requires much more intentionality than digitizing your old office perks.)

Prioritize freedom and flexibility

When I was commuting, the odds were 50/50 whether I’d make it home for dinner with my wife and daughters. Every night, I’d get the text: “Should we wait for you?” It was always unbearable to answer. Since working remotely, I’ve had meals with my family every day except for when traveling. We’re creating new weekday traditions in my home, like playing board games and helping with homework. Family is what fuels me, so this has fundamentally changed my life. 

This is the type of freedom that remote work unlocks: you can build your life around what fuels you. For some of my colleagues, time outside of their house or apartment is what fuels them—and remote work unlocks their ability to pop into a coworking space, build social time into their day, or even work from abroad while ticking off their travel bucket list. 

If your team is used to in-office perks like foosball tables and free beer, remote work can seem “blah” at first. But that’s only until they figure out that their life no longer revolves around their workplace, it revolves around them. There are still foosball tables available, but instead of in an office tower, they’re at your neighborhood pub. Amazing lunch options now come from your local deli or taqueria. Employees can choose where they live; how they schedule their time; how to design their ideal workspace—all the way down to the thermostat setting! 

To help with that ideal workspace, consider creating a spending account for each employee. We call ours the Lifestyle Spending Account, and it empowers our team to spend their budget on whatever they choose—acoustic panels for soundproofing their work area, a neighborhood gym membership, a meal delivery subscription… With this setup, your employees get to pick custom perks that work for their specific needs, rather than the one-size-fits-all office benefits.

When you can choose your work environment, the option to travel becomes far more feasible. We launched a program called Destination90, where employees can move to and work from a different country for 90 days each year. It’s a chance to experience new perspectives, and stay energized and engaged which often leads to people doing their best work. This summer, my family and I are heading to Japan. There, we’ll be immersed in Japanese language and culture while spending time with our family that lives there, all while I continue to work. Some of my colleagues have ventured to Europe, South America—all over the world. This isn’t working “abroad,” this is simply working digital first. 

Continue to value in-person connections

Remote work untethered us from a physical space, but not from each other. Being digital first doesn’t mean you shouldn’t value occasional moments of IRL time.

A lot of people will say, “Oh, you mean a hybrid model, working at home and in-office.” No, I don’t mean hybrid. That would mean still centralizing your life around a viable office commute. I don’t think hybrid is the way forward.

Build in periodic IRL time for meaningful and intentional moments of connection, not just people working next to each other at an office two days a week. We’ve invested in spaces around the world to host these moments. At least twice a year for a few days each time, we encourage teams to meet in person, to disconnect from their screens and connect with one another. We use this time for in-person brainstorming, teambuilding, planning, and working through tough problems that we just couldn’t land digitally. Recently, I hosted my team in San Francisco. We worked hard, we were vulnerable with each other, and we agreed on methods of working better together. Then we hopped on a boat with a local historian to learn about the Bay. Our data shows that after these gatherings, our employees consistently report an increase in trust, belonging, engagement, and productivity.

Remote work allows you to hire anyone, from anywhere

They say that talent is equally distributed, but opportunity is not. With remote work, you no longer need to hire the best candidate in your city. You can hire the best candidate in the world. It’s hard to articulate what a game changer this is. Now, you can access a global talent pool more diverse than you ever imagined, with people from all backgrounds, demographics, and skills.

Another interesting aspect of remote work is that it allows you to hire, and bring out the best in, employees who may not have thrived in a traditional office environment. Some people write amazing code quietly from their own timezone. Others jam together in a space full of buzz and noise. And some lean into communication channels like Slack or email to share trust-building updates. Digital workspaces often enable employees from a range of backgrounds to shine in a way that loud, busy offices never could.

Build culture with intentional, thoughtful design

When building a remote culture, it’s important to deeply consider the tools, rituals, and growth opportunities your employees need.

Showing up to virtual meetings with a good tech setup is the digital equivalent to arriving at an in-person meeting on time. Lags and glitches can reduce productivity, so we make sure all employees are on an equal playing field with their office setup. Employees now receive an Apple M1 laptop and essentials like microphones, webcams, standing desks, and ergonomic chairs.

We’ve set up and maintained important rituals, like our weekly Town Hall where we gather digitally as a global team to learn about important topics, and an internal podcast that gives context on key decisions throughout the company’s history.

And there’s never been a more critical time to invest in an employee’s career growth. The Great Resignation isn’t about people leaving the workforce—it’s about people leaving their current employer for better opportunities. These days, people seek workplaces that support their career advancement and personal wellbeing, and it’s up to organizations to continually prove that their employees are in the right place. Some of the ways we do this include dedicated internal movement teams, in-house coaching and mentorship, and encouraging employees to expense things that help them learn, whether it’s a conference, course, book, or tool.

Each company will require their own programs for success, but be sure to rethink everything you built for the office days. We need to be innovative now, not iterative. We need entirely new tools, systems, and technologies.

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It’s early days for our Digital by Design experiment. We haven’t figured it all out. We’re going to screw some things up, and we’re also going to do some great things. 

Above all, I leave you with this: if your organization is able to work remotely, do it. Great culture and productivity have nothing to do with where office walls are located. Give your team the chance to build their lives on their own terms, and grant yourself access to the broadest, most diverse talent pool on the planet. Don’t just dip your toe in with a hybrid model. Go all in. Decentralize job opportunities. Focus on mission, not office. Prioritize people, not place. This is the future of work. 

Michael Merola is vice president of employee experience at Shopify, an e-commerce platform. He’s a former director of workplace-workforce at Airbnb.