Long Distance Leadership: Successfully Scaling a Remote Team to 50+ Employees

Nic Bryson is the Senior Director of Customer Support at Wrike. Since joining the company in 2009, he’s grown Customer Support from just one person to a remote team of 50+ members, spread across the globe.

In the past 10 years, remote work has grown by 103% in the US alone. Fueled by increased worker satisfaction, greater productivity, and an average cost savings of over $11,000 per worker each year, the growing trend of remote work shows no signs of slowing. The ability to effectively manage a remote team is now a must-have skill, especially for small business and startup teams who need to take advantage of the global talent pool and freelance workforce in order to find workers with the skills they need, on terms they can afford. 

While the benefits of remote teamwork are compelling, it’s not without challenges—particularly for managers and project leaders. Communication, tracking progress and priorities, and managing resources are all made more difficult by distance, in addition to logistics like time zones and language or culture barriers. Even with the right tools and processes in place to make day-to-day work easier with remote teams, a larger challenge presents itself: that of scaling your team alongside your growing business. How do you successfully train new team members and cultivate a thriving remote team culture? And how do you provide your team with professional development and growth opportunities, when you may only meet face-to-face a few times each year? 

Here at Wrike, we’ve faced these questions head on with our own Customer Support Team, led by Nic Bryson. Over the last 8 years, he's grown the team from just himself to a group of over 50 people, spread across North & South America and Europe. From onboarding new members to developing and promoting new Support Team leaders, Nic has experienced firsthand the growing pains of scaling a remote team, and shares some of the vital lessons he's learned along the way. 

Essential Tips for Hiring Remote Workers

Not everyone has a temperament that’s suited for remote work. Many telecommuters grapple with isolation, the pressure to be always on, and establishing a healthy work/life balance. That’s why it’s so important to go beyond technical skills and knowledge to consider whether a candidate’s personality is compatible with remote work. When you’re evaluating a potential new hire, what qualities should you look for? 

According to Nic Bryson, Senior Director of Customer Support here at Wrike, the key is to find someone who’s proactive: who will both seek out the answers to their technical questions, and put in the extra effort to connect with their teammates. 

In the support world, that means someone who isn’t just waiting for a new ticket to appear, but looking for ways to improve processes and projects. As a manager, this requires you to look deeper than the sheer number of tickets cleared or tasks completed, but the quality of work and willingness to go the extra mile. Who’s not only answering the customer’s question, but also providing them with related resources, or taking the time to follow up a few days later? Who’s considering how the work gets done, and looking for ways to make things more efficient or effective? 

The other important question to consider: is the candidate a people person? It may seem counter-intuitive that extroverts would pursue a remote position where they likely won’t interact with other people face-to-face, but Bryson says that drive to connect with others is essential. These are the kinds of people who will go out of their way to interact with their colleagues, whether via chat apps or video calls, and contribute to a successful remote team culture. 

Onboarding Strategies to Keep Remote Workers Engaged from the Start

Remote team members can’t simply stop by your office or lean over to a colleague in the next cubicle to ask a quick question, so opportunities to see how other people work and learn through observation are limited. Casual office chats or lunch conversations with colleagues from other departments don’t happen naturally like they can in an office environment, which can limit a new team member’s understanding of how the company functions as a whole. 

That’s why thorough training is a must when onboarding new team members. Remote managers must make the extra effort to be available to their teams, answering questions, offering ongoing support, and providing the training resources and context that enables cross-department collaboration. 

Bryson says, “It’s just as important for people to know what they don’t know—and also understand that they’re not expected to know everything. There are no bad questions, and people should always feel comfortable asking for help. They need to be able to self-serve, or know who the best person is to answer their question.” Make sure your remote team has access to ongoing training and is always encouraged to ask questions, regardless of how long they’ve been with your company.

"Servant Leadership" and Building a Strong Remote Team Culture

Establishing a vibrant company culture is difficult enough when your team shares an office. When you’re communicating via laptop, it’s that much more challenging to cultivate close working relationships and a collaborative atmosphere. And as your team grows, that challenge grows with it. 

When Wrike’s support team was only a handful of people, new members spent enough one-on-one time training with their colleagues that relationships formed naturally. As the team began to grow, however, Bryson says he made a point to establish a servant leadership mentality. People were promoted to management positions not only based on their job performance, but their willingness to support their teammates. Now, the leadership team consists of people who look for opportunities to help their direct reports and provide them with the resources and mentorship they need to excel in their roles and grow their careers. 

Tools like Slack allow the team to be in constant contact throughout the day, discussing everything from work-related issues to personal news and pop culture. People are encouraged to be open about any challenges they’re facing and to ask questions. Bryson says this openness helps them resolve process problems, which are more difficult to uncover and diagnose as a remote team where visibility is limited, and people can be more hesitant to admit that they’re struggling with an aspect of their work. 

The team also relies on Zoom for team meetings, which allows for up to 25 webcams. Bryson says having everyone turn their webcams on during meetings makes a big difference, letting the team get in as much face time as possible. “If someone doesn’t have their webcam on, their teammates will make a point to say ‘hey, we want to see you!’ It’s not just me talking to a black screen,” he says. 

It's important to remember that it's not just the frequency of communication, it's also the quality. When your team is reading your messages via email, chat, or the comments section of your work management software, important cues like tone of voice and physical expressions are lost. And when you add in language and cultural differences, those nuances are even more difficult to translate. 

Even common sayings that are second nature to you can be easily misunderstood by remote colleagues who aren’t viewing the message with the same cultural lens. Bryson recalls, “Early on there was a customer communication with a support team rep, where at one point the customer said, “You guys are killing it!” And the support person replied with something like, “Oh, I’m so sorry to hear that”—they thought they’d done a bad job—and it was just one of those instances where you realize how fast idioms and cultural context comes into play. And you have to make sure your team understands what’s meant by those slang phrases that they might not be familiar with.” 

As workspaces become more and more informal, the use of emojis and gifs can help make up for some of the context cues and make communicating with your remote team that much easier (and more fun!) 

Meeting the Challenge of Leadership & Career Development on a Remote Team 

While offering advice and guidance to your team is tricky when you don’t get a lot of face time, providing opportunities for career development is essential to keeping talented team members around for the long haul. If you want remote employees to grow with your company, supporting career development is a must. For Bryson, this is why weekly one-on-ones are so important. 

In a culture of constant communication, sometimes one-on-ones can seem redundant. Since Support Team managers are always available in Slack, questions get answered right away and conversations are ongoing. As Bryson explains, “Sometimes there’s this sense of, we’re already talking all the time, so what’s the point of having a separate one-on-one? It comes down to a distinction between training and development.”