How to manage a remote sales team

Remote working has suddenly become the new normal, for now, which has thrown all of us a whole new set of challenges when it comes to managing our sales teams.

There’s no getting around it. There are real trade-offs in going remote, almost all of which revolve around the simple fact that you’re not in the same room together.

When you’re in an office, a lot of things happen by default without you really having to think about or plan for them. When you’re in the same room, you can automatically:

• Overhear sales calls

• Celebrate a win together

• Get a feel for who’s productive and who’s stuck

• Offer ad-hoc coaching and mentoring

• Join a call, demo, or meeting at a moment’s notice

• Have a feel for your market just from the banter of your reps

These are the things you miss the most when you go remote, and at first, it can seem hard to replace them. We know this firsthand because over four years ago, Qwilr started building a remote go-to-market team across sales, marketing, success, and support.

In the early days, we really felt the impact of not being in the same room, and at times, we struggled with feelings of helplessness (on both sides), mistrust, lack of clarity as to what was important, low morale, and more.

But we got through it, tackling each challenge and creating new approaches that led to an even more productive and harmonious remote team than we ever could have imagined.

We learned that working remotely can be incredibly powerful, but it definitely requires a different approach. Here are six tips we’ve learned from our journey — I hope they’re helpful during this time of transition.

1. Get the communication flowing

The golden rule here is to set up strict communication routines, then stick to them.

After trial and error, we have a system that works, which is anchored by regular stand ups. Your whole team must do two things to make these effective:

First, write an email to the rest of the sales team detailing the following:

✨ A. Activity: How many calls/ emails / demos / proposals (whatever matters to you). This must now include ride-alongs (see below)

✨ B. Closed Won: Highlight any deals won

✨ C. Pipeline: Total value, as well as total closed vs. quota

✨ D. Their one focus for today (or this week)

✨ E. Their one focus yesterday (or last week)

✨ F. Stuck / Help: Anything blocking them?

Second, have a very short meeting where the team goes over points D, E, and F from their email. D and E are about accountability, and F is about finding solutions to help them move forward with a deal.

These calls can be daily, twice weekly, or weekly — whatever works best for you. Those with faster sales cycles should have a higher frequency, but generally I’d encourage you to start this with as much contact as you can handle and walk it back from there. Keep them under 60 minutes, or under 30 if you’re doing them daily.

While this is something even colocated teams would benefit from, it’s even more useful for remote ones — it really helps keep the team engaged with each other and with you. It helps you stay up on who is thriving and who is struggling, so you can leave those who are doing well alone and get more involved with whoever needs help.

On top of that, it provides some moments for celebration of wins, as well as problem solving and sharing of advice. And as a bonus, it encourages a bit of friendly competition between reps who see their colleagues’ numbers so publicly.

2. Get “in the room” with ride-alongs and call recordings

You don’t have to be in person to listen in on sales calls. The technology is there to allow us to join a sales call or listen back to it after the event. Use it!

As a manager, adding this discipline to your routine is incredibly powerful for you and your team. You can pick up the general vibe from customers, learn what their (new) objections are, and hear how your reps are responding. This brings the opportunity for real-time feedback, and adjusting the sales pitch on a daily basis.

It also provides a space for your team to do ride-alongs with each other on a regular basis, and this peer-based mentoring is great for both the mentor and the mentee.

In our experience, the best ride-along structure is:

• The rep and rider meet ~15 minutes before the call and go over context for the deal, the primary goal for the call, and anything in particular the rep is looking to improve upon.

• The rep leads the call. The rider can always jump in to help if it’s really needed, but the purpose is to be a rider, not a backseat driver. The rider should take plenty of notes on what’s going well, what could be better, and what next steps might look like.

• After the call, both meet for another 15-30 minutes to chat. The rider shares their feedback — both good and bad. It’s important that the rider tries to share some relevant experience from other calls or deals to build credibility, instead of blindly offering advice. Experience always trumps advice.

• The rep and the rider review the goal and next steps for the deal.

At Qwilr, we use Zoom for our customer calls, which makes it easy to record a call (with your customers permission!) or to invite your colleague along. We also use the call recording feature in HubSpot’s CRM.

We even have a nice little Slackbot built via Zapier that posts new recordings to a channel that people can review later, which is especially encouraged if they got some interesting product or business feedback.

3. Find ways to be social

Everyone needs a moment to banter in any business cycle, especially salespeople who are on the phone all day sometimes just need to reset by connecting with colleagues.  These connections are even more importantly during unprecedented times like this.

