Remote Sales Leadership: Thriving in A Virtual Sales Environment

Posted by Mark Ackers

The pandemic turned us all into remote workers overnight – and now the genie is out of the bottle. Recent data from HubSpot shows that salespeople are currently working:

  • 42% fully in-office
  • 33% fully remote
  • 26% hybrid

This presents a massive challenge for sales leaders who want to give their reps the flexibility they demand but still have targets to hit.

We sat down with MySalesCoach expert Aaron Margolis to discuss the challenges that heads of sales face when leading remote teams and how to overcome them. 

This article is part of our essential guide to Sales Team Leadership.


We'll Cover:


Navigating the Shift to Remote Sales Leadership

Transitioning to remote work presented considerable challenges to sales leaders and their teams. Everyone used to be together. But today, your team could be thousands of miles away. However, both sides have risen to meet these challenges, with coaching a significant factor.

‘Sales leaders have become better, and salespeople have become more comfortable with interacting remotely. A sales leader can watch Zoom recordings, be part of the conversation, or be a silent partner coaching on the spot or right after an interaction. Now, I think people are perfecting it.’ – Aaron Margolis


Effective Communication in a Virtual Setting


Choosing the Right Tools for Remote Communication

When you lead a remote team, you need to interact continually. While there are a myriad of shiny tech tools out there, you can get by with simple instant messaging and video conferencing if that’s all you want.

Really, it’s not about the tools you use; it’s how you communicate. You must communicate clearly to make your salespeople feel like part of the team, hold them accountable, and issue instructions.

’They may live in different countries, but you have to make it seem like they’re in the office next door.’ - Aaron Margolis


Sales Coaching Playbook

Building Trust and Rapport Online

Wherever your reps are in the world, you need to create that cohesion that makes a team. Here are some strategies to achieve this, even if you can only communicate online:

  • Make sure everyone plays a part in discussions
  • Acknowledge successes, however small
  • Provide constructive feedback
  • Work together to solve problems as they arise
  • Respect your reps’ time zones when scheduling meetings

If you're interested in finding more about inclusive leadership, we have an article on it here.

Getting the Most from Your Communication Tools

When it comes to tools like video conferencing, it’s essential that the sales leader and their team understand how the software works and the features included. Practise setting up breakout groups, whiteboards, instant chat, etc. All of this will make your meetings go much smoother and minimise delays.

Formulate best practices during meetings too. For example, how will you acknowledge someone who puts their hand up?


Personalising Remote Communication

‘One of the most important aspects of being a leader is understanding the pulse of your team.’ - Aaron Margolis

Talk regularly with everybody on your team so you always have a handle on what’s happening and can head off minor problems before they become significant.

Coaching is an excellent way to personalise these check-ins. It’s the most effective way to get to know people on your team on a deeper level than manager to salesperson. 

Build an understanding. Find out what makes them tick. It’s all invaluable to drive performance. 


Streamlining Communication Processes


In remote teams, it’s vital to keep information flowing between everybody. Here are some tips to help you:

  • Keep recordings and notes from all meetings
  • Use your CRM to keep a chronology of events as they take place
  • Ensure everyone updates their CRM regularly (even if they don’t want to)
  • Use project management software to keep tabs on ongoing work

As well as facilitating better communication in your teams, keeping detailed records helps your team if people leave, join or change roles.


Enhancing Clarity and Conciseness in Virtual Communication

Talking human-to-human is always the best way to communicate, as the sentiment in emails and text can get lost in translation.

‘The leader needs to tell the salespeople that we’re not going to solve problems by exchanging emails and texts. Instead, we solve problems by talking things through. If I need to provide constructive feedback, I’ll do it in a respectful manner. And I want to hear the issues you’re facing.’ - Aaron Margolis

But don’t waste people’s time. A good sales leader should always be clear and concise. 


Overcoming Remote Leadership Challenges


Managing Time Zone Differences

Time zones can be challenging when you have people in your team spread out across the globe.

Regarding meetings, work with your team to find the times that fit best for everyone. There may have to be some give and take. For example, if you schedule a weekly team meeting at a time in the morning where most of your salespeople live, the rep who lives on the other side of the world may only need to attend once a month. 

It’s essential that your reps in different time zones don’t feel isolated, or somehow lesser members of the group. Be creative as you find ways to work that help everyone. 


Handling Technology Challenges and Limitations

Unfortunately, technical hitches come with the territory in remote work, especially on video calls. Research by Dialpad found that audio issues (e.g. sound dropping out) are the biggest pain point. 

You can’t eliminate technical problems, but you can minimise them by ensuring everyone on your team can access a good internet connection and uses it for meetings (rather than unreliable mobile data). 


