Think about sales enablement like a fresh pair of running shoes for your sales team. They’re ready to sprint toward the finish line faster, but if the fit is off, so are the results.
On paper, sales enablement promises speed, efficiency and better outcomes. But if your tools, tech and processes aren’t thoughtfully chosen and strategically implemented, they can end up slowing everyone down. Instead of empowering your sales team, you’re left with friction that costs time and leaves money on the table.
On the flip side, a highly strategic sales enablement approach gives sales teams valuable insights, streamlines the sales cycle and offers an edge against competitors.
When it comes to hitting your stride in the race to close more deals faster, here are five common challenges in sales enablement and practical ways to overcome them.
1. Investing in Sales Enablement Software Without a Plan
When sales leaders are under pressure to hit ambitious targets, it’s tempting to jump at the latest sales enablement tools on the market. A slick demo or bold promise of “improved outcomes” can feel like the solution you’ve been searching for. Without a plan, though, even the most impressive software can derail your efforts.
Sales enablement depends on a stack of tools working together. From the CRM that serves as your foundation to CMS platforms and sales analytics tools, each must integrate with the others to avoid creating silos. Without this alignment, you’ll encounter:
- Data bottlenecks that force reps to work across multiple systems
- Inconsistent reporting that muddies your ability to measure ROI
- Frustrated salespeople who abandon tools that slow them down
Create a cohesive strategy before you invest. That means mapping how each tool will support your process, confirming integrations are airtight and planning for sales training.
A key part of that training plan is identifying a champion within your sales team — someone who can learn the system inside and out, model best practices and coach others along the way. When peers see a colleague successfully using a tool, adoption feels less like a top-down mandate and more like a proven path to better results.
It’s worth noting that AI and large language models (LLMs) can amplify the sales coaching process. Through real-world simulations, sales reps can practice handling objections, refine discovery questions and get real-time feedback in a safe environment.
2. Leveraging Outdated Sales Enablement Content
Sales enablement lives and dies by content. Case studies, one-pagers, guides, ROI calculators, email templates and playbooks can make the difference between a rep moving a deal forward or losing momentum with a buyer. But when this content is outdated or irrelevant, it becomes a liability.
Imagine a prospect receiving a case study with data from five years ago, or worse, an email template that references a product your company no longer offers. Outdated content undermines credibility and wastes valuable time in the sales cycle. That’s why it’s vitally important to:
- Audit your library regularly to catch inaccuracies or gaps
- Sunset old assets that no longer reflect your brand or offerings
- Map each asset to the buyer’s journey to guarantee full coverage
Equally important is accessibility. Sales teams shouldn’t have to dig through folders or outdated drives to find what they need. Creating a centralized, easy-to-use hub means reps can spend less time searching for the information they need and more time selling.
Increasingly, AI helps standardize the messaging around these assets, while leaving room for personalization. In HubSpot, built-in customizable playbooks unify language around discovery, pricing, competitor comparisons and objection handling. You can even train AI agents on these playbooks, so reps get answers to consistently qualify leads.
For more insights into how AI is revolutionizing sales enablement, see this blog post.
3. Failing To Align Marketing and Sales Teams
If sales and marketing departments feel like they’re at odds, buyers will feel the disconnect, too. Friction between these two groups often stems from misaligned expectations: marketing feels sales isn’t closing leads; sales feels marketing isn’t generating enough qualified leads. What buyers are left with is a disjointed experience.
Bridging the gap between marketing and sales requires cultural and technical alignment. Service-level agreements (SLAs), shared KPIs and regular joint meetings can help both teams understand each other’s responsibilities and progress.
Meanwhile, your CRM can become a bridge rather than a barrier. Tagging feedback directly in the CRM, for instance, allows marketing to see exactly what sales reps are hearing in the field and respond with updated content, new messaging or improved processes. Shared reporting dashboards further strengthen alignment, as the two teams are looking at the same data — from pipeline health to campaign performance — and can see what’s working, what’s not and where adjustments are needed.
With tools like HubSpot, you can layer in AI-powered lead scoring that analyzes recent interactions to predict which prospects are most likely to engage. This helps prioritize outreach and ensures both teams focus on the right opportunities at the right time.
When sales and marketing speak the same language and share the same tools, they create a strong, more collaborative process that the buyer ultimately feels.
4. Not Taking Feedback Seriously From the Sales Process
Too often, sales feedback never makes it past a pipeline review. Reps stop using assets or tools they feel aren’t working, but fail to communicate why. Or, when they do share input, it’s met with frustration or ignored by leadership. Over time, this discourages reps from speaking up at all.
The reality is that sales teams have a front-row seat to buyer objections, pain points and decision-making behaviors. Ignoring their feedback means missing critical opportunities to refine your sales enablement strategy.
If reps report that buyers consistently hesitate over pricing, marketing can respond by creating ROI-focused calculators, case studies or comparison guides that demonstrate value in concrete terms. These sales and marketing materials can help reps confidently counter objections and reassure prospects that the investment will pay off.
If sales identifies a specific type of content — say, a customer testimonial video or industry-specific case study — that consistently helps win deals, that’s a clear signal to double down. Marketing can replicate the format, expand it across more verticals and make sure it’s easily accessible to every rep.
The key, as alluded to above, is to create a feedback loop that closes the gap between sales and the rest of the organization. When reps see their feedback turned into action, adoption increases and enablement strategies become more effective.
5. Misdiagnosing the Cause of Lead Loss
When deals fall through, it’s natural to jump into fix-it mode: spend more on lead acquisition, hire new reps or replace underperforming tools. These fixes waste precious resources, though, if you don’t understand the underlying cause of lead loss.
A more effective solution starts with digging into quantitative and qualitative data. CRM reports can show you exactly where prospects are dropping off, while follow-up interviews with lost leads can reveal the “why.” Often, the causes are surprisingly simple.
For instance, buyers may often start excited but stall once they need proof points: ROI, customer outcomes or comparisons to alternatives. If your content library doesn’t fill those needs, sales may struggle to keep momentum. Creating stage-specific resources, like industry benchmarks or customer success snapshots, can give buyers confidence to progress.
By pinpointing the exact friction points, you can intervene strategically to amplify sales performance, whether that’s creating new content, improving follow-up timing or refining lead nurturing workflows. Diagnosing before prescribing keeps sales enablement solutions targeted, cost-effective and impactful.
Accelerate Your Sales Enablement Success With a Partner Who Knows It Best
Make better use of your sales enablement technology by setting up integrations and workflows that support your reps. Develop collateral for every buyer at every stage. Train your team consistently so best practices become second nature. These are the steps that keep your team in shape and ready for the long haul.
We know tackling these sales enablement challenges can feel like a lot on your own. Kuno is in your corner.
We guide companies through every stage of sales enablement, combining inbound strategies with tailored toolkits, buyer journey mapping and continuous optimization.
Like a new pair of running shoes, we move with you in stride every step of the way, helping your team find its rhythm, build endurance and finish ahead of the competition.
Let’s talk about how we can help your team go the distance.
