The New Job: Technical Evangelist at Shopify

All right, enough hinting. Time to lay all the cards on the table.

Some of you guessed, intuited or ratiocinated correctly: I am going to work at Shopify. My role will be something that I’ve been refining for the past 10 years — both formally at OpenCola, then Tucows and finally Microsoft, and informally with the Peekabooty project, DemoCamp Toronto, b5media and Toronto’s worst-run startup – the role of Technical Evangelist. We haven’t worked on my exact title, but there’s time aplenty to figure it out.

The Shopify Story

Shopify is the best platform out there for creating online stores. It was created by software developer Tobias “Tobi” Lütke (hint #9 from my series of image hints, pictured above), whose contributions to the world of software include his stint on the Ruby on Rails core team, the Active Merchant library, the Typo blogging engine and the Liquid templating language.

Shopify was created when Tobi co-founded Snow Devil, an online store for snowboarding equipment. When he couldn’t find a decent online store package, he used his programming skills – my friend Pete Forde waxes poetic about Tobi’s ability to code – and wrote his own. The resulting store was simple, smart and elegant, and Tobi realized that he shouldn’t be selling snowboards, but stores.

Shopify have been doing quite well. Here’s a snapshot of their performance last year:

• Shopify hosted over 11,000 online stores (a 70% increase over 2009)
• With a total of over 2.7 million customers (more than double the sales in 2009)
• Who placed over 1.6 million orders (a 132% increase over 2009)
• Which would result in $124 million in sales
• And they provided 22,000 phone support minutes

They also teamed up with Tim “The Four-Hour Work Week” Ferriss to launch the Build-a-Business Contest, which offered a $100,000 grand prize to the new Shopify-based business that posted the highest-grossing sales during the contest period. The end result: almost 1,400 new businesses making over $3.5 million in revenue with nearly 67,000 orders. The winning business was DODOcase, who make gorgeous book-like protective cases for tablets such as the iPad 2, iPad, Playbook and Kindle. Ferriss also acts as an advisor to Shopify.

Shopify have been profitable on their own, but they’re also ambitious. That’s why they secured $7 million in Series A funding from Bessemer Venture Partners, FirstMark Capital and Felicis Ventures in December. Their plan for the “seven large”? To invest it in product development, infrastructure, tools and technology, international expansion and getting their paws on the best damn tech evangelist they can find.

And that’s where I come in.

The Evangelist Story

I got to know some of the people from Shopify at conferences like RubyFringe, FutureRuby and CUSEC and have become friends with a number of them. Since getting funding, they’ve been looking for developer evangelists and called on me to give them some pointers on whom to look for and where to look.

“It’s like hunting unicorns!” said Shopify’s Edward Ocampo-Gooding of the task of looking for evangelists, and he’s right. The job requires a rare mix of technical chops, people skills, writing savvy, presentation mojo and business sense. Edward asked me for some help in February, and I came up with a list of skills sets, personality types, indicators and place to look and emailed it to him, thinking that that would be the limit of my involvement with their search.

A couple of weeks later, Tobi contacted me with a straight-to-the-point message: What are your plans?

“The startup scene is missing you dearly,” he said, “and we have a position here that would fit you like a glove.”

If you asked me six months ago what my career plans were, they’d have been to stay at Microsoft for a good while longer. The company’s been making a number of right moves, I’d been assigned to the challenging role of promoting Windows Phone, I was the Supreme Kahuna of the developer tracks at Microsoft Canada’s big cross-country tech conference, and I was also Microsoft Canada’s most prolific blogger. I worked not in a cubicle, but in my home office, Hacklab or a number of cafes, got assigned enough gear to fill my Honda CR-V and made enough coin to become part of the Toronto Life demographic.

But as I have learned firsthand, a lot can change in six months. From getting separated to nearly getting dead and a whole host of other things best left unblogged (meet up with me in person, buy me a stiff drink or two and I’ll spin a good yarn for you), the universe seems to have seen fit to shake things up for me. So I decided to respond in kind and shake it back.

