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How to Solve the Challenges of Managing a Remote B2B Sales Team

Managing a Remote B2B Sales Team
Last year’s
Global Leadership Summit predicted that more than half of all employees will work remotely by 2020. For companies used to having a centralized sales force, the move to a remote structure and organizational design has presented sales leaders and their front-line managers unique challenges. Here, we discuss the key challenges of managing a remote sales team and provide actionable solutions to overcome them.

Research has shown that employees and business leaders adapt differently to remote work. Because of this difference in perspective, challenges inevitably arise. As a sales leader, your ability to manage and solve the problems of a remote team can be the difference between a cohesive team that consistently makes their numbers, and one that is isolated and disjointed.

This article breaks down the most common challenges that emerge when managing a remote sales team – and provides solutions on how to solve them.

Challenge: Lack of Face-to-Face Communication

When you have a remote team, the critical processes of trust and rapport building can be weakened or not developed at all.  Because the primary mode of communication in a remote sales team isn’t face to face, you need to plan ahead to develop trust and rapport. Ideally, this will happen early in the relationship with your sales team – whether or not you’ve inherited a remote sales team, or are in the process of building one.

Solution 1: Make distance a chance to prove you trust your team

Forum’s recent Global Leadership Pulse survey revealed that trust has a direct impact on the engagement levels of remote teams. Great sales managers turn the autonomy that flexible, remote work has to offer into a chance to show your team you trust them with certain responsibilities and tasks. This leaves your sales reps feeling empowered, engaged and connected – despite the distance.

Solution 2: Learn how to read between the lines

Great remote sales leaders need to be highly perceptive and attuned to the emotional cues you receive from your remote reps. This means you need to learn how to spot potential or existing problems from a distance.

Rely on effective questioning techniques, such as:

  • Open ended questions (require elaboration and cannot be answered yes or no)
  • Funnel questions (begin general and ask for more specific detail with each answer)
  • Probing questions (asking for examples, asking why, asking for clarification)

You will also need to rely on active listening skills, and look for any change in pitch, tone, or pace of exchange in your conversations to identify possible issues. 


Challenge: Employee Isolation

Research from the Journal of Personal Selling & Sales Management explains that workplace isolation is one of the most critical issues facing remote employees. The results of the study suggest that perceptions of workplace isolation negatively effect trust in supervisors and coworkers for employees.

Solution 1: Make check-ins informal

A practical way to make remote salespeople feel engaged with you as their manager is to eliminate the formality of weekly or daily updates and reviews. Rely on video and teleconferencing, or even text messaging to communicate with your team. The more frequent and less formal, the better.

While it’s still important to schedule formal one on one meetings to review results, pipeline, and activity if necessary, having frequent, less formal check ins in addition to formal meetings is a key way to prevent employee isolation.

Solution 2: Focus more on each individual  

With remote employees, trust replaces the traditional structures of hierarchy and control in a physical workplace setting. Build trust with your team, and facilitate trust building between your team members. To do this, you need to connect more on an individual level with each member of your team. Find a commonality or shared interest.

You can’t always talk about work with remote team. Spend some time focusing on the individual to keep them feeling connected and engaged.

Solution 3: Prioritize in-person interactions

The most successful managers of remote sales teams report that face-to-face forums, conferences, workshops and get-togethers are planned well in advance, and happen regularly. Such in person meetings provide opportunities for remote employees to interact professionally and socially with the people they work with. This creates a foundation in the team dynamic that facilitates trust and team rapport.              

You can start with an annual meeting at the headquarters of your company, and have the meeting structured well in advance. Use the time to provide in-person coaching and guidance, and allot enough time for socializing and developing personal rapport.

You are the best judge for how often your team needs to be together in person. If you want to meet more frequently, choose a sales conference to attend together. Plan this into your budget so it’s feasible for your team to attend.


Challenge: Sustaining Employee Engagement

In the same study conducted by the Journal of Personal Selling and Sales Management, organizational commitment and employee engagement is shown to be positively correlated to salesperson job performance. Measuring employee engagement can be a challenge with remote employees. This is because you lack the face-to-face interaction that traditionally allows managers to assess employee commitment to their roles and the organization. According to a report by Gallup, there are three ways to accelerate employee engagement:

Employees who are engaged in their jobs are generally in better health and have healthier habits than employees who are not engaged or are actively disengaged.

-Gallup Report on Employee Engagement

Solution 1: Select the right people

The first line of defense in keeping remote employees engaged is to prevent the problem from arising in the first place. 

