Managing a sales team is tough, but doing it remotely? That’s a whole new challenge.
Recently, a sales manager told us, “It’s harder to keep a pulse on the team’s activities and morale when everyone’s remote.”
In another conversation, a second sales leader reiterated this by sharing, “We’re struggling to maintain the same level of collaboration and communication we had pre-pandemic. It’s impacting our sales velocity.”
Remote work has undeniably changed how sales leaders manage their teams. Without impromptu desk chats or quick huddles, staying connected and maintaining performance requires a more deliberate approach—and better tools.
With the right technology and approach, remote teams can be just as effective, if not more so, than their in-office counterparts. But how do you make that happen? That’s exactly what we’ll cover.
The Key Challenges of Managing a Remote Sales Team
In-person sales team management comes with its own challenges, but doing it virtually adds extra layers of complexity.
1. Communication and Collaboration Slows Down
One of the biggest hurdles is the loss of spontaneous, in-person collaboration.
In an office setting, a sales rep could just turn their chair around or walk over to your desk for a second opinion. For example, let’s say a rep is negotiating with a key prospect and unsure whether to offer a discount to close the deal. They might swing by your desk and ask for your input.
This kind of real-time interaction is less likely to happen in a remote setup. The rep might hesitate to send a message, not knowing how quickly you’ll reply if they’re sending an email to the prospect right then, or scheduling a formal meeting might feel like overkill for just this one question.
As a result, they may make a judgment call on their own—offering too much of a discount or none at all—without a second opinion. The wrong decision could jeopardize the deal, and it might be too late to correct course by the time you're looped in.
2. Lack of Visibility into Sales Activities
Another big complaint by sales leaders? "I can’t see what’s going on." Without physically hearing your reps on calls, it’s hard to know who’s working on what, how deals are progressing, and what needs your attention. Sure, you can quickly check your CRM to see what’s going on.
That said, relying on a CRM alone to track your reps’ performance has limits. Data points can lack nuance, making it difficult to truly gauge a rep’s engagement or where they may need your support.
So, ultimately, you’re left wondering: Are my reps just going through the motions, or are they genuinely motivated and feel supported?
3. Inconsistent Execution and Limited Coaching
Remote work can lead to reps straying from core sales processes, which makes it harder to spot when pipeline discipline or deal velocity slips. Without real-time visibility into rep performance, missed opportunities and deal-stalling behaviors can go unnoticed until it’s too late.
Coaching is also tougher in a virtual environment. The absence of hands-on training means reps risk misaligning on value propositions or losing focus on key selling points. As a result, keeping consistency across the team is another major challenge many sales leaders are grappling with.
So, how do you go about addressing these challenges? Well, there are a couple of things you can do!
How To Manage a Remote Sales Team Effectively
Managing a remote sales team comes down to three things: structure, communication, and tools.
With the right systems in place, you can overcome the hurdles of distance and ensure your team is as productive, engaged, and aligned as they would be in the office.
Here’s how:
1. Set Clear Expectations & Goals
Remote work leaves less room for ambiguity. You can’t just assume your team knows what’s expected—they need clarity on what success looks like from the start.
Set clear, measurable goals that define what winning means for your team.
For example, you might set goals like “each rep needs to schedule five new demos per week” or “$100K in closed deals by the end of the month.” Activity goals should align with long-term revenue targets, and both should be visible to the whole team through a shared dashboard.
2. Prioritize Communication and Collaboration
In a remote environment, over-communication is always better. It’s also always easier to adjust down than up.
Schedule regular check-ins, both one-on-one and as a team, to keep everyone aligned. For instance, a daily 15-minute huddle via Zoom can keep the team focused on priorities, while a weekly one-on-one can provide space for deeper coaching and feedback.
Use tools like Slack for quick updates or to help with any issues your virtual sales team has. To keep things running smoothly, you could create specific Slack channels for deal updates, team wins, and troubleshooting. You’ll need to show your team the behavior they should emulate by using Slack for the same type of questions and updates you want them to send so they feel comfortable using the medium.
3. Use Technology to Support Remote Selling
Tech is your best friend when managing a remote team. CRM systems like Salesforce or HubSpot provide real-time insights into who’s working on what and where deals stand.
