Advice for Managing a Remote Sales Team

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I lead the Sales Development team for Aircall in North America, and I love the energy that comes with working in a team environment. Collaboration, camaraderie, and competition are inherent to the process.

But like most sales leaders, the current global health circumstances related to Covid-19 mean that my team has needed to adapt and move forward in a measured and clearheaded way.

My career has included a sustained period where I was working in virtual positions and leading a remote sales team. Before I entered the SaaS world, I was an outside sales rep for Yellow Pages and advanced into a sales manager role. I experienced three solid years of working remotely without an office space or a traditional sales team environment.

While the situation was noticeably different, in many ways I’ve been able to pull out my old playbook to make sure my team today is managed in a thoughtful and productive manner.

If anything, I think my team is stronger than ever. We’ve been lucky to see consistent growth and meetings-set, but we are mindful to do so in a way that helps others through a really difficult time. As the new “normal” develops, best practices will need to change.

Here are a few recommendations for managing your remote sales team.

Set KPIs and clear expectations for remote workers

What are the expectations you have for your team? What expectations do you have for yourself?

In the modern sales environment, particularly in software and SaaS, we can tend to be office heavy. Our processes for communication or target setting aren’t necessarily prepared for remote work. Now, this culture needs to shift.

If your sales team likes working in an office, there’s a reason for that. As a sales manager, you need to recognize the core components of this mentality and do your best to replicate or artificially create this environment remotely.

A remote workforce still wants a sense of camaraderie, belonging, and accountability. They thrive in group/social settings. On the management side, it’s easy to hold people accountable to metrics and give coaching feedback when you’re sitting in the next row over, but when working remotely, there needs to be a more mindful eye.

One key piece of advice I’ve been giving to other sales leaders is to literally write out a specific go to market plan for a remote environment. What is expected of your individual contributors on the day-to-day? What do you require from your SDRs and AEs in terms of hard numbers, and what are the KPIs that you look at every single day to determine success or failure?

The first step is to put everything out on the table and distribute these ideas to your team. Stay transparent and keep everyone in the loop, but keep in mind that a transition from in-person to fully remote will be more natural for some of your reps than others. A learning curve is expected, and it’s your job as a sales leader to provide the individual attention where it’s needed.

Keeping sales representative accountable when working remotely

Theoretically, when working at home, you should have fewer distractions and experience more success. This is possible for all your teams, but it will take a larger-than-normal effort on management’s end to check in with individual contributors and ensure everything is on track.

I told my team the other day, “You may think some of my questions are micromanaging, but you know me well enough to know that’s not how I operate. But you should know that I’m going to ask you questions you might find difficult to answer.”

More so than usual, I’m asking about the specifics of my SDRs’ business. I want more details about the deals they’re setting up, and I want to know specifics. How many sales calls did you make yesterday? How many are you making today? If I ask you a question about your numbers, you should know. I need more employee engagement

My sales people need to be business owners more than ever. They are the startup in a closet that’s just launching. They need to operate as the CEOs of that startup. You have to hold yourself accountable and take successes personally.

Regular check-ins are vital for remote teams

While everyone needs to own their metrics as if they’re personally trying to raise a round of venture capital, we’re still a team. As a manager, you have to be even more dedicated to giving the group — and individuals — a solid chunk of your time.

Team check-ins

For starters, I’m conducting 9 AM and 4 PM Zoom meetings with my entire team. This is a carry-over tactic from our onsite playbook. Whereas we’d normally huddle around a conference table, now we’re sitting in front of our MacBook cameras.

And the cameras are on. As a manager, you need to see that everyone is present and paying attention. Just like an in person meeting, you need to be able to gauge the energy levels and rally the troops if needed.

For instance, our 9 AM team meetings usually start with some music. Something corny and energetic to set the tone. I played bagpipes on St. Patrick’s day. Keep it fun.

Individual check-ins

Even more important than boosting team morale and participation is encouraging your remote workers to do their best.

