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Zack Onisko
CEO at Dribbble
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Remote Career Summit 2020
June 25, 2020, Online, USA
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How to Build Culture & Scale Remote Teams: Dribbble & Creative Market | Arc.dev Remote Career Summit
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About the talk

Zack Onisko (CEO of Dribbble) and Chris Winn (CEO of Creative Market) shared their experiences of managing and leading remote companies. They had a deep discussion about how to build remote-friendly cultures, and the changes they’ve made while the companies grew. They also highlighted the importance of empathy, and how to create a virtual workplace to enable people to build personal connections online.

[Resources]

📝 Notes from this talk: https://bit.ly/2E0CYXr

🌐 Remote Career Summit: https://bit.ly/RCS2020-event

[Learn More]

- Arc: https://m.arc.dev/yto

- Dribbble: https://dribbble.com/

- Creative Market: https://creativemarket.com/

Arc helps you effortlessly hire world-class remote engineers and teams. Trusted by fast-growing companies including Spotify, Hims, Fivestars, and more. Escape the local talent war with Arc.

About speakers

Zack Onisko
CEO at Dribbble
Chris Winn
Creative Market at Creative Market

Zack Onisko is CEO at Dribbble, the global community for designers and creative professionals to showcase, promote, discover, and explore design. Dribbble was founded in 2009 and has grown to become the designer community it is today for tens of millions of people around the world. Dribbble is on a mission to build the world’s best platform fordesigners to gain inspiration, feedback, education, community, and job opportunities. Before Dribbble, Zack began his career nearly 20 years ago as a web designer before shifting into business and executive roles at Autodesk, Creative Market, Hired.com, BranchOut, Monster.com, and Tickle.com. He is responsible for scaling multiple companies to successful exits over the past decade including the Creative Market acquisition by Autodesk in 2014. Zack is a startup investor and advisor working with Indicator Ventures, Dwell magazine, Reforge, and others.

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As CTO, Chris leads Creative Market's largest team, which includes product engineering, Web Ops, and Search & Discovery. Chris serves on Creative Market's board of directors and executive team, spends time mentoring and speaks about management, technology and growing companies.

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The very next talk, we have Chris win from creative market and Zack offered Ripple and they are going to be sure I have Health Management scaling and remote culture of Pastor Chris awesome. Thanks. Great to have everyone here sobczak and I we know each other and we both starve are CEOs of remote company so that it should be pretty straightforward, but we'll see how it goes. Why don't we start by? Give me the backstory on Tribble as a remote company. I'll do the same for Creative market after

an 11-year old company. At this stage, there was, it's always been a remote company from the beginning, I took over the company about four years ago, it was eight people with brown the company now, to from 5:30. And yeah, it's it was always, I think it's at one point we thought about setting up an office in Oakland, which is close to where I live, and I'm in finally just backed out of that plan to stay remote has been great. So you have to jump into Tamaki, we've got so much in common, but that's one of the unique things or different things about creative Market. Story is We were we are we are all

remote. Now we have been for a couple years but has a history of the company is really interesting because we were running, we were predominantly remote but for a while we had an office in San Francisco and couple years ago and we kind of decided to to pick a lane and so we've got experience both making remote work but we've also had that transition. To that. I think a lot of companies right now or going through hey we haven't been remote. Maybe we're trying to be how we go to that kind of middle.

I'm so it's super interesting. So does the kind of thing that that flipped the switch in the major decide when you really do this. And it was you know it wasn't only my call, we talked a lot about it. As a team for most of creative markets have been in Creative market for seven years. I'm like an old timer at the company but I was almost always remote. I was hired remote at work remotely for years. I also had a couple years in our San Francisco office, so I

knew what that experience was like. But, you know, this sack like some good, some bad like great to see everyone everyday, commute a little tough. Not great. Not so much fun. And one of the things that I observed was we were we are kind of building two cultures and I like we had the office culture and then we have the remote culture and I think we just really wanted to like pick a lane and be really great at one thing. And I'm preaching to the choir right now, but remotes just got so many advantages, if you can if you can do it right. You forgot

one thing I'm really interested in where remote companies were were like built for these times but like is it? Is it particularly challenging right now? With covid-19 briefing going on like you feel like dribble is sort of built-in wired for this moment or have there been kind of the unique challenges along the way even though, you know, if you guys are have been all remote. It's this constant evolving process, right? We don't have anything set in stone in the way that we were always learning and trying

