Growing up remote: lessons learned from scaling a fully distributed team

Chloe Oddleifson
Dribbble
Published in
6 min readMay 1, 2018

Our team size has quadrupled, in just over a year. Like any distributed organization that’s seen rapid team expansion, naturally, we’ve experienced some growing pains. As Head of People Operations here at Dribbble, I want to share some advice and best-practices from lessons we’ve learned while facing some of the challenges that come with scaling a distributed team alongside a business.

Clarify your core values

As we began to grow in early 2017, we quickly realized the importance and necessity of nailing down our team’s core values as a team and company. Documenting what is most important to us, to share with the community and our new hires, was an extremely helpful exercise that continues to pay off today; our core values serve as a foundation for our organizational culture and have nurtured the sense of community we have among our team. They unite us. They are at the centre of everything we do here, and as we’ve grown, have served as a compass for us. We check all our decisions, whether they are related to hiring, product, or process, against them to make sure we’re staying true to our fundamental standards as we evolve.

Invest in team building

As a remote team, we found that as we grew, the organic opportunities for socializing together grew fewer and far between, and we missed that! Team building and spending time with your colleagues, whether virtually or in person, is a worthwhile investment in employee productivity, retention, and engagement. Don’t underestimate the cultural benefits to spending time with your team mates! We have weekly all-hands video calls with the whole company, where people can share what they’re working on, ask questions and give feedback on projects others are working on. We reserve time at the end of this call for free conversation and for sharing personal stories, so we can hear what’s new from everyone’s different neck of the woods! Plus, we get our team together in real life twice a year at Hang Time, run a monthly book club, and hold regular virtual happy hours where we get together to chat, catch up, and play games together.

Foster a culture of feedback

The doors to our People Ops and Leadership team are always open to hearing feedback, concerns, questions, or requests for feedback. Having said that, we didn’t just want our doors to be open — we wanted to actively be opening the door; taking a proactive approach on checking in with the team to make sure our people have goals to work on, are getting the feedback they need to do their jobs well, and most importantly, are happy coming to work every day. We have everyone on our team hold regular one-on-one’s with their manager. These are key to maintaining regular support and keeping lines of communication open. They also provide an opportunity for our team to get timely feedback on pressing issues, and a chance to set goals and celebrate recent accomplishments.

In addition to regular one-on-one’s, we have formal performance review periods company-wide, twice a year, in March and September. We’ve found that setting aside 2 weeks out of the year for reviews is a successful formula, rather than having everyone on a different review schedule.

The intention of these performance reviews is to review major accomplishments, highlight successes, set long term goals, and discuss career development. We’ve found that it’s valuable for our managers to have these conversations with their team on a semi-annual basis (at the minimum) to make sure that everyone is on the right career path for them, and making headway towards long term goals!

Be committed to improvement

Coming back to our core values, we’re firm believers that we should be constantly learning, teaching, and growing individually, as a company and as a community. We give everyone on our team $1000/year to facilitate continued education opportunities like online classes, attending conferences and reading books. Commit to prioritizing career development for your team — it’s an excellent way to boost engagement and employee retention!

Hire the right people, the right way

People are our biggest asset, and we have a very thorough hiring process at Dribbble to ensure that we’re bringing the best of the best on to our team. We have our candidates move through 3 rounds of interviews which include a phone screen, a team interview, and a hiring manager interview. Our interview process ends with a call with Zack, our CEO, who spends 30 minutes with every candidate talking to them about our roadmap, and the future of Dribbble. It’s imperative that our candidates understand our short and long-term goals as a company, and understand the role that we want them to play in getting us there!

Ultimately, the goal of our interview process is to give candidates an opportunity to see whether Dribbble is a company they could see themselves thriving at. For us, this means that they are 1) comfortable working remotely, and 2) passionate about the Dribbble platform and community, 3) they will raise the bar for our team and 4) they share our core values, which are fundamental to the way we work, the work that we do, and who we are as a team and as individuals.

We’ve learned that having our candidates speak with multiple people on our team gives them a real chance to get to know us, as a team and as a company. I’ve always said that on-boarding starts with the first interview! Not only does a thorough interview process help make on-boarding smoother, but it also helps us avoid hiring the wrong person, which can be a costly mistake. Our hiring process also gives our team a chance to have buy-in on a hire, and get to know their prospective team mate! Since we implemented our hiring process a year ago, we’ve had a zero percent attrition rate 💪

Go meeting free

More people means more meetings — or does it? We found that as we added folks to our team, we were getting sucked into more and more meetings; so much so that we barely had any time left to actually do the work we were spending so much time talking about in our meetings! So we now enforce company-wide meeting free Mondays and Fridays— and it’s been the best decision ever. The meetings that we do have we keep to 30 minutes, and if there’s no agenda prepped, we skip the meeting. By creating some guidelines and consolidating all our meetings into the other days of the week, we have more uninterrupted time to focus on the work we love.

Treat your team like family

I’ve always said that working on the Dribbble team feels like being a part of a family: our slack channels are full of dad-jokes, puns, and photos of people’s kids. We pride ourselves on doing right by our team by offering a perks package that we feel makes working at Dribbble a dream job, and something to be truly proud of. We are a family friendly company: we offer 3 months fully paid parental leave to both moms and dads in the US, and offer parental leave payment top-ups to Canadians. Offering a stellar benefits package is a key part of attracting top talent — and, speaking of our zero percent attrition rate — retaining them.

Ultimately, adding people, tools, and new processes is a key part in scaling a business, but like any kind of change, requires some adjustments and re-clarifying of priorities.The biggest lesson I’ve learned working for a company undergoing rapid growth is that growing pains are natural. Not only that, but they are an opportunity to improve: as a team and as a company. If you’re struggling with hiring or retaining employees, getting stuck in endless meetings, haven’t formalized your company values, or find yourself missing spending time with your team, embrace these as chances to re-think the way you do things to improve the lives of those on your team!

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