From A Remote Company to a Remote Role.

I’ve heard this question at least 10 times in my first month at Shopify. “So you work for Shopify in London? Where is your office based?”

For whatever reason that line of conversation generally spins into a discussion of what it’s like to work remotely for a company with a strong office culture. It’s a conversation I genuinely enjoy having but the truth is I am still figuring out how to answer it. Literally on a daily basis I’m trying to navigate the feels and dynamics. People that know me well, know that I love being around people. I am the king of FOMO. People are genuinely interesting. I’m that annoying Uber passenger that wants to know your life story on the way to the airport. The Airbnb host that invites you out to dinner. People that know me well worry about me when it comes to remote working. “Joel are you okay working by yourself out there in big old bad London?” Yes, I am. So let’s start there.

Why I love remote working?

The Commute

I’m from LA. We know all about the commute and whilst I’ve lived abroad in much smaller cities (Cape Town) I’ve dealt with the hustle and bustle of traffic and having to re-acclimatize myself in an office environment. It’s a huge time suck, distraction and often encourages people to cut out early to beat the traffic, or stay late. Time is money.

Freedom, Flexibility, Focus

We all face our ebbs and flows of energy. We attempt to hit our peak caffeine climax. I firmly believe that If you aren’t productive surely you are better off spending time at the gym, with family, or doing a host of other things that might spark creativity, give you energy or make you feel better. Working remotely caters well for this and it’s become an increasingly popular (or perhaps trendy) way of running a successful businesses. If you’re productive at night — work at night; If you dip in the afternoons — take a nap. Many office cultures can replicate much of this by offering freedom and amenities. But remote working allows one to create their own norm and flow which may differ day to day and can be done free of guilt or weighing your actions against your team face to face. This is not to say that remote companies do not generate their own norms or issues (I’ll save that for another post).

Where do I want to work today?

I can’t be alone for too long. In this regard, I’m spoiled AF in London, where coffee shops cater for remote workers. Take Ace Hotel in Shoreditch for example or Google Campus. Beautiful spaces that embrace this new generation of freelancers and remote workers. This is the opposite of your coffee shops that don’t have power plugs (I won’t name names). I try to schedule my day to have a cluster of calls together that I head home for. I might pop over to a local bar for an evening work session. I’m all over the place, and I like it. It’s a daily quest for good internet and coffee. And the dream of the 2000’s is alive in Shoreditch.

The World is Your Oyster

My wife and I have become that annoying couple that travels a lot. Renting our place on Airbnb makes doing that much much more affordable (blog post forthcoming on this). Check out our travel blog here. Working whilst traveling or temporarily relocating is a huge draw card for remote working. During my time at WooCommerce (later purchased by Automattic) I was able to follow my wife around while she interned at the Museum of Innocence in Istanbul and the Smithsonian in Washington DC. We worked for two weeks from Koh Tao, Thailand where we met a ton of remote workers. Not all remote jobs allow for this wild lifestyle. My new role is focused on Europe so I’ll be much more useful in London but that won’t stop me from working the odd day from [insert destination].

Things I learned while remote working for WooCommerce / Automattic

WooCommerce

When I began at Woo we had an office and worked the odd day from home. As we began to hire more remote employees we decided to improve the experience for our global staff and we changed the way we operated. I was personally opposed. I didn’t want to lose the opportunity to play Fifa and talk people’s ears off. I was fighting a losing battle, though. Once we experimented with fully remote we immediately witnessed a positive change in communication and reliance on transparency. There was no going back. We still had the office and just had to be a bit more strategic in enticing people to come in — usually free lunch did the trick. And when we all came together it was special.

Automattic (best known for WordPress.com)

After being acquired, our team of 50 was thrown into the wild world of Automattic. I think we all spent days if not weeks absorbing the wealth of Slack channel communications and P2 boards. Matt Mullenweg has a saying that I love: “communication is oxygen”. Automattic lived and breathed that mantra because when fully remote you have to. Transparency and communication is literally the means of getting things done and proving your value. It’s not perfect or easy — Figuring out how to work with people remotely without relationship (at least initially) can be difficult. I learned a lot from Automattic. (Here is a great blog post from a former colleague, Alister Scott on communication at Automattic.)

