Mastering Virtual Sales Leadership: Insights and Advice from Top Remote Sales Managers

The COVID-19 pandemic didn‘t just disrupt business as usual – it completely transformed the world of work. Virtually overnight, remote work went from a nice-to-have perk to an absolute necessity. And few teams were impacted as profoundly as sales.

According to McKinsey, more than 90% of B2B sales teams shifted to a virtual sales model in the wake of COVID-19. Sellers accustomed to closing deals with a smile and a handshake suddenly found themselves navigating the complex world of Zoom calls and digital sales rooms. Leaders had to quickly learn how to hire, onboard, coach, and motivate dispersed sales teams – without any of the in-person interaction they were used to.

Now, as we enter 2024, one thing is clear: Virtual and hybrid sales teams are here to stay. A recent Gartner survey found that 51% of sales leaders expect the majority of their salespeople to work remotely at least part-time going forward. The question is no longer "when will things go back to normal?" but rather "how can we adapt and thrive in this new normal?"

The key lies in effective virtual sales leadership. In this new era of work, the most successful sales organizations will be those with leaders who can seamlessly connect with, motivate, and drive results from their remote teams.

But what does great virtual sales leadership actually look like in practice? What skills and approaches do the top remote sales managers employ to get the best from their teams? And how can leaders excel in an increasingly virtual future?

To find out, we spoke with three experienced sales leaders who have cracked the code on virtual team management. Here, they share their hard-won insights and advice on how to master the art of virtual sales leadership.

Understanding the Virtual Sales Leadership Imperative

Before diving into virtual leadership strategies and tactics, it‘s important to understand the stakes. Put simply, virtual sales leadership isn‘t just a nice skill to have – it‘s a critical business necessity.

Consider these statistics:

• 80% of B2B sales interactions between suppliers and buyers will occur in digital channels by 2025 (Gartner)
• 60% of B2B buyers say they hope not to interact with sales reps in person even in their post-pandemic "new normal" (McKinsey)
• 64% of sales teams that transitioned to remote work in 2020 met or exceeded their targets, compared to 50% of non-virtual teams (ringDNA)

The data paints a clear picture: Virtual selling is the future and sales organizations that can adapt and perform in a remote or hybrid model have a distinct competitive edge.

But there‘s a catch. That same ringDNA research found that sellers on virtual teams with effective leadership were 41% more likely to be highly engaged than their peers with ineffective virtual managers. In other words, virtual sales success starts at the top.

"There‘s no question that virtual is the default for sales teams now," says Damon Jones, Head of Global Strategy and Growth at Sandler. "The organizations that will win in this new world are the ones with sales leaders who can guide their teams to peak performance from anywhere."

What Great Virtual Sales Leadership Looks Like

So what separates great virtual sales leaders from the rest? According to the managers we spoke to, it comes down to four key things: connection, communication, trust, and coaching.

1. They prioritize human connection.

One of the biggest challenges of leading remotely is the lack of face-to-face interaction. When you‘re not physically together, it‘s much harder to build rapport, pick up on non-verbal cues, and create a sense of camaraderie.

Top virtual sales leaders understand this and go out of their way to create moments of genuine human connection – even from behind a screen. They keep their cameras on during meetings, encourage casual conversation, and look for ways to bond over shared interests.

Chris Gell, Sales Enablement Program Manager at Dialpad, makes it a point to start every team meeting with a fun, non-work related ice breaker. "We‘ll do things like ‘two truths and a lie‘ or ‘show and tell‘ with something in your workspace," he says. "It‘s a great way to learn about each other as people and build those personal relationships that are so key to team cohesion."

2. They communicate with intention.

Strong communication skills have always been essential for sales leaders, but they take on new importance in a virtual context. With fewer opportunities for organic conversation and information-sharing, remote leaders need to be purposeful and proactive in their communication.

The best virtual sales managers establish clear norms and expectations around communication channels, frequency, and style. They share important updates in multiple formats, provide regular recaps of key metrics and priorities, and create open forums for two-way dialogue.

Kelly Knutson, Head of eCommerce Sales at Chargebee, sends out a weekly email to her team with top-level updates, shout-outs, and reminders. "It‘s an easy way to keep everyone aligned without having to clog up calendars with extra meetings," she says. "I always end by reminding the team that my (virtual) door is always open if they need me."

3. They build trust through transparency.

Trust is the bedrock of any high-performing sales team. But fostering trust in a remote setting, where you can‘t just pop by someone‘s desk to check in or address concerns in the moment, requires an extra level of transparency and intentionality.

Leading remote sales teams with a high degree of trust make transparency a core part of their management approach. They‘re open and honest about challenges, proactive in sharing both positive and negative feedback, and consistently follow through on their commitments.

"Trust has to be earned, especially when you‘re asking a team to follow you in a virtual environment," says Jones. "One of the best ways to do that is by being completely transparent, even when it‘s uncomfortable. If you‘re hiding information or not being fully forthright, your team will pick up on that and it will erode trust."