Sales intelligence solutions like Momentum automate call summaries, track deal progress, and alert you to risks in real-time. Momentum integrates with tools like Slack, keeping your team up to date on pipeline status while automating repetitive tasks like Salesforce CRM updates. This not only gives you visibility into the deals but also frees your reps from admin work, allowing them to focus on selling.
Related: 8 Tools You Need in Your B2B Sales Tech Stack
4. Provide Ongoing Training and Coaching
Just because your team is remote doesn’t mean you should pause their development.
To ensure your team continues to grow and excel, prioritize continuous development through structured training programs.
One thing you can do is role-playing. While the typical organization requires sales reps to engage in two to three role-play scenarios annually, top-performing companies elevate their game by implementing around six role-play sessions each year. By conducting virtual role-play workshops, your reps can refine their pitches, analyze real sales calls, and receive immediate feedback.
Alternatively, you can leverage Momentum’s AI-driven coaching to streamline and enhance remote training for your sales team.
Momentum’s AI technology automatically captures insights from sales calls, delivering real-time summaries that you can use to coach your team more effectively. Instead of relying on manual call reviews or waiting for end-of-month meetings, you can identify coaching opportunities as they arise.
For example, AI Signals will flag issues like weak discovery calls or missed objection handling so you can jump in with guidance at the moment it matters most. You can also set up custom call frameworks in Slack based on top-performing conversations, ensuring your reps follow best practices every time.
Using Momentum you can scale your coaching efforts and provide consistent feedback to your remote team without any time-consuming manual processes.
5. Foster a Strong Remote Culture
Remote work can feel isolating, so it’s important to build a culture that keeps your team engaged and motivated. Regular team meetings, virtual happy hours, or even a Slack channel dedicated to non-work-related chat can help maintain camaraderie.
For instance, you might set up a “Wins of the Week” channel where reps share their successes, big or small, to keep the energy high.
You’ll need to show your team it’s important by being involved and championing their involvement. Some will naturally get excited about the opportunity to connect with the rest of their team, while others might be more hesitant. At first, some may need to be pulled into the non-work conversations with direct questions until it becomes part of the culture.
6. Prioritize Sales Enablement Strategy Tailored for Remote Teams
Lastly, equipping remote sales teams with the right tools and resources is critical to their success. That’s where a well-rounded sales enablement strategy comes into play.
Here are a few ways you can enhance your reps’ performance, according to Gartner:
- Promote Innovation Within Remote Teams: Encourage your remote sellers to experiment with new approaches when appropriate. Foster a culture where innovation is supported, but ensure there are clear guidelines and feedback loops in place to prevent unnecessary risks.
- Redefine Learning with Just-in-Time (JIT) Nudges: Remote teams often need information on the fly. Just-in-time learning provides sellers with timely, relevant insights to help them make better decisions during sales interactions. This real-time support is crucial for distributed teams who may not have immediate access to peers or managers.
- Create and Distribute Remote-Specific Sales Playbooks: Sales playbooks become even more essential in a remote setup, providing a roadmap for success. Tailor them to your remote team’s unique challenges by including objection-handling techniques, best practices for virtual selling, and clear step-by-step guides for each stage of the sales process.
FAQs About Managing Sales Teams Remotely
1. What tools should I use to stay connected with my remote sales team?
Stick with what works best for your workflow. For example, you can use Slack for quick communication, Zoom for meetings, and Momentum for visibility into sales activities and reps’ performance. Also, don’t forget to use your CRM to keep deals on track.
2. How often should I check in with my remote team?
A daily 15-minute stand-up helps keep things moving, and one-on-one check-ins weekly or biweekly are great for more personalized feedback. Keep it balanced—don’t overwhelm the team with too many meetings.
3. What’s the main difference between managing a sales team in the office and virtually?
The biggest difference is visibility and spontaneity. In the office, you can see what’s happening in real-time, make quick adjustments, and have spontaneous conversations. Remotely, you need systems in place for real-time insights and structured communication. It’s less about “managing by walking around” and more about deliberate check-ins, coaching, and relying on tech to stay informed.
The Bottom Line
Remote teams can succeed if you communicate well, set clear goals, and use the right tools.
Momentum can help you get real-time insights and coach your team better. Want to lead your remote sales team to success? Schedule a call with our team to get started.