Managing a sales team can be tough, and when your team is remote it can be even tougher.
Without the ability to see and hear everyone in the same room, challenges arise in keeping track of what each individual is doing, and ensuring that everyone is engaged can be a daunting task.
Replicating the energy, osmosis, and momentum that comes with a team being in one place together is a major obstacle, but with the right tools and strategies in place, it is more than possible.
Incidentally, if done correctly, a remote team can very well be even more effective than an in-office one.
And if you want to be a cutting-edge leader in today’s competitive landscape, you better be able to get it done remotely – because one thing is for certain: remote work is here to stay.
So let’s dive in and cover all that you need to crush it as a leader in a remote environment!
In this article I’ll be covering:
1. What a remote sales team is and why would you need one
2. The benefits of having a remote sales team
3. How to manage a remote sales team effectively: 13 core principles to master
4. Bonus: Tips for staying connected with your remote sales team
5. The future of remote sales teams
What is a remote sales team and why would you need one
A remote sales team is a group of salespeople who are not located in the same physical space – pretty simple, right?
They may be in different offices, cities, or even countries.
These days the term most often refers to sales teams that work from home, although that isn’t necessarily always the case.
There are many reasons why you might need a remote sales team. For example, you might have a product that sells better in certain geographic areas, or you might be trying to reach a new market.
Or there might be a worldwide pandemic that suddenly forces everyone out of the office 
.
Whatever the reason, if you want to build a successful remote sales team, there are some things you need to keep in mind.
The benefits of having a remote sales team
The benefits of having a remote sales team are massive.
For one, it allows you to tap into a larger pool of talent. You’re not limited to hiring people who live near your office, which means you can find the best possible candidates for the job, no matter where they are.
Irrespective, what this really means is that you are able to hire the best talent – ‘A’ players in large part prefer the option to work remotely. Providing this option makes you significantly more competitive in the hiring market.
Additionally, remote teams are often more productive and efficient than in-office teams. This is because they eliminate distractions and allow people to work in the environment that suits them best, while also empowering them to have full ownership and increased autonomy over their work.
Finally, remote teams can be more cost-effective than traditional teams, since you don’t have to worry about overhead like office space and equipment. It is increasingly expensive to run and maintain an office, so cutting this out altogether can be a major boost for a business.
How to manage a remote sales team effectively
Now that we’ve gone over the benefits of having a remote sales team, let’s talk about the reason you’re here: how you can manage one effectively.
There are 13 core principles that, from my experience, you must master and execute to run a championship-level team remotely.
They are the following:
- Know what you’re up against ahead of time
- Communication clearly and often
- Hire the right people for a remote environment
- Nail your onboarding process
- Make your sales process airtight and repeatable
- Get in the trenches with your people
- Check-in One on One often
- Meet as a team regularly
- Eliminate nonessential operating mechanisms
- Get your KPIs and Metrics locked in
- Get the right tools and use them correctly
- Go the extra mile and put together team events
- Feedback makes the world go round
Let’s break down each one:
1.) Know what you’re up against ahead of time
For as great as it is, remote work is going to present you with some challenges – some of them obvious, some not so much.
It’s on you as a leader to know what they are ahead of time and get in front of them full force so that your team can focus on crushing targets instead of playing catchup.
The great news is, you don’t need to go through these challenges yourself to learn them- plenty of people (like yours truly) already have!
Pro tip: If you want to accelerate your growth in any area, learn from the wisdom of others that have already been there so that you don’t have to make the same mistakes they did.
You’re going to have people lose focus at times. You’re going to have people feel isolated. People are going to need more support than they let on. Things are going to fall through the cracks. Communication is going to break down. The team will be (literally and figuratively) distant from one another. You won’t have eyes and ears on the pulse of the team like you would in an office. You won’t get answers to your questions as quickly. You won’t get the same organic camaraderie with each other as you would in the office. The team won’t learn from each other as naturally or seamlessly. People will get loose on engagement. People will lose the distinction between work and home, and end up forgetting to unplug, leading to burnout. (Btw, all of these apply to you as well!).
You MUST fight these diligently, and consciously approach each from a strategic mindset, EVEN IF THEY ARE NOT CURRENTLY A PROBLEM – just because something isn’t a problem now doesn’t mean it can’t become one quickly. And believe me, if you’re not ahead of these they will become issues in no time.