4. They coach to the individual.

Coaching and developing salespeople looks different when you‘re not face-to-face. Managers can‘t just listen in on calls or join ride-alongs to observe and give feedback in the moment. Virtual coaching requires a more data-driven, personalized approach.

The most effective virtual sales coaches use analytics and AI tools to gain visibility into each seller‘s performance, identify skill gaps, and deliver targeted coaching. They tailor their coaching style to resonate with each individual and set aside dedicated time for focused development conversations.

"Coaching remotely is all about meeting sellers where they are," says Gell. "Some reps respond well to role play and practice, others prefer to review game tape, and others do best with self-guided exercises. As a virtual leader, you have to understand those individual preferences and adapt your approach."

Putting Virtual Sales Leadership Into Practice

Understanding the core tenets of great virtual sales leadership is one thing – actually putting them into practice is another. Here are some tactical tips and strategies shared by our featured leaders:

1. Schedule regular 1-1 meetings with each team member to check in on both work and life. Use the time to discuss challenges, provide coaching, and just catch up on a human level.

2. Create a "virtual sales playbook" that codifies key processes, best practices, and resources. Make it accessible to the entire team and update it regularly as new learnings emerge.

3. Utilize video as much as possible for meetings, coaching sessions, and casual check-ins. Seeing faces regularly helps build connection and makes communication clearer and more engaging.

4. Establish a regular meeting cadence that balances team alignment with individual focus time. For example, hold a weekly team standup, bi-weekly pipeline review, and monthly training session.

5. Publicly celebrate wins and recognize great work often. Use a team Slack channel or email thread to share success stories, shout out top performers, and keep motivation high.

6. Invest in learning and development. Provide access to virtual sales training, online courses, and professional development opportunities to help sellers continuously sharpen their skills.

7. Lead by example with things like keeping your camera on, showing up on time for meetings, actively participating in team activities, and maintaining a positive attitude.

8. Encourage non-work related conversation and interaction. Create virtual spaces for "water cooler" chat and casual connection, like a team Slack channel or optional Friday morning coffee hour.

"At the end of the day, leading a virtual sales team is about being intentional," says Knutson. "You have to put in the extra effort to connect with people, to communicate clearly and often, to build and maintain trust, and to adjust your coaching approach. It‘s not always easy, but it‘s so worth it when you see your team thriving."

The Future of Virtual Sales Leadership

As we look ahead to the coming years, one thing is certain: Virtual and hybrid sales teams are the new normal. Gartner predicts that by 2025, 80% of B2B sales interactions between suppliers and buyers will occur in digital channels. And McKinsey research shows that more than three quarters of buyers and sellers now prefer digital self-serve and remote human engagement over face-to-face interactions – a sentiment that has steadily intensified even after lockdowns have ended.

What does this mean for sales leaders? It means that mastering the art of virtual team management isn‘t just a pandemic-era necessity – it‘s a critical skill for long-term success. The sales leaders who can effectively connect with, motivate, and drive performance from remote and hybrid teams will have a major advantage in the years to come.

But virtual sales leadership isn‘t just about doing the same things you did in person, only through a screen. It requires a fundamental shift in mindset, skill set, and approach. Leaders need to embrace new technologies, communication styles, and ways of building trust and alignment. They need to get comfortable coaching and developing talent in new, data-driven ways. And they need to continually experiment and iterate to find what works best for their unique teams.

The good news? The virtual environment also offers big opportunities. Sales organizations can widen their talent pools, offer employees unprecedented flexibility, reduce costs, and gain new levels of insight into customer engagement and rep performance. With the right virtual leadership strategies, the possibilities are endless.

"Virtual selling is an exciting frontier," says Jones. "Yes, it comes with challenges, but it also opens up a world of opportunity for sales teams willing to adapt and innovate. The key is having leaders who can see that opportunity and fearlessly lead their teams into the future."

Embracing the Virtual Sales Leadership Imperative

The shift to virtual and hybrid sales is no longer a question of "if," but rather of "how quickly and effectively can we adapt?" As the B2B sales cycle continues to digitize and buyers increasingly prefer remote and self-serve engagement, sales organizations simply won‘t be able to compete without strong virtual leadership.

Fortunately, as the insights and advice shared here demonstrate, the roadmap for virtual leadership success is getting clearer every day. By prioritizing connection, being intentional with communication, leading with transparency, coaching to the individual, and continually investing in new skills and technologies, sales leaders can unlock the full potential of their remote teams.

Embracing this virtual future won‘t be easy – it requires a significant mindset shift and a willingness to let go of old ways of working. But the alternative – stubbornly clinging to an in-person sales model in an increasingly virtual world – is a recipe for obsolescence.

The virtual sales leaders who will win in the years ahead will be those who see this moment not as a temporary disruption, but as an opportunity to reimagine how they connect with customers, develop talent, and drive revenue. They‘ll be the ones who aren‘t afraid to experiment, iterate, and fail forward in pursuit of a better, more flexible and resilient sales model. And they‘ll be the ones who recognize that in a virtual world, leadership isn‘t about command and control – it‘s about trust, transparency, and adaptability.

The future of sales is virtual. Is your leadership ready to embrace it?