As much as possible, ensure you are hiring individuals who are enterprising, driven, and able to work independently. While any sales role will require these characteristics to a degree, the amount of independent work required by a remote employee makes possessing these traits significantly more important.

Solution 2: Develop Employee Strengths

HBR reports that developing employee strengths is far more effective to boosting both sales and overall job performance than trying to improve weaknesses. Have your team take the Clifton StrengthsFinder assessment, and develop the strengths of your team based on their results. When your sales reps feel empowered, confident in their ability to perform, and supported in their roles, their engagement levels will remain buoyant, even as they face adversity.


Solution 3: Elevate Employee Well-Being

Gallup research found that when an organization increases employee engagement and well-being, it pays off in terms of lowering medical costs and accelerating important performance outcomes.


As a sales leader, you need to be highly proactive when managing engagement levels of remote reps. Work with HR to improve employee engagement that is specific to a remote work environment. One way to do this is to actually ask your remote employees what would increase their sense of well-being. This emphasizes your proactive leadership style and you learn what well-being means to your team.


Challenge: Employees Feel Invisible

The best sales leaders recognize that they are working with an array of personality types. Salespeople who have high needs for recognition may struggle more as remote workers. This is because they may feel they have to do more work to get recognized compared to in-office reps. For reps with high needs for recognition, a lack of acknowledgement can make them feel invisible.

Solution 1: Be vocal about individual and team contributions

As a remote manager, actively and consistently vocalize team wins and individual performances during team meetings and teleconferencing. This is a crucial way to make remote reps feel seen by their team and recognized by leadership.

Take the time to mention when team members upsell an existing account, close a sale, or hit their quarterly targets. For reps who thrive off recognition, these simple acknowledgements lead to higher rates of employee engagement, which leads to higher job productivity and performance, according to this research.

Solution 2: Advertise your accessibility

Make it clear to your team via a shared calendar or team project management board when you are available. This sets clear guidelines for how and when you will respond to phone calls, e-mails, or texts. Suzanne La Forgia, VP of Ad Sales for Captivate, explains that when you are managing a remote team, having reps who feel like they can reach out to you in any given circumstance is crucial for leading a top producing team.

“Across time zones, you can’t operate in a 9-5”

-Suzanne La Forgia, VP Ad Sales, Captivate

Solution 3: Be a supportive leader

Remote managers need to do better than traditional managers at demonstrating supportive leadership. This is because how leaders handle remote employees has been shown to be a good predictor of employee job satisfaction, commitment level, performance, and turnover intentions.

Supportive leadership is more crucial in remote teams because so much more of your team functionality and performance relies on trust. To make your numbers with a remote team, demonstrate high levels of support in your leadership style. This goes beyond weekly check-ins, and includes encouraging your team to take risks in developing new selling approaches, allowing for failure in new prospecting or selling techniques, or supporting them in personal goals they have outside of work.

Solution 4: Create a community where your team can interact

Integrate a technology that addresses the unique challenges of remote work. Creating a communal online space for your team to gather may help eliminate the anxieties remote reps feel due to a lack of visibility. It can include:

  • Information on each employee that includes personal information like hobbies, favorite activities, personal goals, etc.
  • Areas of expertise of each employee
  • Common interest area: recipes, fitness plans, playlists, photo sharing, etc.
  • A section for frequently asked questions that addresses the issues related to remote work and how these issues can be resolved
  • An informal chat space (i.e. virtual water cooler)


Remote Management Means Being a Proactive Leader

Managing your remote salesforce is not unlike managing an in-office team, but requires a heavier emphasis on trust building, creative and frequent communication, implementing team processes, and using technology to connect. As the manager of a remote sales force, be proactive and supportive in your leadership to get the best engagement and performance out of your remote reps.

Want more? Visit the Peak Sales Blog for everything you want to know about building a top performing sales team, from How to Close Your Top Sales Candidate, to conducting Faster, Better, Sales Onboarding.


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Eliot Burdett

CEO at Peak Sales Recruiting

Before Peak, Eliot spent more than 20 years building and leading companies, where he took the lead in recruiting and managing high performance sales teams. He co-founded Ventrada Systems (mobile applications) and GlobalX (e-commerce software). He was also Vice President of Sales for PointShot Wireless. Eliot received his B. Comm. from Carleton University and has been honored as a Top 40 Under 40 Award winner. He co-authored Sales Recruiting 2.0, How to Find Top Performing Sales People, Fast and provides regular insights on sales team management and hiring on the Peak Sales Recruiting Blog.