Checkout. The Shopify Story.

Shannon O'Brien
Shopify HR
Published in
9 min readNov 30, 2016

It was just over a year ago when Konval Matin, Director of Culture for Shopify, laid out the task at hand:

“So, we want you to capture everything that makes Shopify Shopify and find a way to share it with our people in the form of an employee handbook.”

No big deal right? Until then, my experience with employee handbooks had been pretty basic: a list of the organization’s rules and policies, a description of the benefits and perks, some pics of people working and having fun — that was about it. How hard could it be to do this for Shopify?

Pretty hard, it turns out, but so worth it. And it started with throwing out all of the above thinking and focusing on the why.

The why.

The first step was to define our high-level goals which were to:

  • Give new hires a strong sense of our culture, and show them how they can succeed at Shopify.
  • Realign our current employees with our vision and values, and encourage meaningful discussions about our culture.
  • Make something so rich in content and design that people would feel compelled to share it with their network.

With those goals in place, the next hurdle was to tackle the how.

The how.

There were endless ways to approach the project and many strong opinions to consider. To begin, there was much debate over whether to go digital or print. Digital would be easier to scale (important in a fast-growth company), simple to distribute, and fast to update. But it lacked the weight and importance we wanted the messages to hold. On the flip side, print, while bringing the burdens of cost and potential for quick stagnation, holds the power of a tactile “unboxing” experience. It also gives a sense that the words within are so important that we felt compelled to commit to them in a more permanent way.

I remember early conversations with our lead culture designer, Mandira Midha, and Daniel Weinand, our Chief Design Officer, about our vision for the project. We were in sync early on (a strong content and design vision alignment? Such a gift!) and we semi-fantasized about what a win would look like. I thought of it as the coffee table scenario. We wanted to create something so visually and contextually interesting that people would leave it on their coffee table when their friends or family came by for a visit. It was one of the few tangible pieces of our culture, and we to create something memorable.

The words.

When it came to content I cast a huge net, capturing every type of content category possible. That was the easy part. The challenge was eliminating the things that would quickly change, making the book obsolete even before it left the presses. For example, our perks and benefits change frequently as the needs of our people and company evolve. So rather than listing each item individually, we chose instead to describe our high-level philosophy and thinking in this area. Layered onto this we also had to consider every role (remote and in-office), every level (leads, directors, individual contributors), every tenure (brand new and long-time employees), and multiple geographies to make sure the content would resonate and be applicable.

It’s not an employee handbook.

During this process, we realized we needed to shrug off the term employee handbook. This quote from our book explains:

“We chose not to call this the Shopify employee handbook as that conjures up thoughts of rules and policies, and that’s really not what we’re about. Instead, consider this book to be an ‘old wise owl’ filled with sage advice for when you want to better understand how we work and how you can succeed here.”

And so, Checkout. The Shopify Story was born.

I wanted the language to be crisp, concise and simple. This, too, was inspired by the “coffee table book” vision. My goal wasn’t to have everyone read the book cover to cover in one sitting. I thought it would be a better experience for someone to pick the book up, open to any page, read a passage, and set it down again. Let the words really sink in. And then later, return to the book and absorb another section. Approaching the writing like this helped keep most sections tight.* It also led to the decision to exclude both a table of contents and page numbers, which are signals to the reader that there is a distinct order in which to read the content. Since learning and experiences at Shopify don’t always operate in a sequential manner, it didn’t make sense to build that into the book.

We wanted to bring a variety of voices into the content, as Shopify’s story is everyone’s to tell. We met with and interviewed a bunch of employees to get different perspectives. We also did an open-call for people to submit definitions for the “Fact and Folklore” section of the book. The original intent was to help new hires learn our language. But recently someone in an R&D role said he enjoyed reading through some of the terms specific to our Support team, as it helped him better understand that team. So that cross-departmental learning is a neat, unexpected outcome.

The other way I brought different voices into Checkout was through storytelling. While a passage about our approach to failure, for instance, is good learning for every employee, a story in the words of someone who’s gone through a personal experience detailing what they learned about themselves and Shopify brings so much more power to that material.

Challenges in the writing process can be summed up with one question: when is a book actually “done”? There was a point where it felt like I could have tweaked, refined, edited, rewrote, and revised Checkout until the end of time. So ultimately (and I credit Konval for this) we just set a deadline and made a commitment to ourselves to “ship it.”

so many edits!

