Virtual leadership: Managing sales teams remotely

In many ways, the pandemic has forced sales teams to become more efficient. Many teams have switched to a digital-first approach, which allows for more interactions on a daily basis. It also means spending less time and money on commuting and traveling.

However, remote sales teams have a bigger hurdle when it comes to forging genuine human connections—and not just between sales representatives and customers, but also between one another.

For sales managers, the greatest challenge of virtual leadership is learning how to engage, help, and empower a team of reps you don’t share an office.

How to build a remote sales team

There are many budgetary and logistical questions to consider when building a virtual sales team. From a management perspective, the primary concern is establishing a human connection with sales reps you may never see face-to-face.

Hire a diverse sales team

In the past, sales managers have often tried to recruit employees who share a certain set of behaviors.

Don’t assume you need to assemble a mobile sales force of like-minded reps with identical skillsets. Instead, hire a range of personality types to create an agile team.

“I just want a group of people that have a baseline of wanting to work hard, wanting to constantly learn, and being open to receiving feedback so that learning can happen in real-time,” Tom McConnel, a Senior Sales Manager at Zendesk, says. “As for the rest of it, I want them to be as different as possible. Because then they’re all going to come with different ideas and approaches and angles, and that’s what truly builds a really dynamic and adaptable team.”

Get to know your team

Getting to know your sales team and help each rep grow can be challenging in a virtual environment.

It’s a problem that Monica Telles faced when she took a leadership role at Zendesk just two weeks before a Covid-imposed lockdown.

“Because I have a global team, I wonder when I’ll ever have the opportunity to meet some of them in person,” she says. “In the past, you would typically build relationships in the office, and that’s how a lot of mentorship and career progression would happen.”

Tom experienced the same difficulty when he had to bring on a new sales team remotely.

“I want to establish a personal foundation with everyone on the team, so that I can understand them beyond the scope of their work and they can understand me,” Tom says. “So when we brought in someone new, I’d get their number and introduce myself and say, ‘Hey, I don’t want to talk about anything related to work. I just want to get to know you. If you’re comfortable and close, let’s mask up and go get a coffee. If not, my calendar is yours and I’d love to just chat whenever possible.’”

Those sorts of casual interactions can form the basis of relationships that will lead to more professional development down the road.

“I try to set up mentorship meetings with other leaders within the organization,” Monica says. “And those meetings don’t need to be too agenda-specific, because then you miss out on building that natural relationship. But my biggest concern with the people I lead is making sure that they realize that there is a career path for them, and there are opportunities.”

Leadership tips for managing a virtual team

Leading a sales team will always involve trial and error, especially if you’re not used to doing it in the virtual realm. After having to adjust to the reality of managing sales teams remotely, both Tom and Monica say they’ve developed new priorities and best practices for guiding their reps.

Foster a sense of community that extends beyond your sales team

“When I managed a team in an office, the most important question I had for my reps was, how are you working cross-functionally and establishing relationships with people?” Tom says. “Of course, sales reps are going to talk to other reps and their BDRs and marketing partners. But what are you doing to talk to people that have nothing to do with your day-to-day?”

In an office environment, those kinds of cross-departmental connections will occur naturally as people meet and mingle. In a remote setting, it takes more effort to get your reps plugged into the larger company community.

“I think it’s even more important now that a sales rep talks to an engineer, or a person in IT, or someone in customer support and success,” Tom explains. “Someone you don’t share any accounts with, but you’re still establishing that human relationship and learning those tidbits of institutional knowledge.”

By now, most people are burnt out on virtual happy hours, so Tom tries to find other ways to “connect the dots” between employees. For example, when someone on his team relocated to Chicago, Tom facilitated an in-person meet-up with other Zendesk employees in the area.

“He doesn’t have any overlap with any of those folks in terms of accounts, but we just said, ‘hey, we’re going to have dinner, come meet some of our partners,’” Tom explains. “And I think that kind of community is so important now that we all feel so remote and we don’t have the same kind of communication that we used to have at the water cooler.”

Don’t let virtual meetings dominate your team’s schedule

Your remote sales force is already spending a ton of its time on customer-facing calls, and each internal meeting puts even more on their plate.

