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How to Upskill Your Sales Reps

Aug 02, 2022
5 min read

A study by McKinsey found that an overwhelming 87% of companies report they’re currently experiencing employee skills gaps or expect to in the next few years. Nowhere is this challenge more critical than in sales, the biggest revenue driver for most organizations.

Today, companies must emphasize the continuous improvement of sales rep skills in order to hit their targets and meet revenue goals. In other words, upskilling — teaching additional skills that expand the capabilities of sales employees — has become essential.

In the sections that follow, we’ll explore what sales upskilling looks like in practice as well as 5 key sales rep skills companies should be focusing on in 2022.

Quick Takeaways

  • Key components of sales upskilling include customized training, sales enablement, onboarding and ongoing professional development, and leadership by example.
  • Gartner reports that empathetic, situationally-driven sales approaches lead to higher buyer confidence and better buyer decision quality.
  • The sales process should be an actionable roadmap for sales reps to follow.
  • Storytelling makes sales pitches and presentations more compelling, and customer success stories are a great way to incorporate it.
  • It’s critical for organizations to optimize their tech stack by teaching sales reps to use it to its full capacity.

Why Is It Important to Upskill Sales Reps?

Businesses today experience continuous change — technology, buyer behaviors, sales best practices, and other external market factors all now evolve at a rapid pace. As such, sales reps whose skills remain static over time will eventually experience difficulty hitting their targets.

Upskilling is necessary in order to keep pace with changing business demands, leverage new technology tools, and continually align the sales process with the modern buyer journey.

Companies that want to maximize their sales talent know it isn’t enough to rely on employees to upskill on their own. Instead, they need to embed it into company culture and provide ample opportunities for upskilling on company time.

But what does this mean in practice? Key components to a strong upskilling approach include:

  • Customized training - Training should be hyper relevant to sales role and experience level. For example, a veteran sales manager needs different upskilling than a new junior sales rep.
  • Accessible sales enablement materials - Sales employees should never have to chase important information about the brand, sales process, or offerings. Instead, sales enablement materials should be readily available to foster natural knowledge build and consistency in sales messaging.
  • Ongoing professional development - Upskilling should be a continuous process, not a one-time or few-time experience for new employees.
  • Strong onboarding - That said, new employees need exceptional onboarding programs to get them up to speed and shrink the time it takes to reach their highest performance potential.
  • Leadership by example - Managers and other sales leaders should naturally practice what they preach.

While these core tenets have stood the test of time, what does change are the specific skills most important to sales success. Let’s take a closer look at the sales rep skill companies should be prioritizing right now.

5 Sales Rep Skills to Level Up in 2022


Perhaps the most notable evolution in B2B sales has been the significant shift in control from the sales organization to the buyer themselves. Armed with more options and information than ever before, B2B buyers now approach providers later in the buyer journey and with higher expectations for a personalized experience tailored to their needs. 

The key to meeting this new challenge — empathy. According to Gartner, leveraging empathy to take a situationally-driven (rather than standardized) approach to selling both increases buyer confidence and can improve buyer decision making quality by 11%. To upskill your employees in the use of empathy:

  • Train sales reps to adapt their approach according to common buying situations
  • Refine ideal customer profiles (ICPs) and buyer personas and make them accessible
  • Encourage detailed buyer research, thorough sales discovery, and active listening
  • Emphasize the importance of focusing on pain points before features/benefits

Sales Process Knowledge

The sales process is like a roadmap for sales success, but it’s meaningless unless it becomes actionable to sales reps. The more your reps know and adhere to your sales process, the more consistent and predictable your sales revenue will be.

To upskill employees on their knowledge and use of the sales process, make it an everyday part of how they operate. Define milestones at each stage and clear processes for marking them complete. Align the sales process with your CRM system and other software systems that your reps use to accomplish tasks and track progress. 

Provide detailed initial training around the sales process to new sales reps and reinforce it at subsequent training sessions for current sales employees. In other words: don’t make it something your sales employees can easily discard. When the sales process is integrated into sales operations, reps are held accountable for — and become better at — executing it.

Effective Buyer Research

Just as buyers prepare for the purchase process by researching potential providers, salespeople should research their buyers in order to provide an optimized experience. In this case, we’re talking about research on individual buyers as they first enter the sales pipeline as leads. Train sales reps to spend time learning about buyers by researching their industry, mission, history, customers, news and more.

Company websites are a great starting point for buyer research, as are industry news sources and market research platforms. You can outline best practices for buyer research within your own organization, keeping in mind the ultimate goal of sales reps entering buyer interactions with as much information and context as possible.


Storytelling is a key contributor to making sales pitches and presentations more compelling. It also inserts an emotional component that helps to build connection with potential buyers. Your sales reps should be skilled at sharing stories that emphasize the value of your offerings.

Using customer success stories is a great way to do this — they provide an avenue for you to demonstrate real-world value and share actual results. Humanize the stories as much as possible by including information about real people and testimonials from your customers themselves.

Technology Adoption

Last but not least, optimize your sales tech stack by training your sales employees on how to use it — and enforcing the need to actually do it. This could mean training new employees on existing technology tools, training current employees on new technology tools, or getting your laggard tech adopters up to speed as needed.

Don’t settle for using technology tools at their standard minimum, either. Look for opportunities to leverage new features and optimize their impact on your sales success. Provide ongoing training to introduce new ways to use tech tools and encourage your sales reps to look for even more on their own.

Optimizing your sales tech stack and upskilling employees accordingly can lead to higher levels of automation and efficiency, cost savings, and of course higher sales revenue in the form of more closed deals.

Over to You

At Xactly, we love salespeople. Our Intelligent Revenue Platform supports them with precise plans, better incentives, and data-informed insights to give them more confidence in their pipeline.

Learn more about our solutions or schedule your demo today to get started.

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Xactly News Team

The Xactly News Team reports on the latest product, events and market trends taking place within Xactly and throughout the revenue intelligence industry.