The design

With the words in place, Mandira and fellow culture designer Rachel Lin got to work. In an ideal world, designers would have ample time to play around with 100% final content. In our reality, this wasn’t the case. We’d had too many false starts.

Since they knew the book’s content was high-level, and that we planned to make content updates only once a year, they wanted to keep the design scalable and simple as well. But as we explain in Checkout, simple doesn’t mean simplistic. In other words, the design team also started with a wide net. In their words, “we had to try every other over-complicated idea we had first before we could pare it down. Ultimately, we didn’t want the design or art direction to take away or distract readers from the most important part — the content.”

But time was tight. The printer was booked. And a totally cheesy infomercial video to announce the book at Town Hall was in the works. It was at that point that Mandira and Rachel went into hiding. They sequestered themselves into a small meeting room that became their Checkout basecamp and no one saw them for three weeks.

In order to meet their deadline, they knew their best bet was to create as many design parameters as they could. To help, they limited themselves to a simple art direction: two ink colors, two fonts, one paper stock, and one illustration style. With these in place, they stretched their creative muscles to maximize what they had to work with. For example, they used full-bleed black ink on white stock to fake a black paper stock rather than introducing another one.

Another example of how they made the best use of time was in designing the cover. While the adage may advise otherwise, who doesn’t (at least sometimes) judge a book by it’s cover? The designers allotted a single day for cover design in their strict timeline, and challenged themselves to take one hour, each designing as many covers as they could. At the end of the hour (which ended up closer to two), they shared almost 30 options. The strongest concept emerged fairly quickly because it was both bold and simple.

In step with Shopify’s value of building for the long term, the design incorporated as much white space as possible so future content updates could flow in with flexibility.

When it came to design there were some challenges getting this book off the ground:

  • Because the content was in flux, the designers had to start working on art direction without copy to play around with. This made it difficult to plan different treatments for different types of content.
  • The designers went through a few failed art directions before nailing it. One concept, for example, used a much more saturated and diverse colour palette. But after meeting with the print shop and learning how expensive and labour intensive it would be to incorporate multiple print processes (i.e. multiple paper stocks, foils/metallic inks, letterpress, etc.) to bring the concept to life, they revised the concept for the art direction late in the process.
hot off the press!
  • The designers also wanted the employee stories to stand out by using cut-back pages, which was initially a challenge for the print shop. And while it worked out, it meant we weren’t able to do a planned neon edging around the book, which was a bit disappointing to our vision of the final product.
a closer look at the cut-back pages

Distribution

Once Checkout was at the print shop our next challenge was working with our culture specialists to figure out how we would distribute the book.

At first, we wanted to send each of our newest hires a copy of the book by mail. We quickly realized that was unnecessarily complicated — especially because we didn’t have their home address. So we emailed them a link to a Shopify store where they could order a copy of Checkout to their home before they joined us officially. This gave new hires the experience of using a Shopify store right from the beginning, without us adding complexity to our hiring process. Win win.

But the real challenge was getting the book in the hands of our current employees. First, we’d have to explain why they were getting the book, and second we’d have to hand it out at five different locations and to our remote workers all at the same time.

In the end, we decided to launch the book at a Town Hall meeting (which is live streamed to all employees). We aired an over the top, tongue in cheek infomercial that outlined the benefits of Checkout and what employees could learn from it. It got a lot of laughs. After the video, we handed the books out in the offices and we sent our remote employees a link to that same online store so they could order their copy at the same time.

The evolution of Checkout

Since this book needs to reflect the true Shopify experience we welcome feedback from our employees. We want to make this book better every year to make sure that it remains relevant as our company culture grows and evolves. We’ve already gotten some valuable feedback on both content and design that we plan to integrate into the 2017 version. Feedback is a gift, after all.

As for the “coffee-table book success scenario” Mandira and I daydreamed about months ago? Shortly after we gave it out we heard from an employee, “I have it on my coffee table and my friends have been reading it. Some people are loving the design; other people love the content so much they are taking the advice and applying it to their life.”

I think we’ll call that a success.

* and some kick-ass copy editing by Gillian Massel helped keep the copy crisp and clean

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Shannon O'Brien
Shopify HR

Mama of two, sommelier student, coffee lover. Internal Communications Lead at Shopify.