10 Hidden Sales Enablement Challenges Blocking Your Team

Sales enablement is changing. 

Traditionally, sales enablement has focused on supporting salespeople in closing deals. Now, many programs are shifting focus to the buyer, ensuring they have the information, resources, and guidance to make informed decisions on their own. 

And sure, a large part of this is because teams are more distributed today, which makes it harder to onboard, ramp, and get visibility on reps. It doesn’t help either that budgets are getting increasingly scrutinized and teams can’t just keep buying more tools without justifying the spend.

But what buyers want has evolved too.

This shift has led to the rise of sales strategies that empower buyers to make informed decisions instead of just arming sellers with information. In other words, sales enablement teams aren’t serving just sellers anymore.

Let’s dive into some of the biggest challenges facing sales enablement teams right now—with tips along the way from Lish Barber, Senior Director of Enablement at Sigma Computing, who spoke with us recently about all things sales enablement.

1. Buyers spend less time with sales

Modern buyers are more independent, more informed—and less willing to spend time with sales teams. The old ways of enabling sellers (heavy on training, content dumps, and process documentation) no longer align with the buyer’s journey. 

Today’s buyers spend less evaluation time meeting with potential suppliers, preferring instead to do their own research and educate themselves with content. 

According to G2, 74% of buyers expect content expertise from companies, and the same percentage will choose the company that first adds content value. 

Coupled with larger stakeholder teams and non-linear buyer journeys, it’s harder for sales teams to exert influence and move deals forward the way they used to:

Solution: Shift from sales to buyer enablement

Instead of focusing your sales enablement efforts on your sellers’ needs, look for ways to make things easier for your buyers. 

This is known as buyer enablement and involves creating content, tools, and systems that help your buyers through their decision-making process.

What does buyer enablement look like in practice?

1. Help the buyer reach their goals

• Map the buyer’s problems and goals to your solution
• Create a business case alongside your champions
• Help the buyer make the right decision for their business
• Be honest about product fit
• Build an implementation plan, not a sales close plan

2. Support the buyer’s research

• Create external collateral that helps the buyer collect information (like ROI studies, competitor side-by-sides, and product feature demos)
• Be upfront and transparent about pricing

3. Trying before buying

• Give pathways for buyers to see how the product will work for them (like POCs, free trials, demo recordings, or a demo sandbox)

To succeed, you need to make sure that every team member is equipped with tools that facilitate outreach and communication with all stakeholders in the buyer's journey. 

This doesn’t just mean shifting your content creation to focus on what prospects need—it’s also an opportunity to empower your sales team to enable buyers by giving sellers easily accessible resources.

Dock’s digital sales rooms, for example, are customizable interactive microsites that let revenue teams embed different types of content on the page, including pitch decks, pricing proposals, videos, mutual action plans, and task lists:

Having all this content is important for buyer enablement because it makes it easier for buyer champions to advocate for your solution to their stakeholders, and also helps your own team track multithreading as the buyer evaluates your product internally.

2. The perfectionism trap

Sales enablement teams sometimes fall into the trap of trying to build the “perfect” training program, which delays decision-making so much and creates so many bottlenecks that nothing ends up getting done.

Solution: Build the tugboat first

Perfect is the enemy of good enough, especially in fast-moving sales environments. “Something is better than nothing. Start little by little,” Barber recommends.

“Over time, that tugboat, if you can build the tugboat, it becomes the cruise ship and that world-class onboarding program.”

When Barber was building her enablement program, she started with the most important things new hires need to know in week one, then over time, they would look for topics that might be missing from a cohort and gradually refine that process. “It became a really awesome onboarding process just through constant iteration,” she says.

3. Cross-team collaboration and alignment

Even as the lines between sales, marketing, customer success, and revenue operations blur, it’s increasingly difficult to keep these teams aligned.

Misaligned teams create friction in the buyer experience, slow down deals, and lead to disjointed messaging. 

Sales teams, for example, tend to copy the same demo follow-up email every time and they often don't swap out the links or attachments for the latest and greatest content that the Marketing department is spending so much time and effort making.

For Barber, collaborative success is intrinsically tied to measurable business outcomes. “For me specifically, I know I'm doing my job well if revenue is going up and cost of sale is going down. I think if RevOps is the process maker and they're driving efficiencies, Enablement is doing the magic to drive effectiveness,” she says.

“Whether it's a problem that's being driven from sales leadership and needs PMM support, or Product is launching something that'll need sales enablement support, our roadmaps overlap.”

