Top Sales Challenges & How AI Can Power Your Sales Enablement

Can you imagine a pilot navigating without a paper map? Or a surgeon operating without proper medical equipment? Of course not. Similarly, sales reps can’t effectively handle sales enablement without proper tools and resources. 

Traditional sales enablement methods, though foundational, often fall short in today’s fast-paced market. They rely heavily on manual processes, leading to inefficiencies and missed opportunities.

Now, Generative AI is transforming sales enablement much like the internet revolutionized the world. According to The State of AI Enablement Report 2023, 50% of respondents’ companies are utilizing some sort of AI tools in their sales enablement processes. 

In this article, we’ll look at the top sales challenges in 2024 and learn how AI can power your sales enablement.

Let’s get started!

What Is A Sales Enablement Strategy?


Sales enablement is all about giving your sales reps tools, training, and resources to crush their sales quotas and achieve organizational goals. But here is the thing- a killer sales enablement strategy isn’t just about throwing a bunch of resources at your team. It’s about providing the right tools and technologies that align with your business structure.

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To close more deals, you need to go inside the customer’s head ( maybe inside their hearts, too) and find out what makes them buy.

Let’s say you sell CRM software. You created buyer personas to help your reps understand the different types of customers they are dealing with—like a marketing manager tired of those ad campaign reports or a sales director obsessed with forecasting accuracy.

Then, you’d arm your reps with targeted resources. You will create content that speaks directly to your target audience’s pain points. You will write strategic emails and attach industry-specific case studies to back your claims.

In short, a sales enablement strategy makes your sales team efficient enough to cease more opportunities faster without losing their mind.

Understanding the Challenges Your Sales Team Is Facing

Before whipping up a killer plan, take a step back and understand the various challenges your sales team is facing: 

Weathering the Economic Storm

The economic climate is no joke. According to a recent report by McKinsey & Company, 82% of sales leaders believe the downturn is making it harder for them to reach their goals. Prospects are tightening budgets, sales cycles are getting longer, and deals are getting smaller.

Even when your team might be working twice as hard to close the deal, it’s only half the size of what they are used to. This is definitely a tough pill to swallow in this challenging economy.

New Buyer Mindset

In 2024, 77% of buyers reported engaging in more complex purchasing processes. Thus, your team should always be ready to adapt to your buyers’ changing needs and expectations.

The shift in the buyer’s mindset impacts the whole funnel. Now, you need more time educating prospects, engaging multiple stakeholders, and creating customized solutions. Building trust and credibility with your buyers takes a lot of sweat and tears.

Bridging the Marketing and Sales divide

When Sales and Marketing teams are on the same page, businesses witness up to 67% successful deals. But the tag of war between marketing and sales is an age-old problem. In 2024, things have gone south. 

Imagine your marketing team creating content that doesn’t quite hit the right chord. Your sales team will keep on struggling to find the right resources to move the funnel. This will further demotivate your team and affect the entire organizational goal.

Standing Out in The Market

With growing VCs and angel funds, industries are growing faster than ever. In this scenario, if you blend in, your business will easily be forgotten.

According to a 2023 survey by Hubspot, 26% of sales professionals mentioned standing out from the competition is one of their biggest challenges. This is due to market saturation, information overload, limited resources, and changing consumer behaviour, making differentiation extremely crucial.

Mastering Social Selling

58.4% of online shoppers purchase at least once every week, and 35% of Americans said social media ads impacted their buying choices. So, social selling is no longer nice to have. According to LinkedIn’s 2024 survey also, 78% of social sellers outperform their peers. However, mastering social selling is not easy.

The primary challenge with social selling is the constantly evolving algorithm of social media. Just when you feel you have cracked the code, the algorithm changes, and your post reach goes down. Providing value through your content is a must to build trust. Only posting is also not enough—engagement is another big part of it. However, a poor implementation strategy harms the process, making social selling harder.  

To tackle these challenges effectively, leveraging advanced technologies can be a game-changer. Let’s explore how AI can power your sales enablement.

How AI Can Power Your Sales Enablement


AI in sales enablement is the process of harnessing the power of advanced technology like machine learning, neural networks, and natural language processing to improve your overall business growth.

Let’s explain how you can utilize the AI to power your sales enablement- 

Intelligent Lead Scoring and Prioritization

Not all leads are equal. Some are good, and some are not worth your time. Prioritization is the way to save time, money, and work energy here.
AI algorithms analyze tons of data from your integrated sources. It scores every lead by considering factors like demographics, behaviour, engagement and firmographic data. This score keeps on updating as new data becomes available.

By prioritizing the leads, sales reps can strain out the leads and get laser-focused on converting them. They can directly address their pain points and come up with customized offers. This targeted approach saves their time and improves their efficiency.

