How to Manage A Remote Sales Team

joshua fedie and mickeli bedore remote call

Right now, sales teams all across the globe are going through a painful transition. Seemingly left behind them is the electricity and comradery of salesfloors and big conferences. In many companies, the response has been ad hoc with varying degrees of success. Hastily constructed desks, designating offices within homes with Post-its on closed doors, and virtual happy hours are trademarks of the temporarily remote sales team.

Whether a remote sales team is a temporary situation or you’re making the commitment, your reps need the right leadership and management to meet the unique challenges of remote work head-on.

For sales managers, it’s on their shoulders to initiate and maintain a digital transformation initiative seemingly overnight.

This post was written to help sales managers and their teams become more successful in their new remote environment.

We took a look at what successful teams are doing, what sales technology companies are recommending, and the trending stories to sort through the panic and pull out the best practices.


3 pillars of a successful remote sales team

  • Culture – how your people collaborate and connect
  • Management – direction and guidance
  • Technology – what your team uses to get ahead

In our search, we’ve noticed that there are some common themes that all remote sales teams need to consider.

We found that when it comes down to it, managing a remote sales team is really about three things: culture, management, and technology. We like to think of these as essential pillars of your remote sales strategy.

If you don’t get these three components right at first, it won’t be the end of the world, but if you ignore them for long enough it’ll be the end of you. Let’s avoid that!

Help define what remote sales culture should be

Focus on building trust

Early on, building a culture of trust between remote workers should be your primary concern. In remote environments, work conditions are obviously different but the unique challenges they present often bring out the worst traits in management.

Communication is key to building trust. The team will have to collectively adjust and find a balance with over-communication and staying efficient.

Harvard Business Review report demonstrated that people avoid helping others when they lack trust in their teammates or managers.

Managers are responsible for the change in the organization. During uncertainty looking for helpers in your organization can make a huge difference.

Instead of micromanaging, look to the helpers

Over at PandaDoc, they say, “There are certain skills and traits that translate better to remote work than others… Focus on those who demonstrate time management and organizational skills and are comfortable working autonomously from any time zone.”

In uncertain times people, especially those with more authority, often seek to exercise more control. Studies have shown that micromanagement is a recipe for disaster in remote work.


Negative effects of micromanagement on remote sales teams

  • Increased stress that more easily carries over into one’s personal life without spacial barriers
  • Feelings of helplessness
  • A rise job-insecurity
  • Fear-based decision making, survival mode
  • Fatigue from overwork
  • Employees become unmotivated and dependent on the direction

To avoid the negative impacts of micromanagement decide if you need to distribute your managerial tasks and empower your team to act more autonomously. A more flat and distributed team structure has been the most successful structure for remote work environments.

To decide who you can trust with the added responsibility of helping you lead the team, identify those who are personable, communicative, and flexible. They’ll make great leaders of remote teams.

Lead with empathy

If a remote sales setup is new to your company then without any doubt, there will be an adjustment period. In many ways, this is management’s make or break moment. They will be relied on to help their team members with this adjustment. If you identified who your natural helpers are on the team this is a great opportunity for them, and you.

Psychologists who’ve studied empathy say that empathy isn’t an immediate response.

“When assessing the world around us and our fellow humans, we use ourselves as a yardstick and tend to project our own emotional state onto others,” says Prof. Dr. Tania Singer in Psychology Today.

Managers need to check this impulse and instead lead with empathy.

Forbes recommends regular meetings with the team to open a dialog and seek to understand everyone’s remote working needs and resolve those early.

“You should also empower your staff to feed into and shape how your remote working culture can be improved. Invite staff to provide feedback to improve tools, platforms, and communication channels. Ask them to suggest initiatives to simplify and ease remote working,” says Forbes.

Be intentional about getting feedback early and pivot your strategy to accommodate the needs of your team. It’s more important that they have what they need to achieve their goals than executing your precise idea.

