Distant Collaboration: Finding Balance on a Fully Remote Team

Though remote work has grown in popularity in recent years, completely distributed companies with employees all over the globe and no head office are still rare. At SkyVerge, remote work has been part of our DNA since the start, and we now have over 30 people in more than half a dozen countries. 

SkyVerge is the largest developer of extensions for the WooCommerce platform and the creator of the eCommerce email marketing platform Jilt. We serve tens of thousands of customers with mission-critical software for their businesses, so as we grow, we’re continually iterating on the ways we work to keep our team feeling connected, fulfilled, happy, and able to meet the big work challenges we face. 

But what does it actually mean to work on a remote team like SkyVerge? How do we communicate and what does our day-to-day look like? I sat down with some of my colleagues to chat about the SkyVerge experience what it’s like to work remotely with a fully distributed team. 

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Catherine Scallen: Let’s start by going around the room and introducing ourselves. I'm Catherine, Head of People Ops for SkyVerge. I do a whole bunch of everything for the team, but mainly a lot of recruiting right now, a lot of interviewing, a lot of onboarding. I'm based out of Copenhagen currently and that's because my partner's studying abroad here. So, we're here through January, and then who knows where the wind blows us after that.

Jackie Casper: I'm Jackie. I’m a Rails engineer for Jilt and that means I add features, squash bugs—anything backend. So, stuff that has to do with the server. And I am currently living in Seattle. I just moved here from New York City and I moved here for the mountains and the nature and the greenery. But I also can see myself living a nomadic life sometime in the future, traveling around, seeing the world.

Jules Mittel: I'm Jules. I’m a Product Designer for SkyVerge, which means I'm kind of on the full design spectrum, especially for Jilt. Designing our products from the ground up, designing new features, user experience, user research. I'm based in Denver, because I love the mountains and could not imagine living anywhere else. I’ve also done the digital nomad lifestyle for a while and will probably be going back to that when our lease is up in June.

Tabitha Turton: And I'm Tabitha and I'm the Customer Success Lead at Jilt. Basically, that means I just work with our customers, focus on retention and loyalty, making sure that they achieve success, whatever that might be, with our app. Currently based in Montreal—I’ll probably return to nomadic life at some point, but for now, happy to be here.

Catherine: Okay, I’d like to start by asking if you had to give someone one pro tip about joining a remote team, especially if you haven't worked remotely before, what do you think they should know?

Tabitha: Self-discipline.

Jules: Yeah. Exactly.

Tabitha: You really need to maintain focus. You can't start letting yourself be distracted. When it's work time, it's work time, and you focus solely on that and get your stuff done.

Jules: Absolutely have a separate space to work. Don't work in your bedroom or from the couch  or… it's tempting, but I wouldn't recommend it. Have a space for work and then the rest of the house is for you. Once I'm out of this chair, I'm like, "Okay, work's done." I don't sit at this computer unless it's time for work. That and just time management, I think is the other big one.

It's extremely easy to get in the zone and just keep working. But you have to know your limits so that you don't burn out. It's really hard to sometimes manage that when you're just at home and you think, oh, I can sneak a few more minutes, which turn into hours before dinner.

Catherine: It adds up. You have to draw boundaries for yourself. And my favorite game to play—I just made this part of my job description, though no one asked me to—is the green dot game. So, if someone is supposed to be on PTO and I see them on Slack for longer than a short period of time, I'm like, "Hey, what are you doing? You’re on vacation. Why are you here?" Because it's so easy to be like, "Oh I'm just chilling, I'll just make sure I stay on top of it." But over the long-term that's how people burn out.

Jules: And it’s super nice that everybody at SkyVerge is very much like, it can wait. Whatever it is isn't so important that it's worth your mental time off.

Catherine: How have you found it, Jackie, as you're easing into it?

Jackie: This is my first remote job and it is very new. I think an important part to remember is to get out of your house. It's very easy just to live and work and stay inside all day and even order in food for dinner and continue to work. Something that SkyVerge does, which is great, is have a coffee shop budget. To be able to go out and get some coffee, just stretch your legs, go see other human beings… it's important.

