Day 0 | Unemployed | Leaving Shopify: My Journey Through the World of eCommerce

I’ve decided to leave Shopify after having the privilege of working there for the past two years. I’d like to take a few minutes to reflect on my journey in the world of eCommerce and what it has meant to me.

Let’s go back to a different time, a different place:

It was 2011; I had been living in Cape Town for 4 years. I spent two of these working at a non-profit focused on leadership development in impoverished communities and another two years in grad school studying Sustainable Development. Both of these were a far departure from my life in sales and business in the States. But it’s indicative of my character: I’ve always been an odd blend of humanitarian and capitalist. I love business and was growing increasingly skeptical of my future in the non-profit world. I was nearly broke, but hopelessly in love. I felt the world on my shoulders and knew I had to make something of my life and career in South Africa or I would need to make the move back to the USA. It’s there where I re-ignited my passion for eCommerce and discovered how far the space had come. In one day I built two online stores using WordPress and WooCommerce. I imported $500 worth of Chinese products and spent $50 on ads. Boom. I was in business.

In just a few weeks I was packaging and shipping dozens of shitty knock-off iPhone cables every day. It felt great. In parallel with this I was pursuing job opportunities, and ultimately this store led me to land an interview with WooCommerce in Cape Town (I had no idea they were even based there!). They passed on me at first, but hired me just a few months later.

In a short amount of time I found myself leading Woo’s business development and brokering deals aimed at creating new revenue streams for the company. I had no idea what I was doing and it was intoxicating. I was learning hourly. That role took me so far out of my comfort zone I looked back and didn’t know who I was. I became something. I was a WordPress outsider with little technical knowledge but became somebody in that world. More importantly I developed relationships with an incredible community of people. My world got so much bigger in just a few years. A few years in we were sitting at the table with VCs and the world’s leading eCommerce service providers. We went from being the ‘David’ in David vs Goliath to sitting somewhere amidst the world’s leaders in eCommerce. I was empowered by trust. I couldn’t believe the trust I was given. I developed a confidence that felt unshakable. I developed global bonds with what felt like a family.

In 2015 we were acquired by Automattic. There we were in New York with the CEO — the founder of WordPress — and his team. It was exhilarating and terrifying. My comfort zone was shaken again, but our success in 2015–2016 continued and amidst some real challenges to adapt we continued to grow.

I felt, however, an increasing sense that I had lost something. Looking back on this I think it was that ‘David’ spirit. We had reached a level that required us to get much better and solve much more complex problems. The reality was that I found myself out of depth at times, and instead of humbling myself to these realities I tried to mask my insecurity with false confidence. I reached a point where I felt like Woo wasn’t enjoyable anymore. Something was lost with the acquisition for me. It’s hard to pinpoint it; perhaps it was the trust, perhaps it was the underdog sentiment.

I was ready for something new and while I wasn’t actively looking to move on, other opportunities presented themselves. My eventual departure from Woo was unceremonious, which felt so wrong, given how much it has changed me and all that was endured with my Woo comrades.

It was time to move and there was nowhere else I could see myself going other than Shopify.

Hello Canada

I flew up to Ottawa after WooConf 2016 , (who knew it could be so frigid in May!). It was 9pm following a full day of flying from LA and it was cold, dark and everything was closed. I found a virtual golf bar that had just opened, where I experienced my first Canadian hospitality (the first of much love). Poutine, local beer and great conversation got me pretty pumped on Canada. The next day consisted of a series of candid interviews and a tour of the beautiful Shopify HQ. I knew I got the job.

I was so excited to be the first BD and partnerships guy in Europe. I met my teammate — an incredibly passionate and talented guru in Ireland. We took on the world. What do you do with thousands of partners? We formed relationships like crazy and learned as much as we could in those first few months. In many ways it was easy. We had so many amazing partners doing so much amazing work for Shopify. Our biggest accomplishment was recognizing them, connecting them to each other and building communities to further put Shopify on the map. Our enthusiasm and presence in these markets brought about a palatable difference and paved the way for a ton of positive impact and growth the past few years. We had something to prove and it was simply an honor to represent Shopify to hundreds, perhaps thousands, of people making their livelihoods as Shopify partners.