Again Forbes, “You will also give them a feeling of being able to shape their own remote working environment and that of their colleagues, which is enormously empowering for most people.”

As you and your remote sales team settle into the routine it’s important to reinforce a positive workplace culture. There’s a perception that you’ll need to work harder to do this in remote work environments but the truth is you need to work smarter.


Tips for managing a healthy remote culture

  • Calendar management: all meetings with agendas are on the calendar and visible for everyone
  • Make time for team get-togethers: virtual and in-person
  • Encourage and reward collaboration
  • Dedicate more time to enablement, training, and collaboration

Double down on winning management principles

Time is money

Managing remote reps is time-consuming but your time is one of the most precious resources for your team. A great remote sales team manager will be a wrecking ball to any silos that exist between remote reps.

Picture a salesfloor at an organization with several reps. They’re sitting near to each other, listening in on calls, getting a little competitive, and learning as a group. That’s not your sales team.

Remote sales managers facilitate collaboration and learning through leadership and managerial access.

As a remote sales manager, training and enablement should be your priority. To accelerate your impact, empower your more experienced reps and your helpers on the team to mentor and spread useful information.

Understand that you must make yourself available as much as possible. You are the center of connectivity and the link between every rep. Master the art of calendar management.

Ensure your team knows you’re available but do not place yourself as the only gatekeeper.

Open up

If your remote sales team is built on trusting relationships you should not have to worry about upping permissions. This goes back to culture. Remote sales floors need a different setup. Reps can’t just walk over to a desk and ask for guidance.

One of the best ways to scale learning at a remote organization is to open up the dialog to more than just celebrating wins.

Celebrate the fails too.

Here’s Gong.io, “It may sound crazy, but there are very real reasons you’d want to create an outlet for your remote sales team to share fumbles… The last thing you want is reps sitting on their hands when they need help. Sharing setbacks creates an atmosphere that encourages team members to share their difficulties.

Working from home can be unstimulating for those who didn’t choose to walk away from the heat of the sales floor. That’s where you can step in as a leader through coaching and enablement.

Like bucket of cold water, regular call reviews can bring new life to a reps day. They should be a way to spark discussion, share tips, and encourage collaboration.

Your team should embrace openness as a means of learning. Your tech should open up too.

Give your team more access within CRM and other sales tools. Make sure everyone on the team has visibility on what’s happening in deals. Establish a clear mandate on keeping opportunities and deals updated. Everyone needs to be on the same page. 

Keeping the information flowing is of great importance. Data should power decision making and your dashboard will be your rock to cling to if it gets rough.

If necessary, create a new reporting structure that reflects remote sales work and make sure that what you’re measuring is visibly tied to reporting outcomes.

Provide your team clarity upon performance and leverage data to reveal what’s happening at large to inspire collaboration and alignment.

Seek alignment

Over at Gong.io, they encourage managers to get to a point where meetings are focused on strategy.

“Getting information to flow in your team will allow you to start the week strong with *actual* pipeline reviews. Instead of getting caught up on what opportunities have been or haven’t been updated, you can spot at-risk deals and define the next best steps for those accounts,” says Gong.

Recently we had Scott Burns, CEO of Structural and who’s led multiple startups on the podcast. He shared his leadership style with us,

When I started, I really thought ideas mattered a lot. And I thought that it was important to do things the right way and my ideas were the way to make things work. With help, I evolved to a much more focused leadership style where my contribution is in alignment, always investing in alignment and understanding, even if it’s frustrating. It’d be easier to just say, do X, do Y, whatever. [Instead] let’s align and understand. So the idea gets better when I’m removed from it.

Scott Burns, CEO of Structural
The Founders’ Mentality

Focusing time on the ‘how’ is a slippery slope for managers. Ultimately it means less time executing and a fleeting sense of control.

Just like with micromanagement there can be the impulse to over-commit your team to your ideas and giving too much over to the process and the ‘how’ something gets done.

