How to Leverage AI to Enhance Sales Enablement

Anand Venkatraman
February 6, 2024
min read

James Bond needs his gadgets. Luke needs the force. A baseball player needs a quality bat. Sales pros need enablement - content, processes, training, coaching and the whole gamut. Reps with sales enablement achieve a 49% win rate on forecasted deals, compared to 42.5% for those without. 

Most organizations have gotten wind of this and now have an enablement function. Highspot’s State of Sales Enablement Report 2023 found that 90% of respondents have a dedicated person, program, or function for sales enablement. The study also points out that this is a 20% increase from last year.

Now, with the arrival of Generative AI, sales enablement is going through a revolution.  The State of AI in Enablement: 2023 Report found that 50% of organizations surveyed currently utilize some type of AI-powered tool in their enablement process. Sales training and coaching, content discovery, selling, and objection addressing are becoming more effective, powered by LLM models, Gen AI predictive analytics, etc. 

For enablement leaders who were long troubled by the hands-on approach to content creation, content management, and distribution, AI is bringing so much respite.  AI in sales enablement has helped streamline content management, produce sales training collateral faster and improve ramp-up times.  

In light of all this, we have written this article to tell you all you need to know about use cases, the benefits and some real examples of AI in sales enablement action.

Traditional Sales Enablement Vs. AI-Powered Sales Enablement

Traditional Sales Enablement AI-Powered Enablement in Action
Approach Generic, one-size-fits-all programs, offering uniform content regardless of individual seller challenges. Personalized and dynamic training tailored to individual sales reps’ performance, strengths, and growth areas, enabled by AI and data analytics.
Content Personalization Limited; content not personalized at scale. Most training is standardized across the board. High; AI facilitates hyper-personalization of training content, aligning with individual sellers’ needs and performance history.
Measurement of ROI Measured by completion of training courses, not by application of knowledge or impact on sales outcomes. Real-time monitoring and adjustment of programs based on metrics like win rates, pipeline generation, ACV value, and customer satisfaction.
Perception by Sales Reps Viewed as a mandatory task, not necessarily connected to actual growth or performance improvement. Regarded as an integral part of daily work, providing targeted guidance and support to improve productivity and deal closure.
Program Adjustment Capability Limited; programs are generally set in advance and not easily adaptable to changing needs or feedback. Dynamic and flexible; AI allows for real-time adjustments and optimization of enablement programs based on ongoing performance data and feedback.

What Current Pain Points & Challenges is AI Solving in Sales Enablement?

Foraging for enablement content

I’ve been there, and I’ve done that. Not as a sales rep. But as part of the demand generation team, creating enablement content is never a challenge. However, making sure sales reps discovered the content was always a challenge. For no fault of their own, most sales reps are left stranded without the right content when the prospect mentions a competitor, and they don’t have the right information to win over the deal. Sales executives cite this as a major concern - (according to G2) 84% feel that content search and utilization are the top productivity improvement area. enterprise organizations lose over $2.3 million each year because of opportunity costs associated with underused or unused marketing content

AI-based sales enablement will help content surface to reps in near-real-time.  In fact, organizations that monitor time spent searching for content report a 3-percentage-point increase in win rates, on average. For example, let's say that prospects mention your competitors on a call or say that they belong to a particular market segment. An AI-integrated sales enablement platform will immediately recommend battle cards and case studies to equip you with talking points against your competitor.

This leads to:

  • Consistent messaging
  • Reduced follow-ups
  • Improved processes for identifying and assessing potential opportunities
  • Enhanced productivity, impact, and involvement with your content
  • Stronger relationships with potential clients, leading to the discovery of new opportunities

Poor content personalization

Personalizing content for sales enablement is hard due to a lack of high-quality customer data, marketing teams and sales teams being at odds in messaging, and inefficiencies in segmentation. The size of the  personalization software market is expected to reach USD 3.93 billion in 2024, and grow at a rate of 20.42% y.o.y to reach USD 12.32 billion by 2030. 

Moreover, personalizing communications at a mass-market level is a problem to do at scale. The bigger the customer base, the harder it is to continuously manage and enrich data, analyze data, create content quickly and ensure quality across all communications.

AI-driven sales enablement makes customer profiling more efficient. AI enables sales pros to better understand prospects’ needs, concerns and objections.  Unlike slow and flawed human effort, AI can analyze data from CRM systems, social media, and website interactions and provide insights into customer preferences, pain points, and buying behaviors, empowering sales reps to create personalized strategies.