It’s hard to compare WordPress and Shopify and I won’t try to do so in this post. I will simply say Shopify partners are merchant success obsessed. Meetups and meetings in general are far more focused on helping merchants. There is far less emphasis on the technical. It’s a very, very different ecosystem. Bringing partners together from all over Europe, and later the world, was further proof that relationships are everything; results follow.

Shopify as a whole is obsessed with helping entrepreneurs and merchants. This notion transcends the internal jargon. It’s been incredible to see such speed in improving the platform. It’s near impossible to keep up with it all.

Transitioning to lead an even bigger international team was a challenge and a treat. Operating as a remote team in a company and department that is predominantly in Canada was not easy. But it’s these same challenges that made what we were a part of so special. When we came together for the first time in the summer of 2017 it will go down as one of the highlights of my career. Bringing together such a diverse, passionate group of people and trying to figure out how to be successful was a beautiful moment. The time together transcended your typical offsite highs. I would chalk a lot of this up to diversity of our group and the challenge of connectedness as remote employees and how powerful this time becomes when it happens.

I am incredibly grateful for my time at Shopify. I feel so lucky to have been a small part of the foundation of a growing international effort at Shopify. As an American I feel so lucky to have been privy to this beautiful made-in-Canada story. Canada is a beacon of hope in a pretty mad time in our world. I am so thankful for the many Canadian friends I’ve made! I greatly appreciate the hospitality you’ve always shown me in my trips there (thank you for helping me gain 20lbs).

New Beginnings

On paper, my journey at Shopify has been beyond great. Behind the scenes I’ve struggled.

This year in particular has been a challenge as we’ve attempted to get settled in Berlin and faced a myriad of visa issues. As the year has gone on we’ve realized more and more that the time is right for us to make some big moves. One being that we will be leaving Berlin. Anyone that knows me knows I haven’t put roots down in a while and we feel that the time to do so is coming soon. With these impending roots on the horizon in 2019 we want to take some time to pursue one of our passions: traveling! We’ve managed to bounce all over the globe the past 3 years but doing so while writing papers and working full time jobs is not the same. In parallel with this I’ve basically been born with the entrepreneurial bug and want to pursue several ideas. While traveling I’d love to meet folks selling online, building online stores or service providers building tools for online stores.

Someone once said “it’s all about the people, stupid”. Every meetup, every trade show, every call, every spammy linkedin request, every meeting. Every success, every failure and all the lessons in between. Thank you to my Shopify colleagues. Particularly my team: you are a bunch of wild, crazy and unbelievably talented people and I have no doubt you will succeed! In the words of the wise Mr Bakshi, “if you see a partner manager, give them a hug, they are amazing”. Thank you to Shopify partners! I’ve met the most inspiring people accomplishing big, amazing things with small teams. I’ve learned so much from your passion, drive and unparalleled effort.

It’s been a dream and I’m certain I’m just getting started. This boy from the Californian suburbs, who only knew about one kind of cheese (American) and fought with his sisters to use the phone line to check his eBay auctions, has been at the center of a growing wave of people that are finding their livelihoods by taking leaps of faith — and it’s time for my next jump.

Right now it feels more like a fall; it feels weird leaving a company but not being able to physically say goodbye to people I care about. Someday I’ll get my going away party (Perhaps a drink or two at Unite 2019). For now this declaration of independence will have to do. Feel free to comment or drop me a message and I will reply with a sincere comment reflecting on our journeys together.

Thank you for everything Shopify and Shopifolk. I won’t be too far away and I am as confident as ever that you will continue to help an ever-growing pool of entrepreneurs.

Originally Published on Medium.


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