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How to Build and Manage a Remote Sales Team Successfully

How to Build and Manage a Remote Sales Team Successfully

Anirban Banerjee
Anirban Banerjee
December 16, 2022
5 min read

Jack is meeting his friends after two long years post-pandemic. He never thought he’d be so glad to see their faces. Hugs, fist bumps, and slaps on the back all around. 

The hot topic? Remote working. They had never expected to work from the comfort of home. (So long, traffic!)

Jack tells the crew that his organization has been allowing him and his fellow sales reps to choose whether they would prefer to work in the office or remotely. Jack is loving remote work. He has drastically increased the number of customers he was dealing with. He can end one sales meeting and hop immediately into another at a completely different location. He is hitting sales quotas like never before. 

A normal day in Jack’s life - Hitting targets like a pro.

Nick, on the other hand, hates it! He says he can never quite figure the prospect’s reaction to his pitch.

“In-office was so much better!”, he grumbles.

How could the remote selling experience be so different for two equally capable sales reps?

As it turns out, Jack’s sales manager had created a remote sales strategy that took into account the challenges of remote sales meetings. Jack and his colleagues have a ton of new tools to ease the challenges of remote sales.

So, the big difference between Jack’s and Nick’s remote sales experiences was - the existence of a focused remote selling strategy or the lack of one. 

Well, that settles the discussion.

What is remote selling?

In remote sales, the playfield changes, but the game remains the same. You’re still going through the same old sales process, from prospecting to closing deals. But you’re communicating with the prospect using web conferencing instead of physical meetings. 

Is remote selling here to stay? 

If you’re thinking, “Well the pandemic is behind us and that means buh-bye remote selling,” you might want to think again. Businesses have tasted the revenue savings and time savings in remote sales, not to mention the fact that it does away with geographical barriers. 

No corporation worth its bottom line is going to let go that easily.  

By 2025, 80% of B2B sales interactions between suppliers and buyers will occur in digital channels, according to a study by Gartner.

It’s not just your employers; your prospects like it too!

Otherwise-hard-to-catch-hold of prospects digging remote meetings 

According to McKinsey, “70% of B2B decision makers say they are open to making new, fully self-serve, or remote purchases in excess of $50,000, and 27 percent would spend more than $500,000.” 

Benefits of remote selling 

Like Jack in our introductory analogy, lots of salespeople find remote work more productive. Not to mention that they enjoy the flexibility of working from anywhere. You also save time because instead of traveling from one meeting location to the other, you hop from one call to the next in seconds or minutes. 

You and your sales reps are also able to analyze customer interactions like never before. With the help of sales intelligence technology and virtual sales assistants, every interaction is a sea of data points ready to be stored, harnessed, and analyzed. Virtual interactions can be recorded, and you can use these recordings to provide personalized coaching. 

Prospects tend to prefer remote meetings because they can multitask and tune off if the salesperson is boring them. It’s also easier to end remote sales meetings. 

Corporations, as we mentioned earlier, incur lower costs in a remote set-up and might prefer it, provided the team is meeting their sales quotas. 

But to be fair, remote selling isn’t all rainbows and sunshine. It comes with a set of unique challenges - that you and other sales leaders need to overcome.

Challenges of remote selling

Here are some of the most common obstacles to success in remote sales: 

Keeping the prospect engaged 

Picture this: your prospect’s camera is off, and they get a text mid-way through your Zoom meeting. While they’re busy laughing at the meme they received (or sending a scathing reply to a colleague’s email), they missed every word you said during the best part of your sales pitch. 

What did you say?

Not having eyes on the prospect is a huge drawback. If you had met them in person, you would have paused your pitch as they responded to a text, or they might not have looked at their text in the first place because it might be perceived as rude. 

Lack of visual cues

When you meet face-to-face, you see a nod and know you’re doing well. A blank expression prompts any sales rep to try different words. Raised eyebrows might hint at wariness. But in a remote work environment, visual cues are lost. Salespeople have to figure out little things, like whether the prospect is taking a pause to speak or is waiting for you to explain yourself further.

Easy riddance (of the sales rep) 

Online sales meetings have more strongly defined endings. Earlier, when your sales reps went to face-to-face meetings, they might be able to hold on to the prospect until they are able to convince them to make a purchase, but today, it’s easy for a lead to cut you off saying that they have another video call scheduled.

Technological issues 

Slow or patchy internet or a bad microphone can completely change the output of your sales meetings - fortunately, this one, at least, is easily fixed.