This leads to:

- Improved analysis of data from CRM, social media, and website content 

- Improved understanding and empathy for prospects

- Increased engagement

- Strengthened relationships and higher customer satisfaction 

Inability to measure the effectiveness of sales enablement

Many problems - working in silos, incomplete measurement, ineffective communication -  impact the synergy of marketing and sales enablement. One among them is the inability to measure the impact of sales enablement content. According to Sales Enablement Pro, 41% of respondents surveyed are not confident in their ability to prove the impact of sales enablement. Marketers are oblivious to how many conversions their sales enablement content wins over. Generally, these metrics are dependent on the feedback of sales reps.

AI-enabled sales enablement platforms help sales reps track the number of times these assets are recommended and distributed. These tools can deeply integrate their CMS with your email platforms, track distribution bounce rates, and offer follow-up reminders.

Sell confidently with data from over 100+ real time trigger.

How Will AI Change Sales Enablement? 

AI-guided selling is what’s next

B2B buying experiences are becoming more self-serving.  96% of buyers user identify their needs even before they talk to a sales rep. They no longer depend on sales reps to explain features, conduct demos, and understand how they are better than their competitors. 

However, what they need sales reps to do is act as consultants. Buyers want the following information:

1) How will the product benefit their team and business?

2) Are there use cases for the product specific to their industry and pain points?

3) What ROI will the tool bring to their business?

Buyer expectations and, consequently, buyer journeys are changing. Customers despise waiting for sales reps to show product demos.  And this has opened the curtains for the next age of selling.

Enter: AI-guided selling

AI-guided selling, in practice, will look like this. Your sales rep will be on a call selling to a prospect while AI will extract sales-related information across your marketing campaigns, pick up various buyer engagements and provide real-time advice to sellers. 

AI-based sales enablement tools will help sales reps uncover patterns and insights, aiding in the identification of new business opportunities and improving seller effectiveness. Generative AI will also help streamline content creation and tagging, ensuring sellers can access the required content quickly. 


Writers, content marketers, sales enablement pros - blank drafts are intimidating no matter who you are. However, those worries are long gone. 

And unless you live under a rock or are someone like Hemingway, often seeking refuge in remote of the remotest locations to write, you must’ve heard of Gen AI.  Gen AI has permeated public consciousness. It is here to stay. It is dominating all narratives around content creation.

For sales enablement pros, AI will ease how they create content for guidance, training, and coaching. You no longer need to stare at a blank screen to create competitor decks and feature explainers. 

AI can help: 

  1. Brainstorm sales enablement ideas
  2. Generate specific sales enablement content types
  3. Offer examples for sales scripts, battle cards
  4. Personalize pitches

To illustrate, envision a coaching scenario in which you upload a document and instruct the AI to construct a course, a rubric, and responses from the document's content. 

Objections-addressing will become easier

Objection handling is like being a goalkeeper in a high-stakes football game. You must stay focused, prepared to pivot and react to unpredictable shots thrown at you ( minus the privilege of trash talk). 

44% of sales reps fail at objection handling. On average, sales reps handle objections 7 times in a day.  It's unpredictable. It’s draining. And when objections descend into debates, it's simply torturous.  

AI-enabled sales enablement platforms are here to change this. AI analyzes data from past sales, market feedback, and competitor intelligence to predict potential objections, offering real-time, contextually relevant responses. It continually learns and refines its suggestions, ensuring improved performance and personalized handling of objections based on factors like industry and company size.

Sales reps, equipped with AI insights, can swiftly address objections, focusing discussions on solutions rather than lengthy debates. This approach boosts confidence and enhances time efficiency and conversion rates. AI's ability to provide consistent performance support ensures that even less experienced reps can handle objections effectively, leveling the playing field across the sales team.

Make Sales Training and coaching More Engaging & Immersive

AI's role in coaching and training is transformative. It's not about replacing the human touch but enhancing it. Imagine virtual AI sales coaches, a cutting-edge tool in the arsenal of sales enablement. These digital coaches provide a safe, pressure-free environment for reps to practice and perfect their pitches. 

They simulate real-world sales scenarios, enabling reps to refine their skills repeatedly until they feel confident. What's more, these AI coaches offer tailored feedback, pinpointing areas of improvement. This ensures that each rep's unique needs are addressed, fostering a more personalized training experience.

Moreover, AI significantly lightens the load for sales enablement teams. By automating aspects of training and feedback, it frees up valuable time, allowing these professionals to focus on other critical areas of their role. The beauty of AI in sales enablement lies in its ability to blend seamlessly with human coaching, creating a synergistic approach that maximizes efficiency and effectiveness.

Examples of AI for Sales Enablement

Hubspot increased rep productivity and saved $18 million on efficiency savings 

Popular marketing automation platform Hubspot started using AI-based sales enablement technology to manage, organize and govern its sales collateral. Inefficient content discovery processes slowed down Hubspot’s reps - they wasted 5 hours a week searching for the right collateral. After adopting an AI-based sales enablement platform, Hubspot was able to streamline its content management. Overall, this led to each rep saving 2 hours/week and the business getting back $18,000,000 in efficiency savings.