I think transparency and overcoming fear of confrontation and potentially being wrong are so important via online communications. The alternative approach is so dangerous. If you have employees that are afraid to share what they are working on or afraid of disagreeing how can we really do something special? So I want to personally thank Woo and Automattic for teaching me a different way of being. Putting your work on display for ridicule or praise is scary, but so what. Speaking in channels with the CEO and other execs can breed insecurity, but Automattic showed me that it doesn’t have to.

The experience of being remote at a company with an office culture: Shopify, my new home.

I’m really tempted to go into a tailspin discussing how amazing Shopify’s offices are but I’ll restrain myself. In my last blog post I reflected on the on-boarding process of Shopify which was an incredible experience. I left Ottawa, inspired and missing what felt like my new family. Returning to London full of ideas and ambitions, I woke up as usual and opened my laptop. Silence. It didn’t hit me until day 1 of remote working that I am one of just a handful of remote employees at Shopify. Fortunately I have my teammate Shauna out of county Mayo, aka the ‘Irish Hustler’. Shauna, formerly a guru for Shopify, started at the same time as me on the partnerships team. Being able to collaborate with Shauna and a few other awesome UK teammates has been really key.

Where to Start?

There was no perfect road map on how to get started, which I really appreciate. I realize this would scare the shit out of a lot of people. Shopify is all about ‘Getting Shit Done’ whilst encouraging a ‘Founders Mentality’. For us looking at an entire region of partners / stakeholders was and is overwhelming and exciting. Figuring out what we do, what makes an impact, and scaling our efforts will be a constant reiteration. We are given freedom but with that freedom comes an expectation to see results. Our CEO Tobi Lütke has a term: the trust battery. In short, when an employee starts at a new company there is risk on both sides and trust has to be earned. This trust doesn’t start at 0%, getting a job at Shopify isn’t that easy, so surely being hired we’ve already proven something and hopefully that trust grows.

Communication

Within our little team we decided we wanted to be as open as possible with our ideas, communication and plans. We created an open #slack channel, open trello boards with ideas and plans and communicate openly as much as possible. Obviously we want to show the company what we are working on, but our goals for doing this extend beyond recognition. We have a ton to learn from others and welcome their collaboration. We are trying to figure out how things work and how to solve problems. Opening conversation and ideas up to anyone is important for us. Speaking openly is actually quite freeing. When things get sensitive the tendency is to move over to a private message but we’ve tried to avoid speaking in silos. The historical record of what we’ve been up to is there for the taking. The general stance is, we have nothing to hide, nothing to be ashamed of or afraid of.

Reflections thus Far

The idea of open channels is not novel to Shopify but I think our reliance on them (as remotes) to communicate openly is not normal. I had one person mention that because of our sharing style that people are looking at Google Docs (ie: meeting agendas) and they shouldn’t be in there. Which is kind of the point of transparency. People can see everything going on and collaborate, correct and maybe learn.

The Fomo is Real

Not being able to have lunches and moments together is tough only because I’ve had a taste of of an amazing office culture. Knowing how much fun everyone is having makes the heart grow fonder. What could be a subtly pitched idea over lunch can be perceived differently in a slack channel.

Emoticons and Giphy cover an Abundance of Sins

It’s a real challenge to read people online but not a challenge that can’t be overcome by any means. It just takes time and lots of reading between the lines by what is said, not said and reading into reactions. And the reality is that 90% of things you read into negatively, if you are an over-analyzer like me are false realities. One thing I learned at Automattic was to always give reactive, emotional emails a day before I send them. 99.9% of the time I wouldn’t send them, I get over it. It’s amazing how much emoticons and giphy feed the soul, lighten the mood and bring character to otherwise hard to read text.

