Top 10 sales enablement challenges and how to solve them

Sales enablement is supposed to make life easier for sales teams.

However, for many organizations, it becomes another source of friction. In the world of sales enablement news, we often hear about the struggles teams face in meeting their sales enablement targets. Training and onboarding is difficult when company knowledge is scattered across various siloed apps.

Content is hard to find. Messaging is all over the place. Sales RFP can take forever. Senior management shows resistance to change. And reps are spending more time managing tools than talking to buyers. In fact, sales reps spend only 28% of their week actively selling.

If all these problem statements sound familiar, you're not alone.

In this blog, we break down the 10 most common sales enablement challenges and how to solve them. We'll also explore how AI sales enablement is helping teams work smarter, faster, and more effectively.

Challenge #1: Reps can't find the right sales collateral when they need it most

Your team has pitch decks, battle cards, case studies, and email templates. But when a rep is prepping for a call or following up with a prospect, they're digging through folders, old emails, or random chat threads.

The result? Wasted time, inconsistent messaging, and missed opportunities.

This is a classic sales content management issue. Reps need fast access to the right resources, ideally, right inside their existing workflow.

The solution: Unified semantic search

Top-performing sales organizations are automating up to 50% of non-selling tasks, freeing up 20% more time for customer-facing activities. This automation has led to a 30% improvement in sales productivity.

Use AI-powered sales enablement tools like SiftHub with unified semantic search capabilities. These platforms allow reps to surface what they need instantly, based on context, not just file names. It's a game-changer for sales productivity and helps ensure buyers are getting the best, most relevant content every time. Implementing effective content repositories is one of the critical elements of sales enablement.

Challenge #2: Messaging inconsistencies erode trust

Sales is a team sport. But when everyone, from marketing to sales to presales, is using their own version of the pitch, things start to unravel fast.

Let's say your product team launches a new feature. Marketing writes a blog about it. Sales throws it into a deck. Solutions engineers use the information for a Request for Proposal purpose. But no one updates the boilerplate, and now your reps are pitching different benefits depending on who's in the room or on a Zoom call.

That inconsistency can confuse prospects and derail deals. 79% of customers expect consistent interactions, and yet 55% of customers say that it feels like they are separately communicating with different departments.

The solution: Automated Q&A management

Implement automated Q&A management. These tools ensure that everyone, across teams and roles, uses the same approved answers. With real-time suggestions, reps can confidently communicate, and your messaging stays sharp and consistent across every channel. This alignment is one of the critical elements of sales enablement that can significantly impact your success.

Challenge #3: An RFP in sales takes forever to complete

Responding to RFPs should be a strategic sales opportunity. But for many teams, it's a slow, painful process involving dozens of emails, spreadsheets, and review loops.

Salespeople get pulled away from active deals. Subject matter experts lose hours hunting for old responses. And deadlines are missed more often than anyone would like to admit.

The solution: AI RFP software & RFP response automation

Enter RFP solutions and RFP response automation. With AI, you can generate accurate, customized responses in seconds — no more copy-pasting from past documents. Some teams have seen up to 80% of their RFP time freed up, allowing them to focus on what really moves the needle: building relationships and closing business. This efficiency in handling sales RFPs can significantly impact your sales pipeline.

Challenge #4: Personalization at scale feels impossible

Buyers today expect more than a one-size-fits-all pitch. They want to feel like your message was crafted just for them. But when reps are managing multiple accounts or juggling multiple deals, how realistic is that?

The problem is, manual personalization doesn't scale. But skipping it means lower buyer engagement.

Research shows that 71% of consumers expect companies to deliver personalized interactions. And 76% get frustrated when this doesn't happen. Personalization drives performance and better customer outcomes. Companies that grow faster drive 40% more of their revenue from personalization than their slower-growing counterparts.

The solution: AI personalization

This is exactly where AI can step in and assist. With AI sales enablement tools that integrate seamlessly with sales intelligence software, reps can generate messaging that adapts to industry, persona, tone, and even prior prospect interactions. It's the perfect blend of speed and relevance, and it helps your reps connect in a way that feels personal, not templated. Understanding customer preferences and market trends is crucial for effective personalization.