Solution: Align teams around revenue enablement

To nurture cross-team alignment, adopt a revenue enablement approach that aligns partners such as Marketing, Customer Success, and Product teams around shared goals, tools, and metrics.

What is revenue enablement? Revenue enablement is a relatively new concept that means providing revenue-generating teams (i.e., Sales, Marketing, and Customer Success) with the tools, resources, training, and knowledge they need to win deals and retain customers at every stage of the customer journey. 

But that’s not all. Revenue enablement also encompasses the buyers’ side—giving customers the education and tools they need to make an informed buying decision and be successful with your product.

Certain tools are designed to facilitate cross-functional collaboration by revenue teams as well. 

For example, Dock provides a single source of truth across the customer lifecycle and centralizes critical information for every team, which reduces the risk of siloed content and fragmented handoffs:

4. Acting proactively instead of reactively

A common challenge is ensuring your enablement efforts are proactive instead of reactive. 

Lish pointed out that many sales leaders only focus on enablement when there's an immediate problem rather than using it as a strategic tool to drive growth. This reactive approach limits the ability to build comprehensive and effective sales enablement initiatives​ over the long term.

Solution: Develop a strategic enablement framework with anticipatory goals

Establish a long-term enablement framework that’s aligned with business goals and potential market trends. 

You could do this on a quarterly or annual cycle, which would help sellers get ahead of upcoming product launches, changes in buyer behavior, or new competitive threats.

This is also where regular collaboration with cross-functional partners (like Product Marketing and Product) will be helpful, as they will bring a different perspective on gaps and opportunities.

5. Proving ROI to the buyer 

Today’s SaaS buyers are becoming increasingly risk-averse. They need a clear and compelling ROI story to justify their purchase decisions to internal stakeholders—particularly the finance team. 

What that means: The burden of proof is on your sales enablement team.

Solution: Have a strong ROI story for your economic buyer

Sales teams must be armed with data-driven, personalized ROI stories for each decision maker who will have a say in whether you’ll win the deal. 

But your economic buyer—the final decision maker and financial gatekeeper who decides whether or not to spend money on your product or service—is your most important target.

You can’t rely on just general case studies to make your case here. Instead, personalize an ROI story using content such as:

• ROI-focused case studies that highlight specific pain points and measurable outcomes that matter to your audience, such as industry-specific challenges, company size, or unique operational goals
• ROI reports (a good example from Gong here)
• ROI calculators (an example from Cognism)

With a platform like Dock, you could position this ROI content front and center for your economic buyer to help them make a business case. 

Here’s how that might look in a Dock deal room. Note the tailored sections dedicated to the business case, pricing details, and even implementation plan: 

Not only does this make it easy for prospects to interact with your sales and marketing materials, it also empowers your sellers to build credibility and trust with the economic buyer, and provide a more consistent buying experience.

6. Timing of Sales Enablement involvement

Barber stresses that companies often bring in a sales enablement team too late in their growth. 

Once you hit product-market fit, it’s critical to onboard Sales Enablement as soon as possible to help scale efficiently, as waiting too long often forces enablement teams to waste time playing catch-up instead of proactively laying vital groundwork​.

Solution: Integrate Enablement early to build a scalable foundation

Ideally, Sales Enablement should be brought in as soon as the company achieves product-market fit. 

When Enablement starts early, they can create a structured, repeatable onboarding process for new hires, build alignment on messaging and positioning, and ensure all sales reps have access to the same training and resources. 

This avoids the scramble of playing catch-up and supports alignment to revenue goals and more sustainable growth.

7. Training uptake and retention

Training sales teams is an ongoing challenge for sales enablement leaders, especially in a remote selling environment.

Remote sales environments make it even more difficult to onboard new hires, ramp them up, and gain insight into where they might be struggling. With products, features, and competitive landscapes always changing, this cycle of retraining only intensifies over time, which creates an ongoing strain on resources and efficiency.

And even once new reps are onboarded, the need to constantly retrain sales reps every time products or messaging are updated can be frustrating, time-consuming, and costly. 

Barber suggests a pitfall to avoid during sales training is over-relying on the LMS:

“I've talked to so many salespeople over the years, and not a lot of them love spending hours in an LMS, which doesn't surprise me.”

Solution: Don’t rely on your sellers’ memories 

Not every new hire comes to you with the same level of experience, knowledge, or skills. Sure, it would be nice if you could hyper-personalize your training for each person’s specific gaps, but that would be wildly inefficient. 

So, instead of banking on your sales team remembering every tiny detail about every persona or every competitor, make it ridiculously easy for them to find the right content when they need it.