Which is why you must…
2.) Communication clearly and often
A big area of growth for me personally in my career was around effective communication. I had a bad habit of assuming people: knew what to do when they didn’t, knew what I was thinking when they had no clue, and knew what to do when things were unclear – when in reality they would often just do nothing and/or wing it. To make matters worse, I would automatically assume it was their fault when issues arose instead of taking responsibility, because in my mind I had communicated clearly – so the fault couldn’t possibly lay with me, right?
Sound familiar? I know no one reading this has ever been guilty of the same thing, but maybe you know someone who has 
.
Needless to say, this isn’t going to cut it if your goal is to be an effective leader of a successful team.
Communication is the cornerstone of any healthy relationship, personal or professional.
And in a remote environment, communication that used to happen casually or without effort just doesn’t happen anymore.
The onus of ensuring that your team is informed, clearly understands what they need to understand, knows what to do if they don’t understand, and has the resources and environment to speak up if they need to, is on you.
In any communication, if the person being communicated to doesn’t receive the message correctly, then the communicator, by definition, did not communicate effectively.
Read that last one again ^.
When you’re remote the best strategy is to overcommunicate, overcommunicate again, and then overcommunicate some more.
While I was leading remote teams, when I had to convey an important message to an individual or the team, whenever possible I would use multiple channels.
For example, we would hop on a video call to discuss, and after I would send both a Slack and an email recapping (although it is not always appropriate to do both for recapping, use your judgment).
As an additional measure, I would have each person respond to the email confirming they read and understood what was being communicated, and to reply to me directly if they didn’t. This gave people clear direction on what to do, and the ability to ask questions they may have otherwise been hesitant to bring up in front of their teammates.
Pro tip: Apply this rule to slack (or equivalent messaging tool) as well and build it into the fabric of how everyone communicates with each other – when something is conveyed via message, it must be confirmed that it is received and understood.
It may seem silly, and at times it will feel like overkill, but building this habit and executing consistently on clear communication will keep a ton of major issues at bay.
3.) Hire the right people for a remote environment
One of the best ways to ensure your team thrives working remotely? – Hire people that thrive working remotely.
Easier said than done, but if done correctly it will make everything else that much easier.
Build into your hiring process attention and focus around how a candidate approaches their work remotely, their experience working remotely, their ability to work autonomously, and double down on landing candidates with demonstrable exemplary discipline and strong motivation.
Pro tip: Use interview questions that have the candidate take you through actual real-life experiences they have had, so that you can avoid getting generic answers that lack substance. I personally use the STAR method.
If someone doesn’t have experience working remotely it isn’t necessarily an indicator that they won’t be able to be successful, btw.
What you want to look for is whether someone can demonstrate that they can stay focused, on task, and productive even when no one is in the room with them watching.
If they can show these traits, along with the other traits you are looking for in your candidate profile, secure them with a great offer quick – chances are you’ve got a winner.
4.) Nail your onboarding process
Once you’ve got the right people in place you’ve got to get them up and running as smoothly and efficiently as possible.
Being in an office grants you a good amount of room for error when it comes to onboarding. There’s generally always something you can have a new hire do to occupy downtime – chat with their new coworkers, sit next to someone and shadow, etc. If you missed anything in your onboarding process they can easily ask anyone around them for the information.
When you are remote, however, you are not afforded those luxuries. Ensuring the top talent you just secured has a world-class onboarding experience is a top priority in any scenario, and it starts from the day of hire.
Maintaining this standard in a remote environment means everything must be mapped out to a tee, even what the person should be doing during downtime (there should and will be downtime) while they are getting onboarded.
The informal interactions that would otherwise occur in an office must be replicated via scheduled web interactions between the new hire and their coworkers – for both peers and leaders in the company. This is something that everyone must be on board with (see what I did there ) and committed to dedicating time and energy to.
This is also, like so many other areas, where feedback plays a critical role. You’ve got to check in regularly with new hires and quickly establish trust and rapport so they can give you the necessary feedback you need to give them what they need.
Treat your onboarding process like a top priority and nail it every time – you’ll thank yourself later.
5.) Make your sales process airtight and repeatable
This applies to any selling environment, be it in-office or remote, but is especially important with a dispersed team.
Your process needs to be defined, mapped out, documented, and (here’s the big one) EXECUTED ON. As in, the reps need to be ON PROCESS.
You simply cannot have everyone doing different things. It will compromise your data and your ability to glean insights. It will prevent you from forecasting correctly, which will prevent you from planning correctly, which will prevent you from budgeting correctly, all of which will prevent you from scaling and growing, etc. The list goes on and on.