Gear your remote sales team for success with these moves 

Be clear (maybe even repetitive) about sales goals

Micromanaging isn’t ever advisable, but sales leaders do need to manage to a deeper level with a remote sales team. Action items and goals that become obvious when you’re all under the same roof need to be vocalized and reiterated for a remote team. 

Your team, when you’re not giving them instructions 

Set clear expectations for day-to-day performance. 

Be present 

We’re not asking you to stalk your people, but you should continue to manage them. Hold regular check-ins with your salespeople to discuss their struggles and victories. You can keep in touch via Slack for the most part, but be sure to make your presence felt with face-to-face meetings by video conferencing from time to time. 

Tweak your hiring and onboarding processes

Hiring the right team, one sales rep at a time, is the key to building a successful remote sales team. An ace face-to-face sales rep who is motivated by the in-office buzz might not perform as well in a remote environment.

If you are a remote sales manager, asking a handful of focused questions will make it easier for you to imagine the candidate’s behavior in a virtual setting. Try these: 

  • How comfortable are you with remote selling?
  • Do you have past experience in remote selling?
  • What motivates you to focus on work every day at home?
  • Do you think the discovery process change in a remote work environment?
  • What projects have you completed under your own supervision - both professionally and personally?

Your onboarding process should be able to gear a remote workforce to hit the ground running. Get together a strong collection of sales pitch templates and recordings of highly successful calls for newbies to get an idea of what they’re going to be up against and how their colleagues deal with it.  

Get your remote workers to implement these tips

  1. Keep the intro sales pitch shorter
    It’s easy to lose track of thought on a sales call or in a video conference. Your remote salespeople are always running the risk of losing the attention of their prospects and missing out on the deal. 
They’re SO listening

To overcome this, set a norm for 6-10 minute long sales pitches that include visual aids and sharing a compelling story. More information can flow in later. 

  1. Turn on your webcam
    Putting your face (and your smile) into the conversation helps in building trust between the sales rep and the prospect. The prospect attaches the promises being made to a human rather than a brand name, and that’s easier to believe. It might prompt the prospect to turn on their own camera, which would make the sales meeting a lot easier for your sales rep. 
  1. Be an attentive and active listener
    Making someone feel heard empowers them to be candid about their concerns. Remind your sales reps to ask relevant follow-up questions and repeat what the prospect has said. This also helps to avoid assumptions and misunderstandings.

Provide remote sales training

A remote work environment might be a relatively new setting for your salesforce. Yes, it's two years old, but they might still struggle to adjust and perform in this “not all that new anymore normal.” Sales training with a special focus on remote settings can help your sales rep leverage their skills in the new playfield. 

Avoid the kind of sales training that includes a collection of randomly chosen motivational quotes and a catchy slide deck of generic “best practices”. 

Your team when you spew cliches. 

Instead, try sales training that provides specific pointers on things that the team - or a specific rep - does well. You should also talk about practices that need improvement, but it's always best to tackle criticism privately, in individual meetings. Play recordings of cold calls or pitches, or negotiations that went especially well. Cite an example (without naming anyone) of a sales call that went badly and tell your reps how to avoid such a situation. 

Track sales metrics

To track your remote worker’s sales performance, you need to track and analyze overall sales process metrics. 

You can use the metrics such as sales pipeline coverage and opportunities, participation rate, win rates, sales quota attainment, meetings booked, and volume sales calls. 

Automate your tasks with Wingman

Managing a team through a screen can be challenging. Let Wingman help you create an efficient remote office space that works to achieve your sales goals. 

Wingman is an AI-powered tool that helps you build and manage your remote sales team better with call success metrics, at-risk deal alerts, and AI-powered call recordings, summaries, and transcripts. 

At-risk deal alerts tell you when your reps need you, even when they’re not right in front of you so that you can hop on to their calls and play superhero. Success metrics tell you who your star players are and also encourage reps to bring their very best to the game. Call recordings help you zero in on exactly where your reps need coaching.

Sales managers who use Wingman zeroing on problems like dudes.

Meanwhile, your reps can focus on being attentive to the prospect rather than tedious note-taking, and this helps them make a better impression. Wingman also provides live, contextual cues to sales reps during their sales calls,  supporting them when you cannot.

Help your remote sales team achieve everything you know it's capable of. Get them a Wingman. See how Wingman helps you level up your game hands-on. Try a free demo today! 

Real-time sales coaching software that helps your team win deals with confidence

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