Akkio is one such AI tool for lead scoring. It identifies the high-value leads that you may have overlooked and filters out the unqualified ones, thus shortening your sales cycle and saving you time and, of course, money!

Utilize AI for Predictive Sales forecasting

Decisions like setting quotas, allocating resources, and planning for growth affect the business’s bottom line. Accurate sales forecasting helps businesses make better decisions faster. But if you are following the traditional path, you have to rely on historical data and gut instincts. 
AI can help you eliminate the guesswork in sales forecasting. It analyzes vast amounts of data, including marketing trends, customer behaviour, and sales rep performance, to predict sales with greater accuracy.


According to a Forrester study, an AI tool, Clari, predicted accuracy and helped the sales manager save 80% of their time. This benefited them, worth $2 Million.

Better Communication with AI-Powered Chatbot

The importance of communication has never been this high. Everything is now just a text away. If your business is not, then you’re lagging behind.

AI-powered chatbots are powering up sales enablement by improving communication, enhancing customer engagement and driving better results. The reasons are their 24/7 availability, instance response and consistent, accurate information. AI chatbots can even predict and detect human responses and respond to user emotions. 

An important thing to note here is rule-based chatbots can’t match the efficiency of AI-powered ones as they are more customizable according to your business needs. Their natural language processing ( NLP) can maintain the context throughout the conversation and can be integrated with other sales tools and platforms.

Hubspot is a well-known marketing tool, but you must also check out its chatbot. They can not only handle customer queries, but they can also book meetings and qualify leads. Plus point, you can easily integrate it into your CRM.

AI-Powered Sales Content Personalization

In this competitive landscape, one-size-fits-all content won’t woo your customers. To capture your prospect’s attention and move them through the sales funnel, you need content that speaks directly to their unique pain points and challenges.

In the traditional way, you have less information and crafting personalized content is time-consuming and energy-draining. But equipped with NLP and Machine learning, these AI tools can gather more information from various sources such as CRM, browser history, and social media interaction. With these data, they create tailored content focusing on each customer.

With AI tools like and Jenny AI, you can hyperpolarize your sales content.
Let’s say you are a software company sales rep. You have a lead, Sarah. She has shown interest in your project management tool but hasn’t committed yet.

So, you want to send her an email to convert her. To win her trust, you want to add some relevant case studies as well.

So, here is how can help you:


By delivering hyper-relevant content in real time during the sales cycle, you can significantly increase engagement, build trust, and strengthen your brand image, which results in closing more deals. 

Implement AI-Powered Customer Engagement Analytics

Understanding how your customer engages with your brand across various touch points can smoothen your way to optimize sales and marketing efforts. However, with various channels and data sources, gaining a comprehensive view of your customer engagement can become challenging.

AI algorithms segment your customers based on their behaviour, preferences and engagement level. They can also identify the key moments in the buyer’s journey. With these trends, you can provide personalized recommendations to your customers at every step.

By leveraging AI tools like Mixpanels, Amplitude, and Google Analytics 4, you can better understand your customers’ behaviour. This will allow you to address roadblocks and reduce customer churn proactively.

Use AI for Sales Territory Planning and Optimization

Sales territory planning involves dividing a target market into smaller segments and assigning them to sales resources to optimize productivity and drive growth. 

But creating and optimizing sales territory planning can be a real headache, especially when your team and customer base are constantly growing. AI can swoop in and save the day.

By using AI tools like Salesforce Maps,, and Xactly AlignStar, you can let the algorithm do the heavy lifting. These tools analyze every customer data point to create balanced and efficient territory assignments. 

Brownie points to them for considering factors like travel time, workload balance, and market potential. This means your reps can be more productive, and there is less overlap between territories.

Leverage AI for Real-time Sales Coaching

Sales Coaching is one of the most effective ways to improve sales rep performance. But it is time-consuming, as sales managers already have too much on their plates. But here, AI can be your co-pilot.

AI tools listen to sales calls in recent times and provide real-time guidance to your reps when they need it the most. They can guide them on how to handle objections, ask better questions, and more.

Saleforce’s Einstein Call Coaching is one such AI tool for sales enablement. It not only provides sales coaching but also improves team productivity. Sales managers can access this information faster from the dashboard to guide a newbie sales representative. On the other hand, Sales reps can assess their performance in real-time as well.

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Wrapping Up!

The current sales landscape is tough with economic curveballs, a modern mindset, and fierce competition. But by supercharging your sales enablement with AI, you can blast through those obstacles.

To stay ahead, regularly assess your sales process and point out areas where AI can be leveraged. You alone can not keep up with everything. Train your teams and help them adapt to new technology faster. 

So what are you waiting for? Embrace the power of AI in sales enablement strategy and witness your team soar to new heights!

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