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How to lead your remote sales team to success

Managing (and growing) a remote sales team can be an interesting challenge for sales managers. Learn about the best tools and strategies to propel your sales team’s success.

An illustration of a remote sales worker

Working remotely can be a double-edged sword, even under the best circumstances.

While many employees savour the opportunity to work remotely, it’s also a huge change that presents challenges your team may not have faced before. Throw in a global pandemic and a sudden shift to working from home full-time without a chance to prepare, and remote work can feel like more of a burden than a blessing.

As a sales manager, part of your job is to lead by example. Your team looks to you to provide direction, especially in periods of uncertainty and change. In order to smooth the transition to remote work (or to optimise the experience if your team has been working remotely for a while now), you need to understand the hurdles your team is facing so you can provide practical solutions to overcome each one.

In this article, we’ll help you identify the top challenges for remote teams along with tools and strategies you can use to propel your sales reps’ success. We’ll touch on practical considerations for how to best manage (and possibly even grow) a remote sales team as well as some of the psychological elements that impact remote salespeople.

The core challenges facing remote sales teams

Illustration of the 4 greatest challenges facing remote sales teams – communication, scheduling, performance evaluation and culture

Challenge 1: communication

Whether you’re in the office or in your living room, a breakdown in communication can hurt workplace productivity and morale.

In the context of remote work, it’s up to you as the sales manager to set the tone and ensure everyone has access to the tools they need to communicate effectively. That means helping everyone get set up, providing access to any necessary training and holding team members accountable for their participation in important conversations.

As a general rule, it’s better to over-communicate than under-communicate. Otherwise, employees might start to feel isolated from the team or disconnected from your company’s core values. Plus, without frequent and honest check-ins, you’ll struggle to know what’s going on with your salespeople – which makes it impossible to motivate, monitor and troubleshoot. Explore virtual team building exercises too to better engage your employees.

Challenge 2: scheduling

When all or most of your employees work from home, scheduling a team-wide meeting can be a nightmare. Since your sales reps can technically live and work from anywhere (as long as they have a good internet connection), you may have to account for different time zones on top of your team’s already busy schedules, sales calls and client meetings.

Sometimes, the best you can do is choose times that fall within the traditional ‘9 to 5’ for everyone. This sounds simple, but is often easier said than done. Rather than setting a weekly standing call, it might be necessary to rotate times to accommodate team members in different parts of the world. Or if that’s too inconvenient, you may need to consider splitting team-wide meetings into several calls instead.

Alternatively, use Dropbox Capture to record video messages and share narrated screen recordings. This allows teams to review in their own time, instead of trying to coordinate everyone’s calendars for a meeting.

Challenge 3: culture

How do you bond as a team when you can’t physically spend time together or chat at the water fountain? Team building is important in sales not only because it’s great for team morale, but also because a sense of camaraderie often sparks friendly competition that motivates individuals.

The lack of face time can lead to cultural degradation and feelings of isolation. In fact, about one in five remote employees experience isolation (19%) and struggle to unplug from work at the end of the day (22%).

How big is your remote sales team? If you’ve got four or more reps on your team, it’s likely that at least one of them is experiencing a negative mental impact from working from home. Building a positive, open remote work culture can help mitigate these feelings.

Challenge 4: performance evaluation

It’s a common misconception that remote workers aren’t as productive as those in the office. If this is something you’re concerned about, consider that 77% of remote workers say they are more productive working from home than they are in the office. For sales, in particular, it doesn’t really matter where you work from as long as you have access to the right tools, information and reliable internet connectivity.

That said, going remote presents real challenges for sales managers looking to monitor their team’s performance. Beyond measuring end results (i.e. total deals closed and money earned), there’s a lot going on behind the scenes that can be hard to keep tabs on when you’re managing a remote team.

How can you provide helpful, relevant feedback if you’re detached from the day-to-day activities of your sales reps? After all, sales involves much more than just selling. You need a way to track progress and ensure your reps are pulling their weight before it impacts results.

Strategies for effectively managing a remote sales team

As a sales team manager, you likely have a few (valid) concerns about the switch to remote work. While you want to create the best possible work environment, you also want to keep driving the best sales outcomes possible. Thankfully, the right mix of strategies can help you manage and inspire your remote sales team from anywhere.

Illustration of a puzzle with title The missing pieces: tips for better remote sales team management

Maintain open lines of communication

True communication is a two-way street. Whether some or all of your employees are remote, it’s crucial that every single person on your team knows exactly how to reach you with questions or concerns. Set a precedent by replying promptly (within reason) during your work hours, so sales reps know they can count on you for guidance.

Ideally, you should choose an instant messaging platform (like Slack or Google Chat) that allows communication to flow freely without the stuffiness, formality or lengthy threads that can come with email.