to do better. But we were very mindful from, you know, when we were just eight people and then started to grow the team, it's really double down in the two key areas. One is just like over communication. So a tiebreak companies that sidewalk with Matt passed, the remote team, sometimes gets lost out there a lot of data, the decisions are being made in headquarters and so we will want to make sure that didn't happen. I wouldn't have anybody who is, you know, feeling isolated on a Lonely Island. So that's going to make them into the DNA as we do a lot of things like a

weekly. All Hands. We do you know every direct report has a weekly 1 1/3 manager. Who told you about yourself like that? The other thing that I wanted to be a really big into the culture and it's something that we, you know, we kind of a bit heavy-handed in it even though you probably shouldn't be but it's just having fun, right? And so trying to connect people as humans and the goal is like even though that we're remote team and we have no people scattered all around across North America, we still want to have this Vibe and this personal connection that you get with

somebody. You know, walking to lunch and you know if you work together in an office until we have a really great. head of operations, Chloe who, who does a lot of really cool things like virtual Coffee hours, we do happy hours, we do games and then book clubs movie clubs and things like that better not work and just allow people to connect as people in our slack is, like, I'm sure like yours is full of like, the dog channel in the movie channel and like all this different Realms provides, just the culture in the tone, for the

company and ends, we found that You don't with a sense of humor and then when people can have fun together it really like lowers. Do you know if any kind of borrow of or or a facade of you know working session with somebody need to really be your true authentic? Sell those two things, communication, and having fun and then have you all figured out how to be good at turning slack off. I mean, you know, the thing that is true about remote culture, I think for a lot of companies as it's it's

hard to end the day. You don't have to drive home to kind of like transition back to another mode, you know, how do you guys manage that? So I'm really bad. It bad but like in between there, I'm hopping back on my phone, on my device. When it's something, I'm I'm trying to actively break apart from its. It's a bit of a benediction. It's working, Workaholics ISM. I tried to ingrained in the culture and I think for the rest of the team, you know, we had this, you do 40 hour work week will reflect no more, no less,

you know, we do no meeting Thursdays and Fridays and you know who Tyler Bond child, like the inner office meetings. Monday, through Wednesday and Thursday, Friday for engineers and designers and, you know, functions, we need like that heads down time that gets them, some buffer tube, really like focus and do some deep work for rolls like mine for a host. A lot. I spend a lot of my outside calls in those meetings with people outside the team on those days. You know, it's not a hard and true with something that you said we were bald over. I would like to

be more rigorous about sticking to those but you know, we are start up and things come up and we are mindful of that stuff, you know, we are trying to Me. Look at the pros and cons, you know, you don't have that commute you, you're close to your family and to get more time to see my kids grow up, which is a bonus. But, you know, it that's really kind of the big Advantage. What a lot of people are drawn to working for a fully remote. Company is allowed people to build a perfect day, until we've been super casual and relaxed about

working hours. And as long as people get their work done, what kind of like, you know, we trust you to get the job done. And you honestly think a lot of entrepreneurs in a lot of managers or talk to you over the years. Trust is the big you know blocker. Right. They don't trust their own people to get their work done. So anyway, Even for myself, my personal style, like I'm very much alike, just ride the wave you're on. If you're in that mode of your just like in a phase of creativity or you're working really hard on something like

just work really hard. It's okay. I think I need you to go to be mindful that I love of, you know, the other way of that needs to come into of like, hey, you know what, like, this is a different day. I'm not feeling that same thing, I've got to restore, I've got to charge a little bit, but you know, it's hard when we were, you know, by following us around everywhere, but we do the same thing. We tell the team all the time, you know, we, we work pretty hard. But you got to be really thoughtful about, you know, having fun. And taking some time off. I was, we had an all-hands this morning

with the company and one of the things that we were saying it's like you don't forget like yeah, we've always done that. We've been a remote company these past couple years, we've got remote built into our DNA but I think the thing that a lot of people are missing out on right now. You don't have those, you know, like I haven't been to a grocery store since March. Like I don't have those drives and those like, you know, those those moments to just kind of context which away from work. And so we're trying to tell the team like look after yourself take time off, maybe you can't do that trip.