Jules: For sure. And I didn't have that before, no coffee shop budget or anything. And I was always like, well, do I want to spend the money to go out? I mean, I want to get out of my house, but do I want to go spend five dollars on a coffee to go do that? Or do I want to spend money on a co-working space, but we also have a co-working allowance, which is fantastic! But just having the encouragement to leave helps a lot.

Catherine: I think one of my favorite parts about how we work is that we really have flexible hours and a flexible schedule. So, you can change where you work throughout the day. I have one place for calls and another for quiet work. You can switch up your environment based on the task at hand, which is really nice. 

Tabitha: Yeah. And I think that's really helpful for working remote, that you can break up your day like that. So you have that flexibility to manage your life outside of work. You're not stuck with that nine to five schedule.

Catherine: I was talking to a friend and she was like, "Oh no, I'm not going to be able to go on that trip—I have a lot of doctor's appointments coming up so I need my PTO." And I was genuinely like, "What?" It's what, an hour, hour and a half? So, instead we’re able to wake up early and do some work before going to the doctor or stay on later. 

Jules: And that's what working remotely should be. There are a lot of companies that work remotely, but still don't allow that flexibility. Even the few I interviewed with before SkyVerge—one said they’re a startup, so you could be working 60 hour weeks. If you're working 60 hours a week, then it's not true flexibility. You can't get out of the house, you can't… when are you supposed to go to a doctor's appointment or something? 

Catherine: That ties very nicely into my next question which is about inter-team communication. One of the things we try really hard to do is set-up the structure so that we can actually have that flexibility and we're not driving each other crazy or creating bottlenecks. Because even if you're in the same timezone as someone, there's no guarantee that anyone is going to be online at the same time as you. So, I'd love to hear about your individual and team approaches to how you work, what tools you use, and how you maintain flexibility.

Tabitha: We use a lot of tools, and I think that was part of the learning curve when onboarding with SkyVerge. But they're super crucial to our everyday work. Because a lot of our communication is asynchronous so we need to be able to leave thoughts or feedback somewhere. We rely on Slack, Basecamp, and Clubhouse to log all that information. 

Jules: Documentation is huge. When I started, that was a thing we were lacking, especially in the product area. We really needed to have our user research and user feedback and documentation from all of us about decisions, that were maybe made in Slack, which makes them hard to find. So, Clubhouse and Basecamp have been awesome. We try to keep all documentation in those tools and avoid individual Slack chats whenever possible. 

Tabitha: Everyone on the team also posts weekly updates to Basecamp. We all post either on Fridays or Mondays about what we worked on through the week, and that can be really helpful because we mention things that might have blocked us through the week and you never know who might have a solution. It could be from someone on a totally different team that happened to see.

Jackie: On the engineering team, Slack is definitely a place where a lot of communication happens and Clubhouse is also huge. We have our project stories there and can just tag anyone and ask them a question. And Intercom, when I'm working a support rotation, is also one of the tools that we use to communicate between teams.

Catherine: Can you talk a little bit about the support rotation? Because that’s one way you’ve gotten to know both the team and the product, right?

Jackie: It’s basically every three weeks or so we get a week [on engineering] where support is our main focus. We work on our other projects on the side, other stories, but the main focus is to look through those issues that come up on Intercom and to help out in any way that you can. And I think it's actually really valuable for the engineers because it has introduced me to such a wide variety of the code base that I normally would not have been interacting with. I remember, I think it was my second week, I was just automatically on support rotation. It was almost a trial by fire. I learned a lot about how things work, and where there were some issues, and what needed to be improved upon. And of course I had my team to go to if I had questions or could put something in the Jilt support Slack channel.

Tabitha: It's always really helpful when we get fresh eyes too. Because we get kind of used to things. You get complacent, and so it's always really helpful when someone new joins and it's like, "Wait a second… should we be doing it this way?" 

Catherine: And then that bubbles up into the product, right?

Jules: Yes. Definitely. I really love our support Slack channels. I can just kind of lurk in there and see what you guys are talking about, and it's really helpful for me. Because I'm like, okay, our users are struggling with this, where can I incorporate that into some of the feedback we're already looking at or the live testing we're doing?

Catherine: Okay, so, I would love to hear from all of you about conflict or disagreement. We talk about how we're iterating on things all the time—how do we reach those decisions? How do we solve disagreements?