The problems caused by a poorly defined and/or poorly executed sales process could have a post all on their own.
This doesn’t mean that your reps can’t try different tactics or strategies within the framework of the process. In fact, having a strong process in place is what will allow you to identify what people are doing that is working and synthesize it with the team, so that it then becomes a part of the process going forward!
Take the time and focus to create a sales process, with the goal of creating something that you could hand to anyone on day 1 and they would be able to understand and execute on it immediately. This should be your guiding principle for all your playbooks, which the sales process is inherently a part of.
Similar to the onboarding process, you just aren’t afforded the same room for errors here that you otherwise would be.
Lock in your process and do what it takes to make it airtight and repeatable. This is nonnegotiable.
6.) Get in the trenches with your people
As leaders, we think often on the answers to any number of questions.
What’s the best way to train someone on how to do something correctly? What’s the best way to lead? To inspire? To motivate? To build trust and rapport?
The answer to these and so many others is simple:
Get your hands dirty and get in the trenches with them, leading shoulder to shoulder.
If your team is on the phones, you need to be on the phones too. If your team runs demos, you need to run demos too. Whatever it may be, from prospecting to closing, you need to be right there with your people leading them from where they are, and they need to see and hear you doing it.
When I first became a leader, one of the things that helped me the most was that I was promoted from the role I was leading, where I had been the top performer, so I came into the role as a leader knowing exactly how to execute as a rep – and with a proven pedigree and the credibility that comes with it. Any tactical or strategic direction I gave was more easily received having come from someone who had a proven track record of success in the role.
Here’s the kicker though – while it is certainly helpful to be one the best at the role when showing others how to do it, it isn’t actually necessary.
You can still be just as effective from the trenches even if your reps are better than you. Ideally, they would be!
What is most important is that they feel you are there with them, supporting them, and showing that you are willing to put in the hard work alongside them and be vulnerable in the process. This is what ultimately builds trust and respect, which are two pillars of a healthy working relationship dynamic.
Approach this with an overzealous nature to compensate for what is lost by not being in the same room together.
Your reps will respond accordingly.
7.) Check in One on One often
One on Ones, when done correctly, are among the most beneficial operating mechanisms a leader has at their disposal.
A leader should always have time carved out weekly, at minimum, to meet with each person one on one with a set schedule, cadence, and formal process that has clear objectives and structure.
When working remote, it is critical that you check in One on One informally as well, and do so often.
This is a prime example of something that otherwise happens organically when in the same office.
Among the best benefits of being in-office is the ability to ‘check the pulse’ of a person – to feel their energy, to look them in the eyes and see where they’re at in a given moment.
Being the experienced leader that you are, you know that mental health is a major component of success and general well-being, and you know that with remote work comes the risk of feelings of isolation and loneliness, especially with socially oriented people.
Check in with your people informally throughout the week to see how they are, send words of encouragement, thank them for their impact, etc. – whatever you deem appropriate. Just make sure you keep it informal and supportive.
Pro tip: To prevent things from slipping through the cracks, schedule dedicated time for just this. It is too important to let fall by the wayside, and too easy to forget if not scheduled.
8.) Meet as a team regularly
In the same vein as One on Ones, team meetings can be incredibly useful or a complete waste of time – it all depends on how they’re executed.
You want to have daily virtual standups on the books to connect with the team to start the day, as well as a formal time set for the team to meet weekly.
Treat the standups as more of an informal chance to connect, while still using the time to cover important topics when needed. The formal team meetings should follow a set schedule, cadence, and form, with defined objectives.
Keep them both short and crisp, a meeting does not need to go longer than is necessary. Nowhere is it written that you must use the full 30 minutes you have scheduled. Accomplish what you need to and give people the time back if you can.
The idea is to connect, communicate, check the pulse and energy of the team, give clear direction, throw in some humor/encouragement/motivation/insight or whatever is needed, and get to it.
9.) Eliminate nonessential operating mechanisms
I recognize the irony in placing this directly after telling you to meet with your people and team multiple times a week – but in a remote environment, those opportunities to connect are 100% ESSENTIAL.
Many operating mechanisms, however, are not.
In today’s world, especially in tech, meeting overload can quickly become a vicious beast that will kill your production.
Tame this beast with ruthless intent and protect your people from it at all costs.
One of the biggest threats to engagement and overall employee experience is when people consistently feel like what they are doing is a ‘waste of time’, or even worse, preventing them from doing their job.
Approach every operating mechanism from this lense, pausing to ensure that the purpose has a direct impact on moving the needle forward, and is thus useful and worthy of occurring.
