Work, work, work, work, work, work

Work, work, work, work, work, work

Hey friends,

I don’t often talk about my work. But I figured as I step into a new role I thought it would be a good time to reflect on my personal journey through the jungle gym we call a career. 



Let’s start by going back in time. The year was 2012 - I was designing a clothing line that’s primary focus was on making quality products in Canada. When it came to needing an ecommerce solution I chose Shopify as they were a Canadian company that most closely matched the ethos of my brand. When I was looking at opening up a retail shop Shopify had recently added their POS product to their platform and the choice was again a natural one. 

Fast forward to 2014 - The store was really struggling. My dreams of having my clothing shop provide my main source of income had long passed. I was living off the gratitude of friends and family. Spending a few weeks, a month, at different locations. My fixed address was the store that was struggling more and more to make the various payments we were on the hook for. I had a friend who worked at Shopify and encouraged me to give an application a shot. 

I remember my interview for Shopify - it was at 8:30am PST - I did that interview from the same couch I slept on the night before. I remember being excited for the opportunity. I remember getting the call that I got the job - I remember the sense of pride I felt that day. A feeling that maybe this time life might just get a little bit easier… 

 My first day at Shopify was one that is still fresh in my mind. I was in a training group with people across Canada. It started at 8:30am...eastern standard time. My laptop had yet to be delivered and I was using the store as my primary address so that day I had to get up at 4:30am to ride my bike to the shop to start work and await my new computer that day. It was early November and the road was dark and cold. A light fog and breaking morning light guided me towards the shop that day. I knew I was on some type of journey. 

My first year at Shopify was a hectic one. I would work at the shop from 10am-3:30pm Monday to Saturday. And then work at Shopify from 4pm-12am five days a week on a rotating schedule. After twelve months of burning the candle pretty hard from both ends. I made the decision to close up the shop and focus on my work at Shopify. 


With my new laser focus on working at Shopify I was able to move from the support advisor position into one that had a focus on hiring and mentoring new employees. I loved working with the new employees - doing what I could to tell my personal story using Shopify and how important it is to help anyone who takes the time to reach out to Shopify. I became the lead of the mentoring/ hiring team. This really was the first time in life that I was a true manager. Although we had some employees at the store we didn't really have anyone who was full or even part time. This brought on new learnings and challenges. I even wrote a really fun blog post on what it's like designing and implementing a hiring process which you can read [here].

Now nothing against my friends working in HR - but I never saw myself as someone with a passion for hiring or human resources in general. I did enjoy the side that was designing systems for humans to use and interact with. I was able to learn so much about hiring and i'm sure these skills will serve me well into the future. I ended up leading a hiring team of 10 people in 5 time zones and 3 countries. Me and my team have always been remote so we were already on the knife edge that was hiring, and working from home. 

The pandemic has really provided such an amazing reflection point of what really matters. But it gave me sometime to reflect on what really matters both in life and at work. I have always loved working at Shopify - I feel like I have been on some sort of moral mission - doing work that is so much bigger than myself. Knowing that people just like me are able to realize their dreams. That we can provide a future or some stability to creatives and businesses just trying to do what their heart desires. 

And it is this desire that I reflected on myself. I found myself working in hiring getting deeper and deeper into the HR org that wasn’t my heart. It was only a few weeks ago that one of my work friends reached out. Saying hey you should check out this posting on the internal job board. I of course complained saying that I didn't have an application ready, I wasn't sure if it was the right role for me right now. My friend made it pretty simple - iain you are retail. 

I consulted one of my other work friends who instead of questioning my motives literally opened a fresh google doc and started building my new CV and cover letter. My friends became my champions. I had their hands reaching out and elevating me to a new level. They know the context and my work ethic even better than I do. They understood my ability to take on a challenge better than even I did. 

I submitted my application on a Thursday - Friday I was greeted with an interview request for Monday. After that interview I was welcomed to complete a case study to present on Thursday. In the words of Shopify’s first CFO Russ - “Creativity comes when constraints are applied”. The case study was very much a look at what the role would be like. I enjoyed the process so much and then was left in the space of being really excited about an opportunity and waiting to find out the next steps. I also have the misfortune of working in hiring and knowing anyone I would be up against would most likely be someone my team hired. And I like to think I'm good at my job 🤣. But thankfully all the hard work over the years paid off. I was offered the new role as a Retail Launch Engineer. 

It feels like my journey has come around full circle - Once again I will be trying to figure out how to implement Shopify within a retail context. The excitement of dreams coming together. My six plus years of Shopify context and fifteen years of retail work combined. The idea that a guy who failed out of high school and ran an unsuccessful retail store and fashion line can still make it. A reminder that if you focus on having fun and working hard it can come together. 

-iain