Tabitha: What I like is that even when we're all in agreement, we look for the argument against what we're agreeing to. We seek it out, we want to argue, we want to debate, because we want to make sure that we're moving in the right direction. So, have we missed anything? We challenge ourselves to make sure that we're going in the right direction and we're open to making changes when we need to.

Jules: I think there's a balance, too, between knowing when to decide stuff yourself and when to kind of put it up to the team for debate. Because if everything is going up for debate all the time then nothing is ever getting done. 

If I have a solid argument and I put it out there and there's an argument that just keeps going, if nobody can decide on anything, you kind of need to know when to put your foot down and be like, okay I’m the product designer so this is my turf, it's going to be my decision, so this is what we're going to do and if it doesn't work, then we can iterate on it later. We'll test it with our users and see how it works.

Jackie: I don't feel like I've ever been in a position at SkyVerge yet where I feel like there's an argument per se. It's like-

Catherine: More a discussion.

Jackie: Exactly, it's a discussion and everyone has an opinion. This is the strong opinions, weakly held thing where everyone voices their opinion and then with that information we come to some sort of conclusion. And it's not disagreements. Everyone is kind of accepting of other people's ideas and wants to bring that in to get to the best result. And that's something I really appreciate about SkyVerge and our team.

Jules: My favorite part is that nobody's ever made me feel dumb or my opinion was too much or anything. Nobody's ever like, "Oh that's really stupid." Everybody takes everybody else's opinions very seriously and analyzes them and is like, Okay this is either really good or maybe this won't work because… but it's never been a negative experience, I don't think, ever.

Tabitha: Because it is a really supportive team. We're all working towards success, we're all driven to make this company better and I haven't experienced that before. Especially as a woman in the tech industry, that's not a typical experience, unfortunately. 

Jules: Totally agree.

Catherine: I want to shift a bit to talking about what the recruitment process was like for you when you joined. What attracted you to SkyVerge and why did you choose to accept our offer? 

Jules: I had been working remotely for four years prior, but it wasn't a fully remote team. So, 90 percent of that company was based halfway around the world, which left me and my remote co-workers feeling kind of forgotten. They just didn't have the right communication and stuff in place to make that work. So, what I was really attracted to was that SkyVerge was a fully remote company. And before applying, I looked at the public wiki, and the blog posts and tried to get a feel for if you guys were on top of communication with each other. Did you have the whole fully-remote thing down with everybody being located all around the world? Was everybody going to feel included? That was my biggest draw.

Jackie: I went through the hiring process pretty recently and to start it was just kind of an application into the wind. I was thinking about doing remote work, you had the right tech, and it seemed like a good place to apply. But as I started talking to people and as I started doing interviews, everyone I talked to was great. And I felt really comfortable with it. So, that was a major factor for me. It seems like SkyVerge has this way of doing things that was so well laid out. And even when we were discussing salary there was this whole document of where that comes from and the research that's gone into it. So, it just feels like a company that has these great, strong opinions on things, which I like as well.

Tabitha: It's really cool to hear your experiences, because I've been with SkyVerge and Jilt for about two years now, and my hiring process was a little bit different. But what really attracted me to working with the team was the culture itself. The personality that came through in the job posting was something where I was like, "Okay, I'm excited. I'd be stoked to work with this team." And then, like you mentioned Jackie, once you started speaking to people, I thought, "Yeah, I really like this person I want to talk to them more." And then, the next call happened and it's like, "Oh my gosh, this is awesome, I really hope it all comes together." And just having the opportunity to work with a growing company, because it means that you can try on different hats and explore and innovate.

Jules: For me, too, the general work that I saw I would be doing was a bit of an attraction. I hadn't had the chance to build a design system from the ground up, and had not used Figma. There were so many new things in the listing that I really, really wanted to learn and try. And you guys obviously had confidence in me to be able to learn those things, so that was good.

Tabitha: Yeah, and there's a work-life balance. That really stood out, because a lot of other remote companies I was looking at, they either made it seem like you were going to be at a yoga retreat on a beach somewhere, which didn't appeal to me, or that you were going to be putting in 80 hours a week. And that everything had to be perfect. So, it just seemed like a really good fit with this team. And it's paid off. I have the chance to work with incredibly intelligent and funny and driven people every day.