You want to do right now but it's okay to still take a day off and just going to do whatever, or even know I've been trying to do a one-on-one spyfone. Because other than that, I'm having a blast here at this conference, but I think everyone's getting a little burned out on video just like go for a walk and get some sun on your face, talk on the phone. You know. I know you're a runner, I'm not one of the things I've just become really can find an inferno, the gems were open. I would go to the gym but it wasn't doing a whole lot of cardio and got a bike last year and started Friday

morning. I just felt like, just the mental Clarity, and I'll come back and that was really cool. The one of the things we just did a couple weeks ago, if we had a remote 5K with the team, and we have encouraged everyone in the company. We've, honestly, I don't know if you guys use Virtual coins and you can cash them out as cash and PayPal, or Donate them to your favorite charity. Whatever it was super fun like this team. Kind of scattered all over and we always encourage each other to go out and exercising and not work

again, a recurring theme that has like a way you kind of Bond as a company's is not always around project. I think I like for me personally and obviously everyone's guide got a different thing but that I'm it's really important time to recharge and it's like the old saying, like, you get your best ideas like finish our on a walk. It's because you're, you are stepping away from that like hyperfest feedback loop of chatting with someone over text. There's something like great about that when that's the right tool. And there's also something like not so good about that.

And you've got a I don't know, I don't know who she have to over, think about it too much, but it's it's something to be aware of, for sure. Any ideas, I want to get some more of that, that's good. Good job. So yeah, I mean, one thing I'm interested in trouble to, you know, eight people now, not a people. So how is has scale worked as you've been kind of building this remote company like what? What's maybe most the same when you were when trouble is much smaller and what spread very different and you had to like ripping apart and going to

put it back together again, that we have a lot of our processes overtime but even when we were small, we try to instill a lot of best practices. So he knew kind of as we grew that we would. We need a really good strong Foundation to support an inbro, the team. Yes, we do, besides, like the weekly communication stop. Well, really, you know, rigorous onboarding where a new employee meet, you know, everybody on the team wanted one, they get an arm boarding buddy who

kind of shows them around. And you know, you have a clock. All of our like internal your Buzz words and and things could only mean something. If you worked here for a while, slack documentation, do we put together that that goes through, like how to, you know, set up all your your notification mutants and in setting your hours and, you know? So that's that's really important to get that set up that you aren't getting buzzed at 10 at night. If somebody in another time zone is just wanted to share something. 3, how many things that we we

took a pretty good approach knowing that we were going to grow. And so we we put a lot of foundational things in place and then you have every different stage in size of a company in like, just a moment in time. A company just needs more last week, I was going to come from the place of like we don't want too much process, but just like just enough to keep all the pieces together to make everything into a coherent. He made me think of was some, you know, we I mean, turtles. Team trips, creative

Market, just Team traps. And it's it's really interesting to I think when when we had people come on board at one of the thing that happens is, you know, each other on slack and and video, or whatever. But, you know, even as a remote company, those in person moments are really important. I always remember the story of we have someone who, who, who pays a lot of attention to some of our marketing channels. And she, she said that during one of the team's trip, she just happened to meet one of our infrastructure engineer's and the other, in the past when it normally

cost most of the time just in work every day on slack. But, you know, they had a Actual conversation and I were talking for a while and started to build their, their kind of their work relationship and it totally changed how they interacted on slack when they went back to their respective and on like that next project, she was like, oh, I could go talk to him. He would have a really interesting insight into how to implement this, this technical thing, and and those the sort of connections, they, you know, they get built overtime with some of them get built in person to even if your

remote company. Yeah, that the in-person time is, is supervised by, but we have to have a team trip planned in March. And course I was, that was terrible getting pushed to next march, but we have we, we, we tried to meet up twice a year the last few years and, you know, What do I create a market? I think that with a hybrid, like people come to the office and then it's kind of like work as usual for a few days and you're still at school today in the chairs with their laptops. With dremel, I was kind of wanted to put laptops

down and really just try to really focus on making those connections. As you noticed those serendipitous, you know, friendships that he probably won't make over a resume, giving your normal function we meet up casually have a traveling circus design conference that is in a different city every six months or so. And I actually finances the TV of slimes are there, no team out but if we do a conference for one day, only have the rest of the week to hang out. We go to museums with you. Do tours and, you know,