Cultivating Engagement and Motivation Remotely

’The way you motivate someone 20 feet away from you and the way you motivate someone 2000 miles away from you shouldn’t be that different, right?’ - Aaron Margolis

Set up regular check-ins and coaching calls to keep your team motivated. You should also make an effort to involve everyone in sales meetings, assigning extra responsibilities to top performers. Make them feel like they’re next door, not 2000 miles away.


Navigating Difficult Conversations Virtually

Difficult discussions are more complicated when they’re remote rather than face-to-face. But with a bit of thought, they shouldn’t be too different.

Take some time to consider the most respectful way you can set up the conversation. For example, consider the time zone of the person you’re speaking to. Tell them clearly what you want to talk about, so you don’t raise their anxiety.

Of course, coaching is the best way to address issues. Set an agenda, ask the right questions clearly and concisely, let them see your face and reactions. Break down those virtual barriers and make it as much like a face-to-face chat as possible.

if you're interested in finding more about managing underperformance in sales, we have an article on it here.

Developing Remote Sales Leadership Skills

‘Communication is the most important skill for remote sales leaders. You can have goals, ideas and targets. But if you don’t communicate with your team on a consistent basis, it’s going to break down.’ - Aaron Margolis

No matter how far away you are, make sure you’re still involved in your reps’ sales calls. Go out on ‘virtual calls’ together, then provide instant, constructive feedback. Don’t micromanage, but ensure you always know what’s going on.



Sales leadership is hard, full stop. However, remote sales leadership shouldn’t be any more of a challenge. The principles of leadership remain the same wherever you and your team members may be.

The trick is to break down those virtual barriers and make everyone feel like they’re in the office together, even if they’re on a different continent from you.

You can achieve this with excellent communication, technology (but don’t rely on it) and regular coaching. Follow our tips (adapting them to suit how you work) and see how remote sales leadership suddenly becomes more straightforward.


FAQs - Sales Leadership in a Remote Work Environment


What are the key challenges of leading a sales team remotely?

Communication is the number one challenge. You have to ensure you effectively and consistently communicate with all members of your team equally. Make them feel as much part of your team as they would if they were actually sitting next to you.

Holding your reps accountable is another common challenge. Even if you’re separated by distance, you still need to know what they’re doing. 

Finally, personalisation. You still need to get to know your people on a deeper level so you can manage them in a way that gets the best out of them.


What are some best practices for conducting remote sales meetings?

Interactivity is the key to great remote team meetings. There’s nothing worse for a salesperson than to hear their Head of Sales droning on and on - and you can see it in their faces that they’ve tuned out.

Act like a Master of Ceremonies as you lead the meeting. Start on a positive note by recognising and celebrating successes. Then, bring other people into the conversation. Let them lead different parts of the meeting to add some variety. 

Get feedback from your people on your meetings. Use it to identify ways to improve.


What strategies can I use to maintain team cohesion in a remote setting?

Team cohesion is essential to success. It’s something you absolutely have to foster in your remote sales team.

Technology is your friend. With your CRM, file-sharing tools, video messaging and more, there are many things you can do to create strong team bonds.

Create events when you and your team can work together, such as getting everybody on Zoom for an hour to do prospecting. Afterwards, get everyone to share their ‘war stories’. Things like this promote a ‘one for all and all for one’ mentality that transcends virtual barriers. 


Can remote sales teams be as effective as in-office teams?

Of course! In today’s environment, they have to be.

Today’s top salespeople don’t want to be tied to the office five days a week. They demand a remote or at least hybrid environment to work in. And if they can’t get it with you, they’ll move somewhere where they can. In reality, you have no choice but to make it work.

Organisations also see the benefits of remote work, finding that they don’t need to pay for massive offices. They also have access to a global talent pool.

So, look on the positive side. You get to work remotely too - and there’s no reason you can’t be successful just because your team is distributed across the world.


How can I promote work-life balance for my remote sales team?

One of the by-products of remote work is the feeling that you have to be ‘always at work’. Do not make your team members feel this way. 

Don’t contact your people after hours or at weekends, and discourage your team members from contacting each other out of hours too. Bear in mind time zone differences and ensure others do the same. When you check in with your team members, make sure they’re taking regular breaks. Look for signs of burnout.

Finally, lead by example. Encourage your team members to interact on a deeper level by sharing information about your personal interests. Walk the walk - and make sure work-life balance becomes an integral part of your team atmosphere.


Find out more from MySalesCoach

At MySalesCoach, we help busy sales managers and ambitious reps reach their potential with expert, consistent 1:1 coaching.

To find out more about MySalesCoach, book a call with us today.

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