Additionally, spot check that in addition to being useful, it is something that warrants a meeting. Meaning ask yourself, “Could this be an email?” If you don’t have a clear reason why it can’t be, it probably is ok to just send a message rather than meet.
Pro tip: Start each meeting by stating the meeting’s defined objectives. For example, “The purpose of this meeting is to accomplish XYZ…”. If you can’t clearly define the objective of a meeting, cancel it.
10.) Get your KPIs and Metrics locked in
This goes hand in hand with your airtight sales process.
You want to be sure that the metrics you are tracking are defined, accurate, and easily visible across the team at any time.
This is activity, progress, pipeline, and bookings, primarily.
Specific to remote, you want to ensure you have an instance where the team is locked into each individual’s production as well as the team as a whole, and that it is surfaced multiple times throughout the day.
We used a team slack room to update throughout the day as a quick and easy approach.
Schedule this to ensure it is executed, or even better delegate it – or even BETTER, automate it.
You need to be in the details of the data consistently so that you know what levers to pull and when to pull them.
Part of being an effective leader is being able to look at the KPIs and see what is working, what isn’t, where areas for opportunity are, and then communicating your findings effectively so that everyone on the team knows exactly what to do and production improves over time as a result.
11.) Get the right tools and use them correctly
In any sales instance, there are your bread and butter tools that are must-haves: hardware, CRM, prospecting tool, conversational intelligence, forecasting, messaging, etc.
In a remote sales instance, you have those PLUS the must-haves for remote work.
The key takeaway here is to not just have the right tools, but to actually USE them the correct way so that you get the most value out of them.
Too often organizations spend a ton of money on fancy software designed to drive production only to find them too hard to implement, too cumbersome to use, and too easy to forget about.
Make sure when vetting out new tools to add to the tech stack that you are cognizant of the total picture, not just the dream a salesperson is spinning you. How will it be implemented? How will the team be trained on it? How will it fit into our current process? Make sure these questions are answered before pulling the trigger.
12.) Go the extra mile and put together team events
You should be meeting in person with your team multiple times a year, if possible.
This may take a little bit of doing on your part depending on your organization’s budgeting around such events and overall sentiment towards the idea, however it is well worth the effort.
Giving people that extra time and space to connect can make a huge difference. There’s a reason why so many top organizations have Sales Kickoffs to start their years – because they work!
Explore the different ways you can replicate that same energy on a smaller scale on a more frequent cadence to ensure remote fatigue never gets the best of your team.
13.) Feedback makes the world go round
Feedback, both giving and receiving, will be the thing that separates you and your team from the pack, turning good to great when done effectively.
On the contrary, if done poorly it will break your organization and condemn you to perpetual mediocrity (at best).
Working remotely only amplifies the impact and importance of feedback on both ends of the spectrum.
As a leader, you MUST set the standard for giving and receiving effective feedback. Make no mistake about it – this is a skill. And like any skill, it must be developed over time via consistent practice. So practice giving feedback often and consciously give your team the opportunity to provide feedback to you as well.
It could end up being the difference that allows you to acheive greatness.
Bonus: Tips for staying connected with your remote sales team
- Use text when appropriate. This is a great way to make the connection feel more personal. Note: Do not use text unless certain it is ok with the person and do not text off hour.
- Work in fun games at virtual happy hours to get to know one another on a personal level.
- Delegate your operating mechanisms to be led by members of the team. It will increase their level of ownership and strengthen your connection with each other.
- Send them helpful and encouraging things you come across. Even better if it is something out of the blue or unexpected.
- Send them gifts to show your appreciation. Even something small goes a long way.
The future of remote sales teams
In a world of uncertainty, this I can tell you for sure: Remote work is here to stay.
The sudden shift in the work environment that came as a result of the pandemic opened people’s eyes to new possibilities and normalized what was previously still very rare.
People are now excited by the prospect of not having to spend hours each day commuting, spending more time with their loved ones, and the increase in overall wellbeing that comes with being able to work from home.
And, just like for employers, remote work has opened up a wealth of new opportunities for people looking for their next career move who are now no longer limited to just what is in their area.
The battle to attract and retain the best talent has increased dramatically, in large part because of this.
It is for this reason, if nothing else, that the future of remote work is set in stone – most companies simply cannot compete without offering it.
Given your newfound knowledge of how to manage a remote team effectively, you are among those that can.
As always, I appreciate you stopping by.
Until next time,
Dan
