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Top 9 Sales Enablement Challenges That Sales Professionals Face

Sales Enablement Challenges

In modern sales, we cannot deny the impact of sales enablement. Businesses that deploy sales enablement solutions experience improved sales performance and productivity.

However, organizations encounter specific challenges when leveraging sales enablement, as with any strategy. In this post, we will evaluate the ‘Top 9 Sales Enablement Challenges That Salesperson Face’ and outline possible solutions to overcome them.

1) Measuring ROI on Sales Enablement

One persistent sales enablement challenge is quantifying the tangible business impact of programs, content, and technologies. Because there are many factors driving sales results making it difficult to isolate the ROI of specific enablement investments.

Measuring the business impact of enablement programs can be even more difficult in longer sales cycles, which is the most common in B2B sales. With that said, tracking leading indicators is crucial to ROI measurement. It keeps stakeholders engaged for the long term as revenue impact takes time to materialize.

When there are no clear ROI proof points, people perceive enablement as a “nice-to-have” instead of an urgent growth driver.

However, if you’re looking to measure your sales enablement ROI, here is the simple approach:-

  • Identify the metrics you want to track: Include both the expenses/investments made into sales enablement programs and the expected outcomes of sales team performance, revenue gains, etc. Also, get alignment from executives, sales leaders, and finance on the metrics.
  • Collect detailed data:  Get data on your identified metrics on the investment and return sides. This allows you to quantify the impact of the sales enablement programs.
  • Analyze trends in the data: Look at the data patterns over time and how the metrics track against goals. See if you can identify causal relationships between investments in enablement and upliftment in sales performance.
  • Make adjustments based on findings: Use the data and analyze the trends. Determine what’s working well in the enablement programs and improve what needs adjusting for better ROI.
  • Report ROI results: Share analysis and conclusions on sales enablement ROI with stakeholders and executives. This maintains credibility and alignment on the value delivered by enablement.

Remember to get stakeholder alignment upfront, and later, you can report ROI results based on an agreed-upon alignment. Better data, analysis, and alignment will make Sales enablement ROI conclusions more credible.

2) Sales Need Organized Content

It is a fact that in today’s business landscape, that content is paramount. Businesses need a variety of content to drive their marketing and sales processes. They need content for blogs, social media posts, white papers, eBooks, and case studies. 

When leveraging sales enablement strategies, content from sales materials often holds the key to the proper interactions. In a midsize organization, there is plenty of content for marketing, sales, product, and other teams.

To manage such a massive library of content, and on top of that, as an organization, you need to keep creating new content and make it accessible. This is where we need to organize this content so that it reaches the right individuals when required.

Maintaining a centralized repository for all of your sales collateral, product information, and sales scripts can be a huge task for sales. Poor content organization and accessibility often result in time-wasting and inefficiencies.

Fortunately, Our Sales Enablement Platform, Featurewave, can come to the rescue. Our tool collects existing content from all your repositories and helps organizations manage, organize, and access their content effortlessly. This improves the overall efficiency of sales operations.

3) Ramping New Hires

Sales enablement plays a crucial role in onboarding new sales representatives. The biggest sales enablement challenge is to reduce the learning curve for new hires without compromising their sales productivity.

This is a standard problem in most organizations because much of the training given to sales reps is not retained. Sales Enablement can combat this problem by providing sales reps with contextual guidance. Allowing our tool to guide sales reps and find answers to their searches wherever they work. 

Reps with instant access to marketing and sales enablement content are more capable and motivated. They can now explore the sales collateral in depth as there is no need to search for content. This develops a culture of continuous learning, skill-building, and expertise development.

Utilizing Sales enablement content can empower sales managers with smoother sales onboarding. It also lets them focus on high-return sales initiatives like coaching and mentoring. This creates a “multiplier effect” that enhances the overall functioning of a sales organization

4) Marketing and Sales Can’t Work Unsynchronized

The alignment of marketing and sales is critical. It helps in avoiding missed opportunities and maximizing revenue. 

People consider marketing and sales as two different operations. Today, when buyers come to sales with detailed product knowledge and research, it tells us that marketing and sales need to align for most sales to happen. 

The first step of better alignment is communication. Proper communication can help sales leaders ensure consistent alignment of campaigns, pacing of rollouts, and messaging across different campaigns.

A sales enablement tool that provides good customer data and sales insights can be helpful for both. Also, today, not only marketing and sales are responsible for revenue. There are other teams as well whose insights can matter while selling. For example, a proper guide on product knowledge that keeps your sales reps updated with the regular product changes is bound to make your rep appear as a product expert during customer interactions.

