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Talking with Daniel Debow, VP at Shopify, on the modern workplace and leadership

With online retail and e-commerce platforms skyrocketing in our modern workplace, Shopify has mastered the art of empowering entrepreneurs and making e-commerce accessible to everyone.

In this episode, Joe talks with Daniel Debow, Vice President of Marketing at Shopify, to discuss the future of the modern workplace, how remote-working has changed the hiring race, and managing work-life balance.

Entrepreneurial Beginnings

An entrepreneur from Toronto, Daniel considered himself lucky to be offered a job at a startup right out of business and law school. That company grew and eventually went public, and after being sold to enterprise software company Infor, he decided he was ready for his next startup challenge.

He went on to found Rypple, a cloud computing-based social performance management platform, which was a successful venture that grew and was eventually sold to Salesforce, where Daniel would continue working for several more years.

After that, he found Helpful with cofounder Farhan Thawar, which would be acquired by Shopify, where they are now both VPs.

Throughout this whole process he did a lot of early-stage angel investing. He is now teaching a course at the University of Toronto Law school, and in his free time considers himself a pretty avid musician.

Shopify

For those who don’t know, Shopify is an eCommerce platform and retail operating system with over one million merchants worldwide. Currently, they are working with some of the biggest online direct-to-consumer merchants out there, but are also collaborating with small businesses in your neighborhood.

The mission of Shopify is about “empowering entrepreneurs and making commerce better for everybody.”

In addition to the company’s wild success and phenomenal product offerings, Daniel says it’s just an all-around pretty amazing place to work. And that starts with leadership and culture.

Coming from an entrepreneurial background, Daniel is excited about Shopify’s ability to maintain that entrepreneurial spirit, even at its current (obviously much larger) size. That’s not the norm for larger companies.

The Modern Workplace

Daniel starts off this topic with a caveat that “there’s no one right way to run a business, run a culture, or define the future of work.” Too often we all probably have a one-size-fits-all-approach as to how we frame a company, and that’s not always accurate. There will be many different “futures of work.”

To understand the future of work, one of the best ways to make predictions is to “look at what the kids are doing.” Most of Daniel’s insights for Rypple came from analyzing how millennials utilized different tools of communication while they were growing up, mainly being social media. This was the impetus to figuring out the UX for Rypple, essentially taking a functional recreational experience from Facebook and applying it to a professional feedback tool.

This resonated well with companies that had progressive, young workforces.

Taking this mindset and applying it to trends of today, Daniel is confident that the future of work involves a lot of live and asynchronous video in ways we’ve never thought about using before. It will also become a less formal and far more authentic means of communication, more like a normal in-person conversation with coworkers.

Real estate is also going to see a major shift, with more and more offices realizing just how much can be accomplished remotely and how much better the quality of life can be for non-commuting employees. In its place, there’s going to be significant resources invested into making our remote-working tools a lot better.

Lastly, is in AR/VR. Daniel is currently investing a lot in the virtual reality space for work. The immediate rush to remote work has significantly sped up a lot of businesses’ interest in this sort of experience and technology for their employees.

One of the most dramatic changes in the immediate (and for many companies, unprepared) move to remote work will not be in the adoption of tools or a change in style, but more along the lines of changing the entire mindset in which they make decisions. This whole experience, in a way, might have been empowering for a lot of companies who can look at how they’ve successfully accomplished moving a large workforce entirely into their own homes, and applying that past experience into confidence when making other future decisions. It should raise all of our expectations. We now know businesses are capable of making big decisions extremely quickly when they want to.

Removing Duality

Until now, there has always been this clear division between one’s professional and one’s home life. A lot of that barrier has been removed with most people now working from home. Daniel thinks this is a positive change.

The de-mystifying of one’s personal life seems like an overall far less exhausting way to live and improvement in overall quality of life. Many people for years have operated under (sometimes) entirely different personas. One version of a person turns on when they walk through the door of an office and an entirely different version might exist when entering the front door of their own home.

Joe mentions that for his team, he likes encouraging the “one-take” approach when filming a video. If a kid happens to run through the background or a dog barks that’s completely fine. Removing the stigma around the reality of home life creates a more authentic work environment and increased productivity. Daniel mentions that he enjoys when his kids come into a Zoom meeting as it can relax the vibe of the tenure.

Self-Reflection

Everyone always has room for improvement when it comes to leadership and interpersonal skills.

Daniel feels that this entire Covid experience has done a lot for improving his patience and taking the time to check in with people, as in seriously checking in with how they are doing and letting them know he cares.

Genuinely caring for the well-being of colleagues and addressing their needs early on allows everyone to work more effectively later on.

Listen to the episode here.

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