6 steps to leading and managing a remote sales team

Remote selling is a new concept for most leaders that can lead to a new set of challenges. Here are six steps to managing a remote sales team.
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Managing a remote sales team for the first time? Feeling out of depth and unsure how to begin? 😫

You’re not alone. Gartner’s The Future of Sales report predicts that by 2025, 80% of B2B sales interactions between suppliers and buyers will occur in digital channels. While progress is always good news, having to make transitions that used to take years to plan has had and still has companies floundering.

In this piece, we give you a behind-the-scenes look at how we built and grew our remote-first sales team and the lessons we learned along the way. 

First, let’s get you familiar with the challenges you might face when you manage a remote sales team before we jump to the solutions.

Challenges of remote sales team management

challenges of managing a remote sales team

Remote work can be the "good life."

But remote sales team management isn't a cakewalk. First off, you have to deal with...


Harvard Business Review called poor internal communications the silent killer of great teams

In the post-pandemic workplace, effective workplace communication is crucial. 

In-office means you can pop into someone’s office to get an update or clarify issues. A remote working environment needs a more deliberate approach. Get it wrong, and communication is inconsistent and misunderstood.

Poor communication = a decline in productivity.

When you manage a remote sales team, it’s important to communicate consistently, clearly, and continually. This helps to avoid confusion, builds better relationships, and keeps everyone on the same page.

Lack of standard workflows

Your remote sales team is like an army platoon bypassing enemy frontline strongpoints as they approach their target. 

You want to make sure everyone gets to the target even if they are approaching from different angles. If there’s no tactical plan, you don’t just miss your targets; you are also unable to protect yourselves. 

Having a structure ensures the team knows the tactical way to keep connecting with prospects and closing deals. It also guarantees you identify problems in the workflow before it impacts the company’s revenue.

Building out and communicating a clear strategy and workflow for your team to follow is a major part of remote sales team management.

Mental health & well-being

Hinge Health’s survey on remote workers in the US showed that 73% of respondents’ stress, anxiety, and depression have worsened or is a new experience they’re feeling since remote work due to COVID-19.

Salespeople are anecdotally known to thrive on in-person interactions. 

The pressure of the job plus the lack of in-person meetings can be detrimental to the mental health and well-being of first-time remote sales reps.

Limited remote selling resources

This challenge is two-fold. 

First, you might struggle to find the right tech stack that empowers your team to do their best work. Which often means testing many tools until you find the ones that meet your needs. 

And second, most remote sales playbooks are CTRL + V of traditional sales playbooks.

Maybe you are already familiar with these challenges and are here to improve or figure out a solution. 

We’ve got you.‍

6 steps to leading and managing a remote sales team effectively

UserGems has always been a remote-first company. 

So, we’ve had to build and manage a remote sales team from the start. Here are a few things that set us on the path to success.

Hire the right people

Christian Kletzl, UserGems’ CEO and co-founder, believes that hiring the right people is critical to building a successful remote sales team. And we agree 😀🚀 

Ross Rich, CEO, and founder of Accord adds, “[For early-stage startups], it’s less about the role and more about the person you hire.” While hiring right is usually a matter of luck, knowing what skills your company needs at the time can also assist in making the right choice. 

If you're a sales manager building out your remote sales team for the first time, look out for generalists rather than specialists until you have a firmer view of what you need. For example, our first sales hires were Account Executives (AE) but we looked out for AEs who were also skilled at closing. 

“To give you an idea, an Account Executive is focused on being the closer and a Sales Development Rep is focused on being the hunter. But when hiring an AE, I don't think it's okay to only be focused on closing,” Christian explains. 

“I look out for someone who thinks ‘Yes, I have an SDR helping me but I'm able to take my destiny into my own hands.’ If I have to choose between a good closer and a closer who can also hunt, I'll take the latter,” he continues.

When your remote sales team is made of people who have the right skill set and love what they do, motivating them becomes easier.

Remote selling tip

Establish clear expectations

In a remote setting, you can’t always reach out to someone in real-time or have an eye on their activities.

So, it’s essential that everyone is working towards the same goals. As a sales manager, you want your sales team to close. But they might be so focused on the hunting aspect, they don’t have enough time to close. 