“I use the LMS as a primer,” says Barber. “It shouldn't take more than eight minutes to go through something, and it should be used to prep them for live training—giving them a bit of context before they come to learn a brand-new motion, persona, or part of the product.” 

8. Content discoverability and usage

Even the best sales collateral is useless if your team can’t find it. The average seller spends hours digging through company wikis, Google Drive, your website, LMS, and more for relevant content when they should be focused on closing deals.

There’s also often a mix of internal and external content in sales enablement content repositories, which makes it confusing for reps to know what can be shared or not. 

For example, internal-only sales onboarding and comp plans often sit right next to customer-facing assets.

The result: Only a fraction of the content produced actually gets used.

Solution: Focus on easy organization, access, and sharing

There’s no shortage of CMS options for sales managers to choose from—but many of these are not organized intuitively and difficult to integrate into existing sales workflows, making it hard for sellers to find and use content effectively. 

Look for tools that make it easy for sellers to quickly access and share relevant materials with prospects. 

For example, Dock’s content management system is designed to make life easier for both the reps who are using the content and enablement team members who have to manage the content. 

Sellers are able to find content in as few clicks as possible with boards and tags, and because the content journey can be prebuilt in digital sales rooms, they don’t need to spend as much time manually searching for one-off assets. 

If a piece of content needs to be updated, the enablement team can quickly push a mass update to everywhere the asset appears simply by replacing the file. 

The result: Reps are set up for success, and the right content is always easily accessible and consistently used—at the right stages of the sales process.

And Dock’s pre-built deal room templates make sharing content with clients even simpler. Sellers can use deal rooms that already have all the right decks, proposals, and more in place without the need to hand-share each asset.

This lets Enablement really craft the perfect content journey for the customer.

9. Not knowing what resonates with buyers

On a related note, it can be hard for sales organizations to always know what content and tactics are moving the needle in the buyer’s journey. 

Often, teams try to establish a feedback loop (What content is Sales using? What content resonates with prospects?), but this can be a resource-intensive cross-functional project. 

Solution: Use content analytics to track buyer engagement 

Good sales enablement platforms or content management solutions should come with built-in analytics that provide clear visibility into what content is being used, how it’s being consumed by buyers, and what’s driving deals forward. 

This data is crucial for sales enablement teams to refine their content strategy and provide more effective resources that actually resonate with buyers.

Dock, for example, provides real-time analytics and insights to help enablement teams regularly adjust and enhance their content based on what resonates with prospects:

10. Proving and measuring internal ROI

Sales enablement teams are under pressure to do more with less while still proving they’re having a measurable impact on revenue. 

But this isn’t always easy to do—how can you quantitatively measure something as intangible and subjective as learning? Or reliably track how many prospects are engaging with enablement content?

Not only that, but sales enablement software also typically lacks these essential features for proving and measuring ROI. 

Many platforms don’t support content organization across multiple locations, provide only limited analytics, and have weak CRM integrations—if they exist at all. These gaps make it difficult for teams to track content performance effectively and demonstrate a clear, measurable impact on revenue.

Solution: Equip your team with the right tools for ROI tracking

Whether you’re looking at impact on sales cycle length, closed-won deals, or win rates, you need data to prove ROI. And to obtain that data, you need to have the right sales enablement tools.

While many content management systems don’t have strong built-in analytics, there are some nontraditional solutions that do. 

Dock, for example, integrates with CRMs like Salesforce and HubSpot to add Dock’s engagement data (including utilization rates on the sales reps’ side, and also buyer engagement rates on the customer-facing side) to lead scoring models, forecasting reports, and customer health scores.

When trying to measure ROI on the training side, Barber suggests that while you can use certifications to help ensure sales reps are passing muster, certifications alone aren’t enough. 

The more important metric is repeatable sales success. “It's all good to get certified internally, but you should also be able to do it and show us that you've done it again and again and again in Gong,” says Barber.

Ready to up-level your sales enablement strategy?

The sales landscape is evolving—fast—and to rise to the occasion, sales enablement leaders have to adopt a more buyer-centric, data-driven approach. 

Buyers are more independent, decision processes are more complex, and revenue teams need to collaborate more effectively to align with these changes. 

By focusing on buyer enablement, cross-team alignment, and leveraging data to prove value, sales enablement leaders can empower their teams to consistently perform at a high level. 

Learn more about how non-traditional sales enablement solutions like Dock can equip your sales team to overcome objections, book meetings, and close deals as efficiently as possible. 

Dock is free to try. Try it here.