I went back and forth over their invitation for about a month. The Golden Handcuffs have a powerful grip, but in the end, I decided to follow my own advice and choose the path that I believed was truer to me.

“Let me get this straight,” I told them. “You’re offering a pay cut, risk and total disruption…

Where do I sign up?”

Introducing “Alternate Accordion City”

One interesting wrinkle is that Shopify isn’t in Accordion City. It’s in Ottawa.

“Would I have to move to Ottawa?” I asked Tobi and Shopify’s Chief Platform Officer, Harley Finkelstein. Ottawa’s a beautiful city with plenty to recommend it, but the Canadian cities in which I’d prefer to live are the “MTV” ones: Montreal, Toronto and Vancouver.

“Actually, for the evangelist position, you might be better off working out of Toronto,” they said, much to my relief. “It’s the big business city, and better for flying to the States, which you’ll be doing a lot.”

“But…” added Tobi, “we’d like it if you could spend your first couple of months in Ottawa. You know, to get immersed in Shopify, learn our tech, get to know us and for us to get to know you. Besides, Ottawa’s nice in the summer.”

I thought it over and realized, hey, nothing’s really holding me back. When am I going to have this degree of freedom and mobility in my life again?

“Okay, you have a deal,” I said. “I figure I should hang onto my current lease, but I can’t pay two rents at the same time. Find me a place in Ottawa, and you’ve got me on the premises for the summer.”

If you walk into Shopify’s offices, the first person you’ll meet is Brittany Forsyth, one of their HR people, and she’s stationed at the front desk. She landed me a place at 126 Sparks, which is practically crawling distance from Shopify, and damn, is the place pretty sweet.

Shopify’s offices are in ByWard Market, which is Ottawa’s most lively neighbourhood, as it’s home to a number of bars and restaurants. Between the apartment and the office, there should be enough goings-on to keep a fella like me amused:

Click the photo above to see it at full size.

One week from today, I’m going to pack what I need to live away from home for four months into my car, crank up the tunes, point the wheel towards Highway 401 and make my way to Ottawa for the summer.

After the summer, Toronto will be my home base, although I expect that I’ll be making regular visits to Ottawa. Thankfully, Porter Airlines and the Toronto Island Airport make this fairly easy.

Travellin’ Man

Although Shopify is a Canadian company, most of its customers are not in Canada. They’re in the United States, so a good chunk of the job involves travel there. I’m going to have to step up my plans to get a Nexus pass.

The 2011 BarCamp Tour will be the first of my series of trips to the U.S.. The BarCamp Tour is a tour of various BarCamps by five startups – Batchbook, Grasshopper, MailChimp, Wufoo and Shopify – who provide sponsorship and promotion, assistance to organizers and enthusiastic participation at BarCamps across North America. The first city was Boston, and next up, on May 7th is Minneapolis. After that are Portlandia (May 20 – 21) and Seattle (June 24 – 25).

“The Valley” is still where a lot of the online action is, and it’s expected that I will be making regular trips there. It has been hinted that I may have some extended stays in the area, which may require a pied-a-terre, a home-away-from-home down there where I can crash. I’m not complaining one bit.

The Adventure Begins Anew

And so here I am, putting the finishing touches on this blog entry. As I write this, it’s Monday, April 25th at 12:58 a.m., and I’m sitting in my darkened home office, bathed in the glow of a large LCD monitor and the sounds of Groove Salad coming from my speakers.

I’m on vacation, so my original plan was to hold off on writing this until the morning. However, restlessness, excitement, anxiousness and the exhilarating uncertainty of this next chapter have conspired to set me in front of the keyboard and write. This is only the beginning of a lot of changes, some interesting experiences and what I’m certain will turn into a helluva lot of stories. It’s going to be an adventure, and on this blog, I plan to take you along for the ride.

See you out there!

This article also appears in Global Nerdy.