Challenge #5: Too many tools are slowing everyone down

Sales reps today are juggling CRMs, document libraries, chat apps, email, and a number of other tools that are supposedly expected to 'drive' sales productivity. With every tab switch, they lose a little focus and a lot of time.

28% of organizations use 10 or more tools to drive sales productivity, but most are still not happy with their quota attainment and revenue results

Tool overload is one of the silent killers of sales productivity.

The solution: Apps that exist where you work

A comprehensive sales enablement platform that works where your team already does. With AI-enabled platforms that live inside Slack, Microsoft Teams, or your browser, reps can draft emails, find content, or respond to questions without ever switching apps. The result? Faster workflows and more time spent selling. Ensuring smooth technical integrations between these tools is key to maximizing efficiency.

Challenge #6: Collaboration breaks down on complex deals

Big deals often require input from multiple teams — sales, legal, presales, security, and marketing. But aligning all those moving pieces? That's where things fall apart.

Without a shared system, RFP responses get stuck in inboxes, review cycles are chaotic, and final approvals come in late, if at all.

The solution: Streamlined project management

This is where streamlined project management inside your enablement platform can make a huge difference. You can turn messy handoffs into seamless cross-functional collaboration with auto-task creation, review assignments, and progress tracking. Everyone knows who owns what, and nothing slips through the cracks. Effective leadership alignment is crucial to ensure all teams are working towards the same goals.

Challenge #7: Reps don't get the help they need in real time

Let's say a rep is drafting a follow-up email or jumping into a live sales call. They need to answer a tough question or explain a feature clearly, but they're stuck.

Coaching and collaboration might solve this problem — but knowing who to reach out to is an issue. They could ping a colleague or dig through the content portal… or just take their best guess.

The solution: Real-time AI assistance

With AI sales enablement, they don't have to guess. Smart tools can surface the right talking points, pre-approved answers, or context-based suggestions in real time. It's like having a sales coach on-demand, giving reps what they need when they need it most. This just-in-time learning approach, combined with continuous training, ensures reps are always equipped with the latest information.

Challenge #8: You don't know what's working or what's not

You've rolled out new decks, launched a battle card, and trained the team. But, is any of it actually helping?

Without clear sales performance metrics, sales enablement challenges can fly under the radar, and your team might be repeating mistakes you don't even know about.

The solution: Analytics dashboards in knowledge management tools

Look for platforms that provide visibility into what's being used, what's working, and where deals are getting stuck. With data analytics tied to sales content management, RFP output, and usage trends, you can make smarter decisions and prove the ROI of your enablement efforts. Measuring impact is crucial for the continual improvement of your sales enablement strategy. Tracking the right sales enablement metrics could be the key to your success.

Challenge #9: Reps are answering the same questions over and over

Consumers now ask an average of 18 questions during sales calls, up from 13 questions in 2022.

"How long is onboarding?" "Do you integrate with ABC software?" "What's your security policy?"

These questions are important, but answering them over and over is a massive time drain.

The solution: AI sales knowledge management

A central, AI-powered sales knowledge management system changes that. When integrated into daily workflows, reps get quick access to approved, accurate responses that reflect your latest messaging. No more copy-paste from last quarter's doc. It's a major win for sales productivity and buyer engagement, especially in the era of virtual selling.

Challenge #10: Response times are just too slow

If it takes your team three days to reply to a technical question, but your competitor answers in 30 minutes, you're going to lose deals, no matter how great your product is.

Slow response times are often a symptom of all the challenges we've already covered: hard-to-find content, tool overload, and lack of coordination.

The solution: AI RFP response generation

Faster RFP response process with AI. Reps can create complete, on-brand replies in seconds. Whether it's a follow-up email, a questionnaire, or a tricky RFP section, your team stays quick, sharp, and responsive. This improvement in seller performance can significantly impact your win rates.

Turn enablement challenges into revenue wins

As we keep saying, sales enablement isn't just about tools; it's about outcomes. When you solve these sales enablement challenges, you unlock a faster, smarter sales motion. With the help of AI sales enablement platforms, you can cut through the noise, drive real results, and turn your enablement team into a revenue engine.

Whether it's RFP response automation, better sales content management, or improving buyer engagement, the right sales enablement strategy (and the right tech) can transform how your team sells. By focusing on these key areas, you can move beyond traditional sales enablement and embrace revenue enablement, driving growth across your entire organization.