Shawn Roos About Nowaday Fateful Decision: Remote-First or Remoteish?

15 min readFeb 12, 2020

Shawn Roos is the Product Director at Over, an American company, with offices in Cape Town and London, and 104 employees dotted around the globe. Over is perhaps one of the earliest iOS photo editing apps, which is utilized by millions of users to create designs for business and personal purposes.

At our Remote-First Conference, Shawn talked about finding the balance in the hybrid model that a lot of us find ourselves working, where you find the interplay between the office and remote employees. Using the example of his company, Shawn clearly explained why it is so important to move away from the idea of, “Are you in the office?” and what all that has to do with Churchill and Drake.

All we had to do was transcribe his insightful presentation for our readers.

Before I got into products, I was actually in advertising, was working as a writer specifically and I got really interested in digital work, then started my own digital marketing agency very quickly. I started really enjoying the work where we were building things and we found ourselves building tools to solve problems instead of doing marketing sites. And that kind of led into this journey into products, where I’ve been working either as a product design spec, product strategy spec or product management spec for almost a decade now.

Currently, I’m the director of product at Over. And I’ve been remoteish for quite some time now. So the topic that I’m talking about is something that I’ve definitely experienced in a few companies, in a few different types of them. I’ve done this in a business I owned that was a digital product agency, I’ve done this in a financial services company for a large insurer in Africa. And we’ve been doing this at Over since the beginning.

At Over, which is where I’ve been for the last year (and where I’ve worked previously before as well), we build simple tools to help people build their brand, since 2012. We were really early into the space of mobile design, and while we are a US company, we have offices in both the UK and South Africa. We also have a large number of remote workers, who are scattered across Europe, India, we have Americans working from America, Americans working from South Africa. So a lot of what I’m sharing will be a combination of my life experience and our experience at Over.

I think it would be fair to say that at the moment the world is remote curious. Although I saw a tweet this morning that said only 3 percent of America’s workforce is actually working remotely. Despite that, 67% of U.S. companies are actually working remote or have implemented remote working in some kind of way, shape or form. That was a 2018 Upwork’s study, so it’s likely more by now.

But when we actually dig in a little deeper and look at what that is, we find some of the types of remote work, which is satellite workers, where there’s a large contingent of people working on-site, but with scattered workers who are often the minority. Some companies have implemented remote days like or remote optionality — that is, if you feel like working remote, you can work remote, but generally the expectation is that you work at the office. Other companies are a little bit more ambiguous, they call themselves “remote-friendly”. At Over we also talk about ourselves as being remote-friendly and we’ve been trying to figure this out for ourselves.

Actually, most companies that would call themselves remote are just remoteish. They’re sort of remote. Out of all of the companies that call themselves remote only 31% are fully-remote companies. The largest of these tend to be young companies, and tend to also have young co-founders– they’re early stages. And what’s really interesting is that there’s been some real successes with these types of companies, but for the other 69% of us, the “office factor” is real.

Many remote companies are still headquartered on the ground somewhere, physically located somewhere and not so much in the cloud. What happens is that remote working becomes a way of working, however, the office is at the center, and if you work remotely, you’re kind of scattered — you’re outside of that. And it’s very difficult to know what’s happening in the office, difficult to access that. This creates a situation where remote working is kind of a perk, but if you want to be close to the action, if you want to know what’s happening, you need to be at the office.

That means that remoteish type of work is hard. It’s really hard to find the balance between that: catering and supporting remote work, but also creating a vibrant office space and having the best of both worlds.

Interestingly enough that the Buffer State of Remote spoke about 80% of people who work remotely get absolutely no financial support to do so. You come into the office and there are all kinds of things that we take for granted. And yet, if you choose to work remotely, you get no support whatsoever from the company. f you look at how these companies work operationally, they’re actually functionally indistinct from companies who don’t do remote work. That’s really tough.

In a recent poll conducted by FYI, 27% of the people who responded spoke about communication being difficult, spoke about having lack of access to social opportunities, complained about loneliness and isolation. A lot of problems had to do with the human experience of being remote. And so what’s happened is that a lot of these offices have gone and put technology in place, but that’s all they’ve done — subscribe to a couple of apps.

When you think about this hybrid model: having both fully remote people as well as having people who are co-located, you have to look at the why behind offices. So if you will indulge me for a moment, there is a lot of value to having a physical location in whichever city or country that you find yourself operating and it’s important to understand the value of this. If you are a leader, you want to try get the best of both worlds.

You can’t deny the fact that humans have a connection to physical places. And if you think about the effort that we put into creating office spaces, that are special and conducive to work, then it’s no wonder that people enjoy being there. That’s a real factor.