Open communication also requires collecting feedback on a regular basis. You can ask for input on specific issues via email or give employees the chance to reply anonymously with a survey tool like Typeform.

Make time for one-on-ones

There’s a time and place for team-wide calls, but the last thing you want to do is neglect your remote sales reps on an individual level. As a leader, your team looks to you for guidance, quotas and motivation.

Whether or not one-on-ones were part of your in-office culture, you can and should conduct them remotely via video or phone call. Not only do one-on-one meetings allow you to get to know your team members, but they also give employees an opening to ask questions, speak freely and receive performance feedback without worrying about who else is listening in on the call.

Set clear, measurable goals

When it comes to working remotely, one of the keys is to over-communicate. Don’t leave anything open to interpretation. That means setting specific, achievable goals attached to deadlines and clear expectations. Use challenging-yet-realistic quotas and actionable KPIs to motivate employees to hit their targets. It’s also important to create a well-defined job description, so each employee knows exactly what’s expected of them (especially as your team expands and sales roles evolve).

Recognise and celebrate wins

Everyone deserves recognition for a job well done – especially remote employees who might lack the day-to-day social feedback that promotes team bonding. On top of announcing each win on Slack (and maybe doling out a taco or two in appreciation), consider hosting virtual award nights to express gratitude for your team’s hard work.

Host virtual social events

Just because you can’t go out for end-of-week drinks doesn’t mean happy hour has to go out the window. Organised virtual happy hours, lunch chats or coffee hours give your team a chance to socialise, bond and share ideas.

When your team gets along, everyone benefits. Even a quick chat can serve as an important reminder that behind those screens and profile pictures, you’re all human. This creates a sense of belonging, increases loyalty and motivates employees to work together rather than against each other – which is also good for productivity and sales results.

Invest in shared tools

Empower your reps with access to the right tools and technology, like Dropbox for teams. Keep reading for our list of recommended tools for creating your very own remote sales tech stack.

The ideal tech stack for remote sales teams

Bundle the following tools and technologies to build a sales stack for successfully managing a remote sales team.

Illustration of the ideal remote sales technology stack

Cloud-based CRM

A CRM platform allows your team to track, analyse and share information about the sales pipeline — including prospects, forecasted revenue, deal progression and pipeline value.

Since a cloud CRM can be accessed from anywhere, you can monitor how each of your reps is performing (and how much potential value they’re bringing in) from the comfort of your home office. By tracking how quickly different team members move deals through the pipeline, you can improve forecasting and address bottlenecks.

Shared calendar and scheduling apps

Simple scheduling tools like Calendly and Doodle allow teams to find specific times that work best for one-on-ones and group calls.

Whether your team has a shared Google calendar or plans everything through a workflow management platform like Asana or, there is a huge range of technology built specifically to keep you and your remote sales reps on the same page.

Video messaging and recordings

If you have a major announcement that your whole team should hear even while they’re spread across different time zones, why not create an audio recording or Loom video that can be watched at each salesperson’s convenience? You can share hi-res or compressed audio and video files with Dropbox.

In fact, you might also consider recording important calls to ensure everyone has access to the same information (without requiring anyone to join a call in the middle of their night).

Communication platforms

We touched on the importance of over-communication above. With so many user-friendly chat and messaging tools available, there’s no reason for miscommunication over important items like sales quotas and job expectations. Plus, many modern communication platforms make it simple for teams to form and maintain social bonds at a distance. Whether you use Slack, Google Chat, Microsoft Teams or even Discord (or some combination of the many available platforms); remote teams rely on technology that makes it easy to stay in touch.

Secure eSignature technology

When you’re this close to signing a new client, nothing kills the vibe more than printing, signing and emailing a document multiple times for multiple stakeholders. And when your team is distributed, the process only gets more complicated.

The longer it takes to go back and forth with a customer to create an agreement and complete the paperwork, the less likely you are to close the deal. Fortunately, with the right technology, you can save time while still keeping close track of every deal, proposal and contract. In fact, sales teams that leverage eSignatures are able to close sales about 17% faster compared to the manual signature process.

Using an eSignature tool like Dropbox Sign lets you skip the paperwork altogether. The electronic signature platform empowers your sales team to create secure sales agreements with minimal back-and-forth.

With effective management, remote sales teams can thrive

If you’re finding it more difficult than expected to transition to a remote workplace, you’re not alone.

Whether your company is changing to remote work or has been forced to work from home due to circumstance, switching to remote work brings new obstacles and changes to the way your team communicates and sells.

With the right mindset and access to the best tools, you can empower your remote sales team to thrive. Who knows, maybe you’ll conquer the challenges of remote work and find that your team is more productive than they’ve ever been! If your employees and leadership prefer it as a long-term arrangement, you might never work from an office again.

Find out how eSignatures can help your sales team close the deal.

Learn more about Dropbox Sign