Catherine: One piece of feedback we get from candidates is, "This [hiring process] seems like a lot." And it is a lot, because we take it really seriously! We don't have a churn and burn philosophy; we want people with us for the long term. And a big piece of that is us feeling good about each other, right, and not like, "Oh, you can come in and do this job and then we don't really care how you feel here, because we assume you'll quit."

Catherine: How about when you joined? A question we get a lot is, "How do you get to know each other as a remote team?" So, I'm curious what was it like when you started? How did you get to know your team and learn about your work?

Jackie: I joined more recently, so I still don't know the entire SkyVerge team. But I got to know my direct team by needing to figure things out in my work, and I’d just reach out to people directly and ask them questions. I also have one-on-one meetings with Justin, my supervisor, and more recently I started doing donut chats, which are every three weeks where we’re paired up randomly with two other people to just talk, get to know each other, and introduce ourselves. And it's been really helpful to kind of get to know different people on the team and people that I normally wouldn't have interactions with. 

Jules: I don't know if this was the same for you, Jackie, but what I really appreciated was that everybody was kind of light on the communication my first week here. Everybody was very much like, "Okay, it's your first week we're not going to totally overwhelm you with stuff to do." And that's how I've tried to be with all of the new people too. I'll usually say, "Hey, I'm Jules" and introduce myself, but then check in a few weeks later and be like, "Yeah, how's it going?" Because yeah, that first week was like super-duper overwhelming for me. 

But the one-on-ones are especially helpful for me just to get with Beka, my supervisor, every week and work out our priorities and have a nice chat. It's never only about work, it's more like, "How are things going in your life?", "What are you doing this weekend?" It’s about how are you doing as opposed to how are you doing your work, which I find really nice.

Jackie: The [full team] weekly hellos, too.

Jules: Yeah, yes the weekly hellos. And again, it's not about work, it's just about getting to know everybody on the team, which I love, a lot.

Tabitha: When I came on we didn't do one-on-ones between team members. We just had all of our general team meetings and weekly hello. So, it was really the crucial bit that I found for getting to know everyone. Outside of having the opportunity to go and meet face-to-face I found those calls really helpful. But I’m really excited about our upcoming [team retreat] SkyTrip and to meet both of you in real life.

Because you can kind of cram in this bonding that would typically take place at the water cooler, whatever, in an office. We just kind of maximize it for that week. It's really intense. Lot of late nights with Scotch if you're interested!

Catherine: So that brings us to my last question, if you could tell someone one thing about what it's like to work here what would that be?

Jackie: I would focus on the people. I mean I like the product, I like the tech. I like all the things I work on, but the people are what really makes SkyVerge, SkyVerge. Smart, capable, nice, caring people that are also funny.

Jules: Yeah. Also that everybody is super encouraging. Not just supportive, but really, really encouraging. People give props and if you do something and you post it, they'll say, wow that's amazing. Even when I started, I thought I was going to be a lot more intimidated than I actually was because everybody was just so nice. Your first weekly hello is a little intimidating because you're like, oh my god there's 30 people here. But then you listen to them all talk and you're like, everybody's so nice and funny, and I have no reason to be scared.

Tabitha: Yup, and I think we kick it off really nicely with the gif party that we hold whenever someone joins the team. That was kind of just this organic thing, it just happened.

Catherine: Someone started it at some point, and people have really upped their games. They do themed ones, especially when another person from Canada joins. There's a lot of Canada gifs that get passed around. And then Artan's jokes!

Tabitha: Yeah, it's incredible. It's his own spin and we get these dad jokes. So, I wonder how it's going to morph over time. But I think that ties into, Jackie and Jules what you've said, it is all about the people. And from the moment you join and then while you're on the team meet-ups, it's just a really cool community.

Jules: Yeah, like earlier what Jackie was saying, when she was interviewing and talking to people and you were like, "Wow, these seem like people I really, really want to work with." That was definitely me. I mean I had other interviews going on and I basically canned them all. I was like, I want this job, I want to work with these people. And I was telling everybody, please pray that I get this job. And it all worked out.

Catherine: And here we all are!