Remote work alignment and understanding of clear goals are priority number one. If your team is going remote then throughout the course of transition continue to make sure everyone is aligned on measurable goals, teams become more efficient, motivated, and successful.

Your team should know why it’s important to collaborate, to log information, and to share ideas. Equally as important, they should know what it feels like when it works.

Wins of any size are important. As a manager make sure there’s time to celebrate wins and give the floor to the winner to share the story that led to success.

The biggest win: hitting goals. Smaller wins are nailing expectations.

In addition to setting goals, managers should be crystal clear on setting clear expectations.

Set clear expectations

We’ve heard that expectations are not process. Rather, they’re results-oriented. Expectations should encourage sales employees to meet higher performance levels.

Here’s what they say at Pipedrive, “The benchmark should include sales objectives, specific online procedures when working on leads, and tips for managing time more efficiently.”

Expectations should also be an open the door for more communication and dialog around what happened, why, and what could have been done better.

Bring in technology to address gaps and get ahead

We are fortunate to live in a time in which there is a massive marketplace of technology companies looking to solve nearly every business problem. Remote workforces are powered by technology.

When the COVID-19 pandemic had grounded sales reps and cancelling conferences we wrote this post on the best technology for remote sales reps. We wanted reps to pick up new tools, even free ones, to bridge gaps in their performance.

That’s exactly what you should do on a regular basis. Seek to understand where your team is weak and see if there’s a technology solution to fill the gap so your team can focus on what they’re actually good at.


Best Tech for Remote Sales teams

  • Salesforce to keep your data
  • Google Suite for collaboration and file sharing
  • Slack to get quick answers and chat
  • Zoom to personalize meetings
  • Gong for call recording and analysis
  • Drift to chat with prospects in realtime
  • Databox for customized report cards
  • Trello to quickly keep track of tasks
  • Loom for visual storytelling and coaching
  • Vidyard for video messaging
  • Calendly to book meetings efficiently
  • SalesReach for delivery and customer experience

The team at Slack has written a lot about remote work, they’re an excellent resource. Here’s an excerpt from their manager’s manual for remote work they suggest, “A #team-random Slack channel for water cooler talk. This not only lightens the mood, but creates a shared culture too. If social chatter happens in your team’s work channel, clarify that conversations should stay on topic there, but banter is OK in #team-random.”

Whether you’re explaining a complex document or task or planning a team bonding event you should ask yourself, is there a better way to scale how I include members of the team.

We’ve found that simple video tools are the best ways to accelerate collaboration. Video messages give your team the power to rapidly share precise information and gather understanding.

You’ll be a better coach when people can hear your voice and see what you’re talking about. You’ll eliminate chances for miscommunication when you’re able to show someone what you’re thinking.

Sharing fails, the occasional #team-random post, and video coaching are great examples of what a lot of remote work technology is designed for, make us feel more connected.

As a manager, one of your biggest wins can be to simply make sure your team feels like they’re included in the excitement of the day-to-day sales floor.

Think about your remote sales technology stack carefully. You should select tools that bridge gaps and it’s easy to have tools overlap nowadays.

SHARE YOUR STORY: What are your remote sales management struggles and strategies?

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At SalesReach we’ve recently moved to an entirely remote office.

Many of our perceptions about remote work were wrong and we were surprised by what actually became a problem for us and what things didn’t end up mattering at all.

Hey, every sales team out there is different, we all have our quirks, right? Ours is relatively small and our CEO loves to sell. We’re not telling you what to do–just sharing what we’ve found.

Above all, this challenge presents a great opportunity for salespeople to get ahead of the trends. For some time, the nature of sales has been changing. Leading research has shown that customers expect their salesperson to demonstrate ‘flip on the fly’ behavior.

Sooner than expected more customers will expect salespeople to meet when and how the customer expects, to have an answer right away, and to leverage technology to offer more robust personalization and custom solutions. Remaining adaptable during this time will surely pay off in the long term.