Make it a point to keep all one-to-one appointments. Furthermore, carve out half of each day to go deep into a single sales rep’s business. During this block, I’ll read all their emails. I’ll listen to the call recordings of any “calls-of-substance” they’ve had, and I’ll provide coaching feedback and actionable recommendations.

This process takes about 4 hours, and it’s not something I would do if we were in the office. Under normal circumstances, I’d have a 1 hour floor review with each rep once per week and let them get back to their day, but in a completely remote work scenario, there needs to be this added level of accountability.

There’s a thin line to walk, but this process doesn’t mean micromanaging. After a 1:1 to go over what I discovered, I trust my remote sales reps will get back to business. They know they’re responsible for implementing any changes or strategies we discuss, and it’s the manager’s obligation to not hover unnecessarily.

Keeping a regular schedule in a remote work environment

You wake up at a certain time to go to work. Even though they’re saving commute time, I’m encouraging my team to continue waking up at the same time everyday. Keep the rhythm. Keep the habit. This is important, because it keeps your body and mind in the same pattern of productivity and work.

You don’t need to use your “commute” to do more work. This time becomes yours in a way that wasn’t possible before. Get a work out in. Read the news or a good book. Have conversations with loved ones. Take advantage of this time to create a healthy work-life balance.

Similarly, I’d prefer that my SDRs get dressed for the day as if they’re coming into the office. When you put “outside” clothes on, you’re putting your professional head on — starting your brain.

If you decide to stay in pajamas all day, you never leave the sleepy bed-state. Just because you’re working from home doesn’t mean it’s a home environment. You have to create the work environment artificially at first until it becomes a habit.

A special note on competition vs. social awareness

Sales, to a certain extent, is inherently competitive. It’s why we create numerical goals for individual reps, and it’s why results are updated on a team scoreboard as they come in.

In a remote environment, this urgency and competitive spirit needs to be maintained. We do this through various motivating factors, like competitions and with prizes, etc.

However (and I’ll update this section when the global circumstances change), it’s important to remember that we’re going through a very difficult time as a society right now. The Covid-19 pandemic has upended business performance and lives in general. People are worried and people are scared.

So while competition is still important for attaining targets, it’s important to remind ourselves that business has in many ways become less of a life-priority. In a sense, corporate competition — as a whole — has lost some of its appeal.

As salespeople, we have to remember — even though it’s often dismissed as cliche — that we aim to help our clients. We want to see them succeed in business and in life. So please, continue your outreach at the same volume and with the same passion as before, but be aware of the delicate situation we’re in.

Ask how your prospects are doing, but moreover, avoid gaffs that make you seem ignorant to the world around you. Don’t ask “Have you received the gift I sent you?” when nobody’s going into the office. Consider skipping or editing the emails in your cadence that mention live events or setting up an in-person meeting. Mention the difficulties of scheduling and family life when trying to arrange demos and payment processing.

A few final thoughts

Remote work is not sustainable for a long period of time if it’s not fun. In many ways, it’s a company’s responsibility to keep the remote employees engaged, but it’s easier for individual contributors to recognize what they need to stay focused.

Personally, I can’t work in an environment without background noise. I’m a creature of habit, and a decade in the sales profession has made me crave the sound of human voices. Knowing this, I have a second computer next to me that plays movies in the background all day. I know this wouldn’t work for a lot of people, but I also know how my brain works. If I had to sit alone in a quiet room all day I’d go crazy.

But beyond the circumstances that brought us to this point, I’m interested to see how this period of remote work changes our perceptions toward traditional work environments. The advice I’ve provided is a start, but many sales managers and directors will find new and innovative ways to keep their teams together while they’re apart. What tools will they use? Does it open up remote hiring possibilities? How will sustained remote work influence the new hire onboarding processes?

I’m still learning with everyone else. Stay safe and stay healthy.

Published on March 24, 2020.