“We tried a lot of different things early on because there was that ‘Zoom fatigue’ and we didn’t want people to get burned out,” Monica says. “So, for example, we tried a ‘no meetings on Wednesdays’ policy to give everyone more breathing room. But then our reps said, ‘Okay, but now my calendars are stacked full every other day.’”

Monica says that none of those experimental rules really stuck. Instead, she found other ways to make meetings less frequent and more engaging.

It’s also helpful if your team meetings feel like actual meetings, rather than lectures.

“Make sure that the meetings are very collaborative, and that every person involved takes some sort of ownership” Monica recommends. “For example, make sure each person owns a slide, so it’s not just one person talking at you the entire time.”

Encourage your sales reps to set boundaries

Managing a remote sales team can be a tricky balancing act.

On one hand, you want to foster a strong sense of community and make yourself available to your sales reps so they always feel supported. On the other hand, you want your sales reps to know that they’re allowed to unplug and unwind when they’re in danger of becoming overwhelmed.

“There’s never a good time in sales to take PTO, but part of what I’m trying to do is really force my team to take time off,” Tom says. “I had a rep who took the day off and then I got a Slack message from him. And I said, ‘Okay, thank you, but you’re on PTO, so let’s take your PTO. This is why I’m here as a manager, this is why you have a team around you.’”

With a virtual sales team, it’s challenging not to take your work home with you. That’s why it’s important to encourage your team to set boundaries, like keeping regular hours and not responding to work messages when they’re off the clock.

“It sounds silly, but you really do have to establish those boundaries so that when you’re off, you’re actually off, and you recharge your battery,” Tom says.

Develop a team-first virtual leadership philosophy

“I am not a traditional top-down type of manager,” Tom says. “I see it as we’re all in this together, and we either win as a team or we lose as a team.”

As a remote sales manager, Tom has developed a virtual leadership philosophy that emphasizes accessibility, honesty, and a willingness to get his hands dirty.

“I’m never going to ask someone to do something that I wouldn’t do myself,” he says. “So if you can’t figure out a quote, it’s not beneath me to go in and say, ‘let me take a crack at it.’”

By taking an all-hands-on-deck approach, managers are able to maintain more constant communication with their reps and contribute to the team’s overall success.

“Obviously, there are times where I need to be a manager and times where I need to provide guidance,” Tom explains. “But I try as much as possible to be on my team’s level and let them know that we’re going to figure this out together. And we’re going to move everything in the right direction, and the rest will take care of itself as long as everyone is doing the right things and focusing on their own growth and success.”

Leading remote sales teams with the mobile sales app

Virtual sales teams rely on a lot of tools to work closely together while being physically apart. Conversations happen in Slack and on Zoom calls, informational resources are stored in shared Google Drive folders, and important details about your prospects, pipelines, and clients are all accessible in your CRM.

It’s critical that these tools can be accessed from anywhere in the world, whether a rep is working from home or on the road. This is why Zendesk developed their mobile sales app, which leverages sales AI and provides all the functionality of a full-fledged desktop CRM right on an iOS or Android phone.

As reps return to the field, they can use the app’s geolocation capabilities to map out all of their prospects and customers in the area. And after each sales meeting, they can use the app’s voice-to-text technology to quickly take notes in the CRM. That makes it easier for reps to be on the move, and easier for managers to let them do their own thing.

“As a manager, I worry about how much admin I’m asking for,” Tom says. “There is a baseline minimum. I need your forecast, I need your MEDDPIC, and I need your next steps. But anything beyond that is just busywork, and salespeople hate busywork, regardless of how much they love doing what they do.”

With the Zendesk mobile sales app, reps can share info through their phone while they’re on the go—whether it be visiting a client as we return to work or juggling work-life balance in this virtual setting. This allows them the flexibility to work on the go and ensures that all their notes and important details are saved directly in your CRM.

“The app helps prevent that tribal knowledge from just being stuck with someone who’s always out on the road, and then when they leave and you lose all that customer interaction,” Tom explains. “You can lose all of that unique, golden customer information if you don’t give your reps a tool that makes it easy to capture everything.”