Restaurants eating and drinking having fun packs, throwing axe. Talk about culture a little bit. How do you sync a dribble side? The culture has changed over the years. I love you, kind of redirected, they reshape to yeah, but I think that So the big a pollution with dribble is it was really kind of a side project for Dan and Rich to the co-founders that really grew organically over the years and became this other thing, right? This this community kind of really grew and blossomed into this scale that I think they didn't ever imagined

it would do grow to. And so there really wasn't a game plan previously. And so when I joined the company as a CEO I know lay down a mission statement. Give give a Northstar for what I wanted it to go, is the company and who are serving our mission is to help designers become successful, and $6 in the company. And I think those values helps really Foundation as well as for, for the culture of of who we were in the Reasons why I would wake up every morning. Come to work and why we do we do, right? so I think culturally that was very instrumental and

then delivering those values. It started to evolve kind of who we were as a company in and how we acted higher than, you know, one thing, one of the big ones from our values is not being afraid to take until a few risks. And I think when you put your building when you're designing a community for designers, there's a lot of inherent fear of like judgment and critique and and in a community backlash. And that's where the thing. And he wanted to make sure that we as a, as a

company, we weren't afraid to evolve and grow and sell. I think that's one of the biggest changes in the culture of the years, is really shutting. Some of that inherent fear that we stock up over years and a Clear Vision for the future. It's by far one of my favorite topics. It's, it's so interesting because the you know, creative Market, we have a similar story in a different story and the unique thing or different thing is in a creative Market in a similarly like it just took off. So you know it was

is a really really successful from from the early days and that served this really well for years. I think the challenge with that though is its it's easy to become complacent and it's easy to think this is working innovation in innovation, in rattle, it too much. And I think one of the things that we kind of evolved over the last couple years is Similar to that core value but just don't don't be afraid to look at things differently and and a really to get the best out

of the team, you've got to encourage a lot of voices and a lot of really contrarian kind of use of things and, you know, kind of you knows they gain when people are as a gang and and that sort of thing. And I think I think that's not so much healthier over over the last couple years, but that's the thing. I didn't get any, you know, anyone at any company, you got to keep an eye on of some sort of, like, what got you there is not always was going to get you to the next up and it's enough. And I even think it's a remote

on a remote team, but there's also less, I think you've got to be really intentional about building space and time to just calmly, talk through. Messi creative discussions. And this is like very tactical but even being comfortable on video and resume of like I think silence is a super bad things or go for Steve it is like a scary thing and it's like two seconds to get comfortable with silence like think think internally. And then talk and have those kinds of really rich conversations that you could have. If you were if you were all sitting on a couch together in an office like

you would be comfortable with silence. And for some reason it breaks on video recorder or two ago or product team did like an 8 hour left and just would like, you know, put pencil and paper. Dang, but I wasn't on the call but I can get Fielding of that silence. I had an experiment one time that I don't know if I give myself a passing grade on it. But yeah, I had like 30 40 people on a zoom call. And I mean, there's something about the mute button to that is very, very bad that we have not solved this yet. But,

you know, when you're speaking there's all these wonderful little human nuances. You know, you kind of start a sentence. You're not interrupting someone but you're kind of starting a sentence as a signal to the other person. Like, I'm about to enter into this conversation, you need to let me speak in a sec and you don't have that on on Zoom, everyone's muted and and nowhere else in life. Do we have to make a conscious choice to like physically click something in order? Just speak and you know the experiment that we ran one time I said, like everyone like, turn off your

mute, my glasses, go for it. Let's make this meeting really messy. Of course, where it breaks down is like, you know, if I got a seven in a two-year-old and, you know, there's like crying and screaming and a dog barking, and everyone's got their own kind of like, life stuff going on. So it looks like quite. So it is an example of like, how subtle some of the challenges are. But if you're, if you're running a remote company, you're very tune to thinking about these things. I think that like that empathy component is really important for

leadership because you can, you can kind of spot it even if you haven't quite solved it yet, I tried to put you on the spot, but I have a couple times after people turn their video on, yes. But they've been in a group setting. Yeah, join in the conversation. I was just thinking about your question from earlier about, what kind of changing the culture. Another big thing that that came out of kind of studying those values and really studying at Northstar for the companies you know, for the first year or so.

