How to Manage a High-Performance Remote Sales Team

If you truly value your team, remain flexible, work together and communicate clearly, you’ll get through any period of uncertainty — including a global pandemic.

Written by David Stout
Published on Nov. 11, 2020
How to Manage a High-Performance Remote Sales Team
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Over the years, I’ve learned a thing or two about managing high-performance remote sales teams. In this time of heightened uncertainty, however, I am seeing a few important deviations from the norm. Schedules are more unpredictable than usual. Both my team and customers have children at home. Being unable to meet face-to-face makes connecting with the team — and with customers — harder. Market fluctuations affect buying decisions, and the many last-minute buying decisions cause increased stress on sales.

Despite this, the core principles of supporting and leading a remote team don’t change. If anything, you have to lean into your values more when uncertainty increases.

Core Principles for Managing a Remote Sales Team

  • Lead with compassion.
  • Communicate clearly.
  • Trust your people.
  • Nurture teamwork.
  • Promote friendly — not cutthroat — competition.
  • Implement smart processes.



As a manager, I make it a policy to lead from the front but to do so with compassion. Family comes first — always. With school schedules being in flux, it is important to maintain flexibility around job responsibilities and understand that employees may not always be able to work core business hours. I am always ready to jump in when a teammate needs extra support, whether that’s covering a sales call or helping execute a contract.

In times like these, I also stress that travel is completely optional. These policies aren’t just hot air. I model this behavior so my team feels valued and trusted when unexpected issues arise. As they say, if you talk the talk, you’ve got to walk the walk.

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Communication is essential to success in any environment, and that truth is only heightened in the current moment we’re living through. Be human and encourage your team to be comfortable with difficult conversations. I find daily stand-ups are helpful when checking my team’s temperature and ensuring we are clearly communicating. Being open and respectful of your team prevents a lot of headaches in the long run.



One thing that has helped me tremendously over the years is finding good people and trusting them to do their jobs. I have a history of hiring reps I’ve worked with in the past. I support them when they need help, but I never take over because I trust they will do everything they can to get the job done.

If someone on my team is struggling, I try to find out the underlying issue. Usually, something going on in their personal life has caused them to lose focus, and then their motivation slips. My goal is to help them mentally find peace and balance to get them back on track. This may be a sympathetic ear to vent, a couple days off, or maybe a project that is a change of pace. Reality is there are many ways to help the great person you hired get back on track, just have an honest conversation and understand what is going on so you can find a path forward together.

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Building a sense of camaraderie is important to any remote team. I encourage my team to work together to lift everyone up by promoting a culture of team success alongside individual success. While it’s great to be the No. 1 salesperson, it’s even better to be the No. 1 salesperson on the No. 1 team. I promote a culture where everyone is on the same team working toward the same goal.


Friendly Competition

Following on teamwork, our internal contests are friendly, not cutthroat. Competitions are great for building momentum — but only if they are fun and cooperative. For example, we recently had a contest where the prize was a kegerator. As part of the competition, we had daily stand-up meetings not just for tracking, but also for sharing ideas and promoting creativity. My team was able to cheer each other on while still competing with each other.


Smart Processes

One last but important piece of advice is to be smart with your time by having good processes in place. Whenever my team identifies a bottleneck, we work together to streamline the process. For example, at the end of the quarter when time was critical, we were getting bogged down with legal, so I began acting as the single point of contact between the reps and the legal team. I had daily stand-ups with legal to keep the process on track and avoid each rep spending time tracking things down. This freed up the reps’ time so they could sell, and legal had requests coming from only one person.


Every Quarter Is Now Year-End

In a typical year, our customers hold on to their budget until their year ends. This results in a hockey-stick sales curve, where the majority of deals are done at the end of the last quarter. Currently, we’re seeing a similar cycle, but on a quarterly basis, which is what I call the “Hockey Stick Sales Curve on Steroids.”

Customers are not putting off purchases until the end of the year; instead, they are waiting until the last two weeks of each quarter to make sure their business is doing well. Once they are sure their business is meeting expectations, they spend their budget before they lose it.

This change puts stress on my sales team. To support them, I remind sales that our customers’ procurement and legal teams are overloaded. Sales can help the customer stay organized and set timelines to create a sense of urgency on both sides to avoid delays. Remember, procurement wants to get this off their plate too — they just need to make sure they are fighting for the best possible solution. So dont play games!


How to Hire and Retain High-Performing Teammates

When hiring, there are two things I look for in a candidate: curiosity and chemistry.

Curiosity is the single most important quality when it comes to hiring. I look for someone with natural curiosity who strives to understand the how and why of a deal. Technology and product can be taught. Curiosity and asking the right questions cannot.

When it comes to chemistry, the candidate should reflect the team’s culture. I avoid candidates with negative attitudes. Same for candidates who are only in it for themselves. A self-centered person will not raise the team up.


Putting Your People First Ensures Everyone’s Success

The bottom line is that, if you value your team, remain flexible, work together, and communicate clearly, you’ll get through any period of uncertainty, including a global pandemic.

My team recently asked for an in-person QBR because they missed seeing each other face to face. I take this as a marker of high praise and success that they want to spend time together. We made this happen, while stressing that it was completely optional. In fact, several team members opted out; we supported them for their choice.

That’s because my focus is always on what’s best for my people. Communicating, listening, putting their needs first, and building a fun team is how I lead from the front with compassion. The results speak for themselves.

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