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How to Overcome 5 Common Sales Enablement Pain Points

Sales enablement equips your sales team with the tools, training, and resources they need to close more deals, directly impacting your bottom line. It’s no wonder that over 77 percent of organizations with 500 people or more have a dedicated sales enablement process. But having a program doesn’t guarantee success. The ability to overcome common sales enablement challenges can help you create a solid and successful sales team and program.

Here are the most common pain points and strategies to push past to perform consistently.

Sales content is disorganized

Sales reps need to find essential information quickly and easily; even with intentional sales enablement, that’s not always a reality. 

An organization’s sales materials are often scattered throughout websites, brochures, Q&A pages, and more. You might have a treasure trove of information that answers key customer questions, but the sales reps don’t know where to direct prospects to find this information.

Take a moment to think about these questions:

  • Where is your buyer persona information stored?
  • What can sales reps access to answer common customer questions?
  • Where are product specs located?
  • What materials do you have for customer education, and where is it?
  • Where are your one-pagers?
  • Where can your sales reps and customers find case studies and testimonials?

As you go through this list, you’ll quickly notice if your sales and marketing materials are too spread out or disorganized. Having a centralized training platform like a learning management system (LMS) can help you keep everything in one place and make it searchable, saving significant time and frustration for reps and enablement team members.

Sales reps aren’t selling to customer pain points

A pain point is a specific problem that a customer is facing. Do your sales reps speak directly to a customer’s personal pain points when going through the sales process? 

If not, it could be because they aren’t clear on what those pain points are. It’s essential for sales enablement professionals to identify problems customers may have and then train your sales reps on how to address them.

To learn more about your audience’s key struggles, take a look at testimonials and reviews. You can see what your customers are saying. But pay attention to your competitors’ customers as well, you might find gaps in your approach.

Also, listen to the language customers use when describing their problems. You want to use that same language in your marketing materials and sales conversations. Finally, conduct surveys of your target audience. Find out what’s keeping them up at night and then make sure every sales call addresses solving that need. 

Having the right sales enablement tools allows your reps to understand the competitive environment quickly and focus their conversations on areas that customers care about most.

Marketing and sales teams aren’t working together 

Despite the fact that the marketing team and sales reps have the same goal—to acquire more customers—their efforts and messaging may not always be consistent.

Unfortunately, this gap can affect the customer experience. For example, customers may be getting information from marketing that doesn’t align with the conversations they have with sales reps. Or, marketing materials might be pushed to the marketplace before sales reps have appropriate training on the updated messaging.
It’s important to make sure all teams are aligned on your brand’s messaging and positioning. You want to ensure your sales reps and other team members are telling a consistent story and that all employees are speaking about your product or service in the same way.

“Your messaging creates memories. If we are going to create memories for customers, we don’t want to create conflicting memories. You want to make sure that all your teams march to the same drum beat. Otherwise, it’s going to feel disjointed. When something feels disjointed to a prospect, they’re not going to feel connected to you. Marketing and sales have to be marching arm in arm so that the sounds that your prospects are hearing are pleasant. Without that, your messaging can get drowned out.”


-Melissa Regan, Senior Sales Enablement Manager, WorkRamp

One way to do this is to create internal team training materials to ensure everyone is on the same page about your messaging and positioning. These training materials should include elements such as:

  • Messaging framework
  • Customer profile
  • Buyer personas
  • Competitive overview
  • Positioning statements
  • Audience messaging
  • Customer pain points

To roll out this training, consider using a system that allows internal teams to work together in the same sales enablement software. Also, set up frequent interaction between departments. If there are concerns, make sure that team members have someone they can talk to that can resolve the issue. 

New hires flounder after training

One of the most critical elements in employee retention is the onboarding process. Good onboarding increases retention by 82 percent. You want to set new employees up for success right away. 

Organizations may be pressured to move new hires to full independence too quickly, which impacts how much a new sales rep is able to learn and retain. Fortunately, with some tweaks, you can improve the effectiveness of your ramping process.

Make sure your onboarding process is focused on skills and expertise, not simply HR paperwork. Allow new hires access to all of the company’s marketing materials immediately so they can start exploring and understanding the benefits of your products and services. Finally, include one-on-one coaching time so that your team can address any concerns or questions individually.

“Ideally, the onboarding plan should be built to get sales reps ready to be on the phone by certain mile-markers,” according to Stephanie Middaugh, Director of Enablement at WorkRamp. “If an onboarding plan isn’t taking into account certain goals, it should be reworked. For example, ‘our current time to first deal won is 70 days, our goal is to get that down to 60 days.’ What needs to happen from a training and preparation standpoint to get them to that point?”

The best sales reps are self-starters, but they do need to be given the opportunity and time to learn your business. When people have the tools they need, thanks to a strong training program and ongoing access to marketing materials, they’ll continue to improve over time.

A one-size-fits-all mindset

There’s a common thought process among successful sales reps and management alike. Every successful individual tends to think that everyone should approach the sales process exactly as they do in order to get great results.

The one-size-fits-all mindset is far from the truth. Selling approaches are as unique as each individual buyer, and what works for one person may not work for another. The sales approach that works best for each rep depends on their personal strengths, the buyer, and the situation.

As a sales enablement team, you may need to overcome this idea. Perhaps you’re too focused on using sales enablement software in one way, or you have one training track for onboarding and ongoing training.

Or, you might face a management team that thinks their personal “best practices” need to be followed for every sale. If you don’t know how to face this challenge, your sales enablement team might be completely derailed.

The best way to overcome this challenge is to educate both your sales team and your leadership about the fluid nature of sales and how it has to adapt to different buyer situations. Train your sales team to adapt their approach based on the customer and situation.

By being flexible, your reps will be able to close far more sales.

Overcoming sales enablement challenges

If you face any of these sales enablement challenges, you’re not alone. Fortunately, the solution to many of these problems is to adopt a learning system that allows you to integrate your teams, offer ongoing training, and empower your reps to develop a flexible sales approach.

When you use a learning management platform like WorkRamp, you can not only close more deals, but you can also integrate sales and marketing more effectively, organize your resources, and improve employee retention.

Want to learn more about how you can use WorkRamp for sales training? Contact us to schedule a free demo.

Complete the form for a custom demo.

Anna Spooner

WorkRamp Contributor

Anna Spooner is a digital strategist and marketer with over 11 years of experience. She writes content for various industries, including SaaS, medical and personal insurance, healthcare, education, marketing, and business. She enjoys the process of putting words around a company’s vision and is an expert at making complex ideas approachable and encouraging an audience to take action. 

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