I was the blocker for everything. Like everyone had to ask me permission to do things and so is like a weird like slowly had to give, you know, it's his delegation right in and then asking the people on my team to delegate to their teams like really trying to let go. I think, I think as a product person, you know, you're used to building with your hands and, you know, has as a leader, you looking to have to let that go and I think we've done a really good job of delegating and really, just giving people freedom to run and then figure stuff out on their own.

It's it's an operation will always have room for improvement. How have you two talked about hiring, you know hiring remotely easier harder. What does that look like for you all? So a lot of I made some mistakes and big mistakes and spend some mistakes over the years. What are hired some really big names from big companies and what is a leadership role and how to quickly rewind this decision. Cuz I learned that when you pull somebody from San Cisco and

there that used to play in Middle manager and a big office, it's really just a game of Delegation. So their whole job was delegation that they forgot how to work. So it being a remote team. It's very, it's clearly obvious when somebody's not pulling their weight. So that's that's the kind of one thing is, just making sure that we're hiring people who, who still have, you know, who is for sale, exercising, those those muscles and of their function. And it some level you graduate, here's the manager

and that's that's your function. But we got we got burned a couple times the other. I think you look out for his is there's people who are really there, like, 5 x, more efficient working from home. And then there's the people who are distracted by the sunshine and the TV is just not really built for them. Are they start to feel very lonely not being around people not having a social hour. So I think you are trying to read that out in the very early. Screening has helped you know find the right people for the team over the

years but you know the first year so we made some bad calls introvert thing and I'm like right down the middle but the kind of bias. Extrovert And we have someone, we leader at at our company and she is we are her first remote all remote company but she is very much someone that needs to see people everyday and connect with people and if she still needs that, you know, and so so I think one of the things that we think a lot about is like being real about what remote is and what it is in and and it's not that it's I don't know that it's, it's for people and it's not for some people. I

think it can be for everyone, but I think both sides have to try to negotiate and be real about what parts of it work super well and what going and how do you navigate that? And I think if you have those conversations up front, you can kind of you can. Part of it, you can get better results out of the hiring process than versus just kind of going in Eyes Wide Shut on some of those topics and not not just being open about it but we know we had similar challenges when we shut down our office. We said the people like, look, we're going to be different. We're not here to tell

you. It's going to be the same. It will be different and we hope for a lot of you. It's way better. And I think, for most people, it was way better. And I think, for some people, it was like, you know, I don't know about this. I'm not sure about this. And yeah, we were just our message was, let's just be open and talk about. It doesn't have to be a scary topic. So we do have people, who are we, do have a fair, even split of introvert, extrovert on our team and we do, you know, we have like a coffee fund with $50 at work baby

automatically. So that you're not just squatting at coffee shops, cuz people have to move. So sometimes just like being stuck at home is to isolating. So we have people who are just like, I want to miss copy shop, remove to the deli or you don't move back to the house to change out. The environment will have a couple people on the team who have, you know, co-working spaces in Rockford Meijer to be around more people working I'll grab a question really quickly from folks. We got a few minutes here, how? How rare is it that you

hire a developer without much experience into a senior developer position? So, at least a creative Market are our roles mean things. We, we care a lot about to the power defining levels and that's important for the company because we want to be thoughtful, and intentional about are hiring strategy, and ends up of what, what we're putting in place to support with the company's doing. But, but it's also about fairness to the Haitian. I'm coming in with individuals about about

career progression about development. And so that that's what of alignment is really important, you know? And I also think it comes down to That the size of the team because you also want to make sure that it is if the company is bringing me and really Junior talent that comes with all kinds of wonderful, great things. But it also means that the team around them, they've got to be able to support that person and help them grow. And it really it's, I mean, in the case of a developer, you think

technical skills first, but it's actually way more often times about communication skills, especially in a remote company. How good are you at over communicating? Zach was talking about earlier, setting expectations on Deadline, something like that. You really need kind of an orbit of of more senior talent to give that person kind of a fair shake and a shot at developing the right way. We think about that. A lot of you, I know gerbil does does too but the really good question. I thank you. Thank you so much.

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