The Challenges of Training Remote Sales Teams

Your piano teacher was right after all. Practice does, indeed, make perfect. Learning anything cold is about doing it over and over again yourself, instead of just reading about it.

At your company, for example, salespeople and other client-facing members of your team need to know the right thing to say each time they speak to someone.

Expertise in something with as many variables as a prospect conversation doesn’t come through rote memorization, but with thorough training on the conversational building blocks that allow employees to internalize the core concepts.

That’s why role-playing is considered a vital part of training customer-facing employees. Whether it’s a call center, a sales team or an onsite technician, these workers need to inherently understand successful approaches to the job on the fly. Using role-play exercises allows workers to learn quickly and practice to perfection.

Quite often, though, it’s precisely because these colleagues are customer-facing that they also work remotely. And effectively role-playing with remote employees is problematic.

Remote workers already miss out on much of the water cooler “tribal knowledge” – timely information about the company, customers, competitors, products and messaging. On the other hand, much of this knowledge spreads through the home office virally in short little stories.

Remote workers typically only get sparse echoes of these important stories because there isn’t a systematic way to share them with the field.

Why Remote Training is Difficult

The issues with role-playing in a remote training context are threefold.

(1) Carving out available time across time zones and customer-centric schedules.

Sales reps’ calendars in particular tend to be mere suggestions of what they might do, if nothing better comes up with a prospect. So getting sellers together to role-play in addition to the weekly sales meeting can be difficult, even if you are able to make the multiple timezones work.

(2) Timely delivery of training materials.

When a key sale or new product feature occurs, it’s difficult to distribute that information to remote workers or train them on the correct reactions in real time.

Delivery of a case study, for example, can take weeks or months to a remote workforce, while onsite employees may have picked up the nuggets around the water cooler as it happens.

(3) An ineffective training format.

Because the workers are remote, they’re being trained with case studies and written material that neither provides a strong coaching / feedback loop nor encourages them to practice what they’re learning.

Because supervisors and remote workers interact only sporadically, and most have no idea what the remote employees are saying “out there” on the company’s behalf, it’s difficult to provide feedback and re-train staff.

SOLUTION: Find the Right Training Tool

One solution is to employ a training tool that allows remote workers to view a video of experts telling the stories, role-play them when it fits their schedules and get coaching and feedback on an ongoing basis. The right app would also be a platform for disseminating training across distributed teams.


Skype and other video conference tools do some of this. Trainers can make and distribute video presentations this way. Remote teams can theoretically get on a video call, practice the material and give and receive feedback.

But these tools don’t put all the information needed to learn a story in one place (the expert video, the story summary in a ‘cheat sheet’ format, a practice area and links to background information), allow re-recording of role-plays, joint reviews of the videos, etc. These gaps are not surprising because these tools were not designed to be role-playing platforms.


This is where newer applications like SharperAx are rising to fill the gap. SharperAx allows supervisors to upload “master” videos for the training module, lets employees record their own videos – several versions can be saved simultaneously – on their own time, and then informs the manager when the video is ready for review.

As a result of this approach, a company can capture an expert telling a story and deliver it to the field where a salesperson can master it, all in less than an hour.

This is a vast improvement over the historical collection, distribution and training cycles, which could take weeks or months. And this solution includes video, which, for this type of learning, is superior to written material alone. All the employee needs to get trained is a laptop, web access and a webcam.

The idea is to make remote training something like batting practice.

Workers can review and practice when no one is watching, in the safety of their own space. When they have mastered the story, they share it and get feedback at a time convenient to their manager or trainer.

This way, when they get into the game – a conversation with a customer or prospect – they are thoroughly prepared.

The result will be customer service and sales teams that are more adept at dealing with their target clients, delivering better service, and closing deals faster than ever.

Related: Why Are You Losing your Sales Teams?

What Next?

If you need help with sales support, here are a few options to help you:

  1. Download our eBook “Spend More Time Selling with a Virtual Assistant” and get a better understanding of how a virtual assistant can handle tedious sales tasks to give sales leaders and teams more time to sell and take care of customers.
  2. Book a free consultation call with Quickskill. We can help you regain more of your time to sell by offloading repeatable tasks to a fully managed virtual assistant. One of our experts will help you create a plan to delegate your tasks and we will even train your sales assistant for you.
  3. If you know someone else who’d benefit from sales support, share this post with them via email, LinkedIn, Twitter, or Facebook.