Balance

Shopify seems to have found or, in some cases, is finding ways to create an amazing balance between remote staff and incredible office culture. Tools and systems are in place to make it easy to quickly jump on calls or be part of sessions happening in Canadian offices. Our specific team recently made the jump from having 20~ people in a boardroom on one video with 10~ tuning in remotely over to Zoom where everyone could be visible and have a bit more of a voice. This is certainly in place to benefit us remotes and it really helps me feel connected.

Silence is Nice

It’s so interesting how big an impact time zones and a company’s geographical composition has on workflow. At Automattic I was constantly engaging with staff in South Africa over Slack and had to be ready at any time to respond. At Shopify the VAST majority of the people I interact with are based in Canada, just a 5 hour time difference away. Honestly, this is kind of amazing. My mornings and afternoons are quieter before Slack lights up at 2pm with a frenzy of activity. I recall working regularly with colleagues in PST from South Africa and later the UK while at Automattic. Bridging multiple time zones to collaborate is a real challenge and should be a major consideration for the composition of remote teams.

Completely Remote vs Office Culture vs Being Remote with a Company with an Office Culture

I’ll start by saying that nothing beats meeting in person to make decisions and accomplish things. Video calls bridge a lot of the in person gaps but it’s still a big gap. So much is lost via virtual calls. Things like body language, spontaneous discussions and all that happens before and after a meeting are easily overlooked. Meetings to have meetings can happen in a remote or office environment but I imagine it’s easier to move to a limited meeting culture via remote teams. Reliance on other means of communication such as Slack, Boards and other tools like Asana / Trello can lead to much more fluid engagements. Ultimately though Slack and other tools can be seen as noise but it all comes down to how it is used. Via remote companies I’d also argue that transparency and flat organizational structures can lead to decision making paralysis. So lots of pros and cons to both structures.

A healthy balance of communication, transparency and usage of tools coupled with actual relationships and feedback seems like the healthiest approach to me. The alternative is a false-autonomy where anything can be done, shared and discussed, but without collaboration and feedback in some form of a hierarchical structure it’s easy to be left paralyzed by fear.

Inspiring the masses

You can feel the buzz as you walk through the Shopify office in Ottawa. In the partnerships pod it’s not uncommon to see Harley (our COO) cruise around and have impromptu conversations about exciting things going on. My second day in the pod I recall him coming in and with his infectious energy saying “the jumping castle’s all set for delivery to Kylie” (context). The inside jokes run rampant, discussions are about projects and what’s on the menu for lunch. It’s not perfect but it’s cohesive and it’s focused. Tours are being given, new employees being shuttled around. It’s an organized, beautiful blend of fun, energy and excitement. Friday afternoons the craft beer and hors d’oeuvres get served up for the weekly town hall. I’ve only seen 3–4 of them but they are filled with product innovation updates, success stories and team updates. All around is inspirational art, mantras and a reminder that you are part of something special.

How the hell do you replicate all that online?

Ya, well you can’t. It’s just too much amazing. I’m not saying it’s impossible to inspire a remote team or company, of course you can. But my point is that special things happen when people come together and coexist in a space. Tangibly they see things happening, growing and evolving. They experience the complex emotions and interminglings of life with others in way that is very hard to experience online. We can’t replicate that experience with remote tools yet. Remote companies can and do compensate for this with annual gatherings and meetups, and because of the in-person relational deficit that’s accrued, these meetings become even more pivotal to remote companies.

Team meetups give you a great excuse to try crazy things :) #scaryassteambuilding

However, remote working is going to become a bigger part of our lives as more companies big and small make coming into the office optional, or do away with a physical office all together. I have my doubts about its ability to scale to large companies but if anyone can do it Automattic can, and I hope they continue to flourish. As for me, I love remote working but know that it comes at a cost. But I’m able to cope with that cost because of the other things it affords me.

At a personal level, different strokes for different folks. To me, an office culture central rocketship with remote tendencies seems ideal but requires mindfulness and investment in cultivating a culture that caters for an environment conducive to remote workers.

Shameless Plug: Remote Jobs at Shopify

If you are interested in joining the rocketship that is Shopify here are current job openings.

Questions or comments, don’t hesitate @joelbronkowski