Offices are also communication superhighways, and i’m not only referring to chatting at the Water Cooler and that kind of thing. I’m talking about just being in the presence of other people. So much communication happens at offices without saying anything. You can go into an office and put your head down and just work solid eight hours and you might not be aware of it, but you’ve learned so much, you’ve spoken so much with other people just by your interactions.

For instance, sometimes I’ll look up and see the marketing team is definitely having a bad day. I haven’t spoken to anyone, but that’s just the reality.

There’s strategic value in offices too. You might find that it’s really important as a business strategy to actually be physically located in a space. That’s definitely been true of Over where we wanted to be able to have meetups and invite people into our space and create a space for creative people in Cape Town. We’ve only just really started in London, but we could definitely see that is being something important into the future there too.

Offices are kind of embodiments of our culture, our values. And this also can’t be understated. You walk into a place and it speaks to you, tells you something about the company you work in. I mean, there’s a lot of reasons why it’s great to have offices.

That’s not to say you have to have offices, but there is also great value to them. This is something I’ve thought a lot about in having worked in so many different companies. Sometimes I’ve been in the situation of working in a place that’s already been designed and other times I’ve started up new businesses and been a part of designing spaces.

There’s the quote by Winston Churchill: “We shape our buildings and thereafter they shape us.” and this is something that we don’t think enough of. Offices codify a culture.

In a lot of companies we don’t have the time, or sometimes actually have the people to really think deeply and articulate what our working culture is, that is, what are the agreements around how we work? The point here is that the physical spaces and the way they’re designed and how things work in those spaces become our culture.

So you have this incidental culture that you didn’t necessarily plan, and that culture is the product of decades of social engineering. Think about meeting rooms, about watercooler moments, cafes — offices are heavily biased towards oral communication. This idea of oral tradition where you want to know something, ask “Jan” or speak to “Pete”, where information and stories of passed down — sort of like early society, and very little is written, it’s always about speaking to people.

Offices are biased towards creating sort of a pedestrian culture. You just walk around the office, go to your meeting, have these routines of places and based on how you move within an office, you learn things.

So especially in early-stage startups, your office culture can become your culture, whether or not you’ve intended it to be or not.

Now, if we go back and look at those remote pains people spoke of again, you’ll realize that you won’t ever really have these in an office, because you can always self organise and talk.

If that’s the case, your office space is simply a band-aid for the fact that you have no functional culture, no explicit working culture. And of course, it’s understandable how remote working breaks down.

So that’s quite a negative outlook, but can being remoteish work? No, I don’t think it can. As long as you work this way, your remote team members are always going to feel like second class citizens.

But if you adopt the principles of being remote-first, then your remote workers and colacated workers will be happy. What that means is that you can’t continue to be implicitly remote as in, “Yes, it’s a perk. You can do it. It’s fine.” You need to become more explicitly remote, so move from remote as a perk to the office as a perk, from remote being a thing that people can do to defaulting to remote.

What we found is that when we are biased towards remote-first principles, people who are co-located tend to love the fact that they get to have more clarity, that they don’t have to be in as many meetings, that it’s okay to just not be available. We found that the more we have started being remote-first, the better the office environment has been.

What’s important to understand here is that we’re not saying that office workers are second class citizens either. There’s this idea about the difference between equality and equity. If you do a Google image search and you type equality versus equity, you’ll see a couple of little cartoon diagrams that explain it really well.

Equality is that regardless of your strengths, everyone gets the same amount of support. Equity is that you understand that certain things need more support than others just because they’re harder to make work.

So actually remote first principles are largely about contracts and agreements, so it needs to be prioritized if it’s going to be able to compete with just culture that emerges out of offices.

And the reason that you want to do this. is that you want to create a single shared, work environment and experience for working. Because it’s impossible to bring everyone into the office, you bring everyone into the cloud and create the shared experience there.

If you want to go to the office — awesome, but you don’t have to, you can have a great experience working and feel like you aren’t missing out on anything.

Think about your office as a technology stack. Offices can either speak to our culture or enhance our working culture. Offices and the spaces in them are actually an interface. They’re designed for jobs to be done.

So, how do you take a look at your office space and go, “What are the things about our office space that work really well for us and how can bring that, create some kind of equivalent in the cloud?”

Some of these things you can’t do. And actually some of the stuff in the office you shouldn’t try to replicate because it’s bad, but it’s important to just start that way and to think about the fact that all the best parts of your office will have some kind of outcome that they were designed for. What you need to do is think about is, “How do we virtualize the stuff?”

So I’ll share briefly just some of the things we’re currently doing, some that we are starting to do or wanting to do in the near future, because over the last two years we’ve grown significantly and we found that being implicitly remote and letting it happen has been fine for some people, but there are definitely people who have gotten lost in that.