For teams in offices, socialization happens relatively organically as people run into one another in the hallways and gather for meals. For remote teams, you need to recreate those hallway moments using digital channels.

• Set up some non-work focused Slack channels based on the interests of your team — some of our favorites are #aww (pets!), #music, #my-kitchen-rules and, until recently, #nba

• Use tools like Donut to organize randomly assigned catch ups

• Try Zoom rooms that anyone can join for regular watercooler sessions

These practices have brought a genuine camaraderie and community spirit to the Qwilr team, making us stronger and helping us through the challenges currently at hand.

4. Embrace (and trust) the numbers

In an office, you get cues about how people are doing based on your impromptu conversations and by overhearing their calls. With remote teams, you don’t get to read the room quite the same way.

Remote teams, by nature, are inherently more focused on output. Not how much time people are spending in their seats, not on how they sound on the phone, but on what they’re actually doing.

That’s why clear and measurable goals, while a pillar for managing any successful team, become even more important for remote ones. And luckily, one of the great things about sales is that it’s relatively easy to measure.

That said, there are tons of different ways to measure sales output. Take your time to choose a focused set of metrics that really matter to you. Consider letting your team contribute their opinion about what’s most important — this will help you get people on board and diligently working on their numbers.

Picking the metrics is only the first step, though. Perhaps the most important part is your follow-through on checking in on them regularly. That way, you stay on top of how everyone is doing and set yourself up to take action accordingly.

It helps to set up systems that make this easy on yourself. We use HubSpot to quickly produce all our reports, and the regular sales team emails I mentioned earlier are a really good way to keep a rhythm on it all.

Side note: Obviously, we’re living through unprecedented times. Your team is going to find it very hard to perform at their best for a wide variety of reasons, and it’s currently an incredibly challenging sales environment for many companies. Try to take that into account with your numbers, and make sure that you’re spending more time on team morale, too.

5. Don’t disrupt the flow: asynchronous updates

The real secret to remote work is getting better at working asynchronously. We’ve all heard that before, but how do you do it well? In our experience, that means:

• Build in a lot of regular little moments for communication but try not to make them meetings. Allow your team to do their jobs uninterrupted for the vast majority of the day, then check in with updates via Loom and other tools so reps can review when they have a break. Remote working should never mean a calendar full of internal meetings in place of talking to customers and prospects.

• Make written updates efficient. We’re big fans of creating fast written updates, and we use our very own Qwilr product to great effect for internal communications. It forces us to clarify our own thoughts, progress, blockers, and gives other team members an easy reference to check back on, 24/7. It also allows us to have up-to-date docs that can handle video updates too.

• Don’t expect immediate responses. This one needs to come from the top. Make it clear that when you email or message someone, most of the time they should just respond when they have a moment. You would never walk into a sales meeting and force your rep to answer a question immediately, so don’t do that to them now when they might be back-to-back with calls.

• Shared calendars are your friend. At Qwilr, everyone can see one another’s calendars. Reps often block out large chunks of every day to make sure they have enough time to do all of their various tasks, as well as leaving lots of blank spots for calls to be booked, often automatically through Calendly. Work hard to respect your team’s calendars!

A word of warning for always-on communications: Tools like Slack or Microsoft Teams can be wonderful, but they can also become distraction engines. Work with your team to make sure that they have plenty of focus time to do work.

6. Improve your team’s tools

When everyone is in the same room, it’s amazing at how little some processes matter, especially for smaller teams. You can really get away with a lot.

That’s not the case with remote. You need a good CRM that’s both well set up and well managed by your team. Sloppiness here hurts twice as much when you’re remote, because it’s even more unclear what data is accurate.

The same is true for your sales and marketing collateral. It can be easy for some reps to be left out of the loop — leading them to send out old, ugly, off-brand materials that actively damage your prospects’ perception of your company.

Qwilr can help dramatically improve this by serving as the library that holds all the most up-to-date and approved assets, all while being deeply embedded into your CRM so your source of truth is always accurate.

At the end of the day, be creative — this is not a “copy and paste: exercise, and you’ll need to experiment to find the things that work best for your team.

Remote working changes many things, but it doesn’t have to change the productivity and energy of your sales team. We’ve refined our way of working so much over the past four years, and while we’re not perfect, the learnings we’ve gathered along the way have meant we‘re the same high-octane sales engine we would be if we were all sitting in the same room.

Good luck over the coming months!