Graphic with screenshots from a video meeting
Graphic with screenshots from a video meeting

Managing a remote sales team for the first time? Feeling out of depth and unsure how to begin? 

You’re not alone. 

In fact, this is something we know a lot about as a remote-first sales team. 

Even if you are still firmly team in-office, 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 caused some companies to flounder.

In this post, we share:

  • Some of the most common challenges of managing a remote sales team 
  • A behind-the-scenes look at how we built and grew our own remote-first sales team 
  • The most important lessons we’ve learned along the way 

4 challenges of managing a remote sales team

challenges of managing a remote sales team

While remote sales teams have an opportunity to hire the best talent from anywhere in the world, it’s meaningless if they don’t make management and retention a priority. That means getting a handle on some of the top challenges that remote sales teams — including ours — face. 

1. Poor communication

From reps doing duplicate work to deals being dropped and unclear KPIs, these are all signs that your communication practices need an upgrade.

In-office reps can pop into someone’s office to get an update or clarify an issue. You can’t do that remotely. Instead, you need to strive to over-communicate. This helps to avoid confusion, build better relationships, and keep everyone on the same page. 

There are two things you can do when managing a remote sales team to get better at over-communicating:

  • Build a transparent team culture: Transparency builds trust and respect. When people on your team feel trusted and safe, they are more likely to be open and collaborative. 
  • Hire salespeople who are great communicators and who have worked remotely before: When you bake this into your hiring process, it means it’s easier to cultivate a collaborative sales team where everyone knows how to communicate clearly, be it through Slack, your CRM, or Zoom.

2. Lack of sales systems and processes

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. In reality, this means having a clear sales playbook, scripts/templates, SOPs, and regular 1:1 and group training. 

3. Working in isolation

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.

The pressure of the job plus the lack of in-person meetings is often detrimental to the mental health and well-being of both first-time and experienced remote sales reps. This leads to underperformance and burnout.  

Combat isolation in your remote sales team by:

  • Having regular 1:1s: As a sales manager, you should be meeting with each of your direct reports at least every other week. Instead of running through tasks and doing business as usual, it‘s better to encourage each rep to set the agenda each week. This gives you a chance to check in with them as people, not just employees.
  • Getting buy-in from your reps on KPIs: The best way to burn out your sales reps is by limiting their autonomy over the sales process or giving them unrealistic quotas. Avoid this by having them work with you to set their KPIs each month or quarter. Then, you use your 1:1s with them to check in and offer coaching.
  • Encouraging collaboration and small talk: While team-building activities will look very different depending on your company culture, nobody likes to work completely alone 100% of the time. This is why you should encourage your sales team to regularly chat with one another and with others in your company using non-work Slack channels, a weekly Zoom happy hour, regular in-person retreats, or something else. 

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. While you should always be looking to learn from what works for other remote teams, it’s just as important to experiment with new strategies and processes.

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

We’ve got you.‍

How to effectively manage a remote sales team

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.

remote selling best practices that have worked for us

1. 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. 

This means hiring not only for skillset but also intangibles, like communication skills and attitude.

In fact, if you're a sales manager building your remote sales team for the first time, look for generalists who are great communicators rather than specialists until you have a firmer grasp of what you need. 

For example, our first sales hires were account executives (AEs). But we made a point of looking for AEs who were skilled at both hunting and closing. 

“To give you an idea, an Account Executive is focused on being the closer, and the 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,” says Christian. “I look out for someone who thinks, ‘Yes, I have an SDR helping me, but I'm able to take my destiny in 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.

Christian Kletzl, CEO, UserGems

2. 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

This means making sure your team has the right remote sales training and tools. For instance, making sure they get notified automatically when a prospect changes jobs, so they can reach out. 

This also means that sales should be fully aligned not only with their core team but also with the marketing team. This ensures that sales and marketing are working well together and moving towards the same goal. 

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

From 1:1s to sales team meetings, regular check-ins help you stay on top of the pulse of your remote sales team. They allow you to identify issues early, provide support, and connect with your team. 

The best part is that these processes can be standardized. 

Here’s how we conduct our sales check-ins and quota review meetings when managing our remote sales team’s efficiency 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 in the bottom of the funnel
  • Expected value to close this month and next month
  • Close rate
  • Number of activities (emails & calls)

In comparison, here’s what our qualitative review process looks like: 

  1. Focus on the bottom of the funnel first. Go through everything that’s in trial or negotiation and have our remote sales team focus on: 
  • Whether there are any deals in which they can be uniquely helpful
  • Where they can contact the decision-maker or someone else on the prospect’s team to drive the deal forward
  1. Next, we have a report for deals without stage movement in the last 30 days. This shows which accounts are most likely stuck and need to be discussed. The idea is to help the AE think through a deal from an outsider’s perspective by asking:
  • When’s the next meeting? When was the last meeting? What’s the next step?
  • How can I contact the decision-maker or someone else in the team to drive the deal forward?
  • If there is no clear next step, let’s go back to the basics. What’s the lead’s 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 our remote sales team focuses on:  

  • Whether there are any high-priority deals, regardless of their stage, and if there are any deals where executive support could help
  1. Lastly, it’s about the lessons. So, we look at the deals we lost in the last 7 days and consider:
  • 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?

4. Create opportunities for virtual team-building activities

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

Kenny Powell, Senior ADR, UserGems

For every win, we schedule a five-minute call with everyone, and we celebrate both the deal and the rep. We also have virtual team lunches (food on UserGems) every Thursday afternoon. Additional things you can do as a team include regular donut chats on Slack, Zoom show and tell sessions and quarterly or annual in-person retreats.

Here's Ryan Iacoviello, Senior Account Executive, UserGems, on the value of our virtual team-building activities:

"The radical candor of UG fuels me. There are no secrets, and our team-building activities ensure everyone is on the same page about where we are going and what we need to do to get there."

5. Invest in remote sales enablement tools

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

Sales enablement tools help align 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 teams close deals faster.

Some great sales enablement tools you could consider for remote sales team management include:

  • 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. For instance, you can use a CRM like HubSpot, Salesforce, or Pipedrive to ensure the sales team has full pipeline visibility and no deals are getting lost.
  • Prospecting Tools: Prospecting is a labor-intensive task, and frankly, not all great salespeople are good 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.
  • Scheduling software: Make the process easier for your SDRs and AEs to schedule sales calls and demos. For instance, use scheduling software like Calendly or SavvyCal.
  • Revenue intelligence tools: From analyzing your sales email outreach to call recordings, revenue intelligence tools provide insights to help your reps close more deals. For instance, you can use a tool like Gong to analyze and provide actionable insights on sales reps’ calls.

How UserGems helps you to manage your remote sales team

Managing a remote sales team is all about communicating your expectations to your team, continuously examining areas where your team can improve, and equipping them with remote sales enablement tools. 

UserGems helps remote sales team managers generate more revenue by combining relationship data with trigger events to surface the most relevant buyers for each company. So, you can get a bigger pipeline and win more often. Request a free demo today. 

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