Udemy Uses Conversational Intelligence To Make Better Revenue Decisions

Udemy found collecting insights from sales calls hard. This information gap slowed down ramp-up time. However, new reps were made to listen to live customer conversations while sitting next to the best sellers; hours evaporated in understanding how the best performers talk to customers and what customers say across a sales cycle at scale. 

To solve this, Udemy adopted AI-based sales enablement platforms to gather insights and trends at an account level. Their AI platform analyzed several customer calls and emails, helping sales reps understand customer concerns and identify revenue risks and opportunities. They were able to gather insights from customer interactions at scale. Their AI platform also highlights competitive information for managers when it happens on calls and also allows sales reps to test competitive messaging. 

Top AI Sales Enablement Tools

1. Happysales AI

When it comes to researching and writing personalized emails in seconds, Happysales should be your go-to tool. It allows you to extract prospect information from a large database and effectively reach out to them. 

Key features include

  • Accurate and most updated prospect database 
  • AI-based prediction and suggestion 
  • 100+ company triggers 
  • Auto-generated personalized emails
  • Craft personalized messages based on prospect data, followed by next-step recommendations for reps.
  • Minimize the research time from several hours to less than 30 seconds.

Pricing: Happysales has a forever-free plan that gives you a glimpse of its product capabilities. It has a paid plan that costs $16/month and has unlimited potential.

2. Rafiki

Best for: Managing follow-up messages

Price: $0 to $70 per user/month

Rafiki combines conversation and revenue intelligence features with smart follow-up functionality to help sales reps close deals. Replay sales calls and review AI-powered insights. Then, use the information you glean to send personalized follow-up messages to prospects. Rafiki will even send you real-time alerts when it detects issues, such as ghosted accounts, missed follow-ups, and/or poor sales behaviors that affect company revenue.

Guess what—Rafiki integrates with Close, too. Connect the two apps to help you onboard, ramp, and coach sales reps, while streamlining your team's follow-up procedures.

3. Seismic

Best for: Content analytics and distribution

Price: Contact Seismic for pricing

Want to attract quality leads to your business? Develop an effective content marketing strategy. Want to close more deals than ever before? Teach your sales reps to use the content at their disposal to nudge prospects further into your sales funnel. Seismic was designed to help you with this second task. Easily distribute sales training materials to your reps. Then allow them to distribute sales-related content to potential customers. Seismic will help you determine when to distribute content, too, and even how to improve it, using AI. Sales content optimization has never been this easy, which is why Seismic made this list.

4. Gong

Best for: Detailed sales insights

Price: Contact Gong for pricing

Gong is a popular conversation intelligence app. Like, really popular. The sales enablement tool has over 200k followers on LinkedIn alone. Use this tool to track sales interactions, better understand your target market, and learn how you can improve your company's approach to sales to drive more revenue. From deal execution to sales coaching to forecasting, Gong will elevate your sales department.

5. Highspot

Best for: Boosting team productivity

Price: Contact Highspot for pricing

Last up, Highspot is a sales enablement tool that aims to boost your team's productivity levels to new and exciting heights. Easily store, manage, and distribute sales content. Then, learn which pieces have the biggest impact on your company's bottom line. Highspot can also be used to train new recruits, coach experienced reps, and otherwise teach your sales team to engage prospects in effective ways. The result? More deals, more revenue, more awesome.

Have You Met Happysales AI? 

The MVP of AI in sales is personalized outreach. Meet Happysales which is built to help your sales teams research and write personalized emails in seconds. 

You can easily drive data-backed personalization using 100+ real-time triggers including prospect & company news, tech stack used, funding news, competitor intelligence, persona-specific messaging, and more. 

Happysales does this by splitting up the entire process into four steps;

  • Aggregate: First, the platform automates the collection of data from 650M people and 20M companies, your own CRM data for engagement metrics, and public data sources with unlimited information. This will give you tons of prospects to reach out to. 
  • Transform: Using proprietary AI & ML Models, the platform converts this data into predictions, and recommendations and 100+ AI triggers for real-time monitoring. This ensures a personalized foundation is laid for your next steps. 
  • Personalize: Then AI generates valuable insights, prospect challenges, talking points, recommendations, emails & messages to send at scale.
  • Feedback: Finally, it gathers user feedback to further improve future AI suggestions and predictions so that you can always hit the mark.

With Happsales, you only need 2 minutes to craft the perfect email which makes converting prospects a piece of cake. Are you ready to try it out? Join their waitlist and be the first one to experience the difference of AI in your sales outreach.

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