Set clear expectations that nudge the team on to the ultimate goal of every sales prospecting motion - the close

Make sure your team has the right remote sales training

The buying behavior of B2B buyers has changed in recent times, and the pandemic only accelerated it. 

As Gartner reports, 33% of all buyers desire a seller-free sales experience. What does this mean for sales teams everywhere? Old sales playbooks need revamping. 

Reps must learn new sales motions that are a fit for a virtual sales process to succeed.

Build processes, templates, and workflows for running effective check-ins

Check-ins help you stay on top of the pulse of your sales team. 

It allows you to identify issues early, provide support and connect with your team. Here’s how we conduct our sales check-ins and quota review meetings at UserGems.

At the quantitative stage, we track

  • Deals in each stage (compared to the rest of the team)
  • Total expected value in the pipeline
  • Deals at bottom of the funnel
  • Expected value to close this & next month
  • Close rate
  • Number of activities (emails & calls)


Our qualitative review process looks like this:

1. Focus on the bottom of the funnel first. Go through everything that’s in trial or negotiation and especially focus on: 

  • Are there any deals in which I can be uniquely helpful? 
  • Where can I contact the decision-maker or someone else in the team to drive the deal forward?

2. Next, we have a report for deals without stage movement in the last 30 days. This shows which are most likely stuck and need to be discussed. Also, the idea is to help the AE think through the deal from an outsider's perspective:

  • When’s the next meeting? When was the last meeting? What’s the next step?
  • Where can I contact the decision-maker or someone else in the team to drive the deal forward?
  • If no clear next step, let’s go back to the basics. What’s their pain point? Why are they seeking us out? What has happened so far?
  • Which stakeholders are involved? Who’s the decision-maker?
  • What’s their timeline? Last communication?
  • Have we heard any objections? What competitors are they using/evaluating?

Often, we don’t have time for all deals, so we focus on:  

  • Regardless of the stage, are there any high-priority deals? Any deals where executive support could help?

3. Lastly, it’s about the lessons. So, we look at the deals we lost in the last 7 days:

  • Why did they go to close-lost?
  • What could we have done differently?
  • Is there any feedback for Marketing, Sales, or Product that helps us win this deal next time?

Create opportunities for virtual social activities

Remote selling adds more weight to the saying “selling is more than selling.”  

In the wake of “the Great Resignation,” it’s important to provide mentorship and support for your sales team. The lack of in-office interactions and working across time zones mean you must be proactive about team bonding. 

For every win, we schedule a five-minute call with everyone and we celebrate the deal and the rep. We also have virtual team lunches (food on UserGems) every Thursday afternoon.

Graphic with text Encourage virtual coffee chats

Invest in remote sales enablement tools

If you want your sales team to do their best work, empower them with remote sales enablement tools for every stage of the sales cycle. 

Sales enablement tools help unify your marketing and sales teams, enabling the sales team to have readily available content that can move the needle on deals. It also keeps the marketing team aware of what content to prepare to help sales close deals faster.

Here are some sales enablement tools to consider

  • A cloud-based CRM: This ensures the marketing and sales team has an overview of pipeline activities and can collaborate on improving the buying experience for customers and prospects.
  • Create sales-enablement content: Ensure your sales team has access to marketing materials to help them close deals faster, like case studies, demos, and product guides. 
  • Automate prospecting: Prospecting is a labor-intensive task, and frankly, not all great salespeople are great at it. Use a B2B prospecting tool like UserGems to help your sales team prospect faster, identify those most likely to buy from you, and track sales trigger events. That way your sales team can focus on what they are great at — selling.

Managing a remote sales team is doable

If you’re hesitant to manage a remote sales team, remember that it’s an opportunity to put together a diverse lineup and tap into the best global talent. 

Make sure your sales motion is built for virtual selling, communicate your expectations to your team, equip them with remote sales enablement tools, and continuously examine areas where your team can improve.

Why UserGems

UserGems helps companies and remote sales team managers generate more revenue by combining relationship data with trigger events to surface the most relevant buyers for each company. With UserGems, customers get a bigger pipeline and win more often.


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