That’s why Enablement should span across revenue teams to make cross-functional alignment between multiple teams efficient. Maintaining connectivity among them can be challenging. However, one potential solution is to establish tight feedback loops across sales, marketing, product, and customer success teams.

5) Reps Aren’t Selling to New Pain Points

Organizations face a prominent sales challenge: sales reps often fail to adjust their selling strategy. They should address new pain points that prospects and customers reveal. Seasoned reps may rely too much on their tried-and-true sales pitches that worked in the past but no longer resonate in the same way with modern buyers.

That’s why sales and marketing teams must know new customer pain points. Otherwise, they’ll miss sales opportunities.

Making your reps well-informed about new pain points requires more immersive research. It also requires tighter marketing and sales alignment. Plus, it needs agile content development fueled by the latest customer feedback.

Here, the game comes down to having the updated sales content available for your sales team to pitch to customers with different pain points. 

However, using the right Sales Enablement tools like Featurewave. You can update and centralize your content. This will allow sales reps to stay informed about significant changes in marketing and sales. It will enable them to cater better to customers’ needs.

The best part is that our tool completes any content change in real-time, within minutes, thus resolving this sales enablement challenge.

6) Data Analysis of The Processes

Sales leaders can improve enablement by analyzing selling processes using data. This is one of the most impactful ways, and today’s cutting-edge analytic tools can give us unprecedented data into each step of the buyer journey.

Data from the sales enablement team are powerhouses of valuable insights, and proper analysis of this data can provide clarity on sales performance, customer behaviour, and market trends. It can also aid in strategic decision-making.

Not only that, you can diagnose the data to understand why your sales reps are not converting leads well. You can look into the people, content, messaging, competition, and other factors affecting conversion at each lagging stage.

For most sales enablement professionals, managers, and leaders to get access to the correct data, they need to leverage the right tools. Using data, if they find gap any in their training and coaching, they can quickly update their sales processes in the right way

7) Technology Integration

Today, sales enablement involves many tools. These tools include Customer relationship management (CRM) systems, Sales analytics platforms, Content management systems, and more.

Integration and utilization of these solutions can be complex and time-consuming. However, current sales enablement tools have robust integration capabilities. They can make the task seamless, reducing the effort of context switching for sales reps. 

The key here is the seamless integration of tools. Once the tools integrations are done, they should also help sales maintain the natural flow of tasks and processes. This includes online research, outreach, and deal closure. 

For example, You can integrate our Featurewave tool with Salesforce CRM within minutes, and it helps your sales reps become less dependent on your team or anyone else. Not to mention, it can guide reps across platforms, improving their efficiency.

8) Adoption and Resistance

There is this common sales enablement challenge, which is the resistance to adopt new initiatives, tools, and strategies across the sales teams. Enablement programs may be vital, but most sales reps can resist or be reluctant to change established habits.

Resistance to change is human nature. If your sales team is too comfortable with their previous scripts and processes when forced to learn new methodologies, tools, or talking points, there’s always an adopting period. It’s filled with uncertainty and lower productivity. 

To make this adoption of sales enablement smooth, organizations should emphasize the benefits of it. They should educate their teams on the positive impact these tools can bring. Regular training sessions can be an excellent start for that

9) Challenges in Prospecting

Prospecting relies on knowing your ideal client. Wasted effort in the wrong direction can impact your bottom line. For instance, even a top-performing account manager might struggle to deliver results if they don’t prospect.

Even though prospecting isn’t the fundamental sales enablement function, however, many teams struggle with prospecting. Reps do most of their prospecting, and if they lack an organized method for penetrating target accounts, researching key contacts, customizing outreach, securing meetings, and nurturing engagement over time. This cannot lead to effective sales even if the formal enablement is done right.

However, Sales enablement tools can provide beneficial insights these days. This can help to craft a better Ideal Client Profile (ICP). Consistent coaching reps on these insights will improve prospecting.


Sales enablement can be a game-changer for organizations. But without a transparent process established by leadership, these initiatives can fall flat. To assist the leaders and the whole sales teams better, there is a need for the best of the best sales enablement software in place. This is because software drives collaboration, automated workflows, and delivers data insights.

The right Sales enablement software for your sales organization can solve obstacles, mitigate risks, and pave the way for a successful sales strategy. 

If you’re interested, you can check our Sales Enablement software, Featurewave, which is bound to help your sales reps win more deals and close deals faster with our AI-driven, just-in-time guidance.

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