We have an incredible office space and what we’ve realized as we’ve hired more people who are further out and distributed across different time zones is that we actually have to create an incredible virtual experience of working at Over where offices are optional.

So the one thing that’s obvious is that we’re moving from physical to virtual now. One thing we did recently: every single meeting is remote by default. We have a lot of meetings where everyone is actually in the office, but they all do the meeting over Zoom. We’ve moved away from this idea of, “Are you in the office?”

Another thing for us is doing work conferences.

This is a video of our company doing a two-day workshop. We did it all at the same time and we had everyone working together. This was to create a whole new set of values. And because we’re a visual company, everyone made things that were already visual.

You can create really meaningful virtual experiences like this where the teams get to break away, work together, come back together, share ideas and thinking. It’s all done remotely across a number of different time zones. Which brings us to another point. Wherever possible, we’re trying to steer people to doing work that is asynchronous.

Now, traditionally speaking, asynchronous has meant you’re going to have to read long docs, right? But that’s changing a lot with tools like Loom. This is a tool that we use a lot in the office, by the way. You create a screen recording with your face and you talk through something, do a demo, explain something, give feedback and you just post that into a channel and people read it and pick it up as and when they want to. So, with voice notes, written docs and video docs, you’re able to do that asynchronously.

Obviously, the real thing that you want to get, the real value that you want to entrench with asynchronous work is this idea of learning how to write and make your ideas and your thinking timeless and accessible by anyone at any time. So this is something we’re moving towards and we’re starting to need it more now as the overlap between our time zones is getting to the state where we have maybe two or three hours between some of our employees.

Another important thing is switching from an office first culture, when you are constantly pulling information from people, to teaching our people to push context constantly. Honestly, if you are a remote worker, you should be constantly pushing what you’re doing, giving people access to your mind, not just to your output.

Another thing that we’re doing is dealing with the problem with deliverables. Being left alone to just get something done, especially when it’s a sizable piece of work, is high risk. It’s high risk for a business to just wait and see. One of the things we’re doing is really prioritizing this idea of emergent work from the earliest stages. This is pushing context. From the earliest stages, you are sharing your thinking around your work. So we have created tools that encourage people to share their understanding of the problem before they start to get into the solution space.

And just two examples of how we’re doing that at the moment.

On the left-hand side, you can see in Miro we all worked as a company on our 2020 OKRs and our Q1 OKRs. Everyone participated in a mixture of synchronously and asynchronously work, and Miro was literally our giant whiteboard with people pasting sticky notes as and when they had ideas and thoughts.

We encourage people to not just put finished work out in the open, but to put any work that they’re doing out in the open and to make this all accessible, not just to stakeholders, but to anyone who might be interested.

The big thing that we’ve had to learn as we’ve started prioritizing Remote-first is changing how we think about managing people and really looking for self-motivated people. This obviously has changed the way that we recruit people, but it’s also got a lot to do with the kinds of qualities that we look for in people who work.

I think it’s really important to note that remote working is definitely not for everyone. If you’re the kind of person that needs to have someone pushing you along to get to a deadline, at best you’re going to survive as a remote worker. You’re really going to struggle to grow. We really look for people who have an air of self-motivation and this has got nothing to do with seniority.

Office spaces and working in an office is a spontaneous environment, and when you move to a Remote-first culture, you have to be intentional about everything. And one of the things we’ve done is that, in order to make sure that everyone has the same experience, we’ve been very intentional about any perks that come by way of you being in the office. For instance, we’ve had physiotherapists as well as haircuts and grooming in the office. Any of those benefits we’ve made available to remote workers as well. And this is something important. You might not have a lot of benefits, but if you give some, make sure that is something that everyone gets to experience.

For those of us who are leaders, who are designing the environments in which our employees work, the task is to avoid this idea of remote people, remote being the perk, remote being the other way.

As long as you have an Office-first mentality and approach to work, you at best are going to have people who are just getting through the work and you’re going to struggle to nurture and develop people and retain people longer term or reasons beyond just creature comforts.

But if you become Remote-first, if you become explicit around defaulting towards remote, even in your office environments, what happens there is that you create a company that exists as a set of ideas, agreements, you have a shared experience that you’re able to export anywhere in the world. And that is a far more powerful and far more scalable way of working.

Remote-first Drake approves.

We can talk endlessly about remote work because we practice it ourselves and believe in it. But, the words of СEO’s and СТО’s of other startups with teams distributed around the world will sound much more convincing. Go ahead and check out the recording of Shawn’s “Remotish” presentation at our Remote-First Conference here.

And in the end, three steps not to postpone, but to act:
1. Create an account
2. Start trial
3. Hire remote with



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