AI-Driven Buyer Enablement Content: How to Turn B2B Sales Interactions into Deal-Closing Assets

Imagine closing higher-value deals with personalised content at every step of the buyer’s journey. With generative AI in the workflow, this is no longer a resource-intensive undertaking reserved for large teams.

Sales cycles are lengthening, with nearly 90% of B2B buyers reporting a more drawn-out purchase process last year (2023 Global B2B Buyers’ Journey Survey, Forrester).

Yet Gartner revealed that customers who receive helpful information from a supplier were 2.8 times more likely to find purchasing easier and three times more likely to spend more.

Take Troy Munson’s recent success. He closed a $900k deal by building out a digital sales room with relevant content like competitor comparison guides, use cases and blog posts. 

“I continued to pepper them with valuable resources every 2-3 weeks based on previous conversations. It wasn’t pushy. It was helpful.”

It’s a clever strategy, but it raises two critical questions:

  1. How do you know what your customer will actually find helpful? 
  2. How do you create these resources efficiently?

The reality is, buyer enablement content is often lacking. While 71% of B2B buyers consume and share multiple assets during decision-making, many find the content too much of a sales pitch (51%) and not well-catered to their needs (39%) (2023 Content Preferences Survey Report, Demand Gen).

This is where a genAI-enhanced content strategy becomes a game-changer.

With a single sales call transcript, you can create tailored resources for current prospects and any closed-lost deals you feel you should’ve won. Proactively address pain points and objections, make the problem-solution link obvious and simplify the buying process – all while building a library of customer-converting assets.

Let me show you how. 

Here’s a sales call between an online training course creator and a SaaS Learning Management System (LMS). 

We’re going to look at the intel the LMS team can extract from the transcript using generative AI, and how this can inform a buyer enablement content plan that will help close the deal. 

The exchange has been edited for brevity because as you know, sales conversations can sometimes be a long and intricately woven tale of customer woe.

Sales: Thanks for making time to chat today. Could you tell me a bit about your current online courses?

Customer: We’ve been running online courses for three years now and we’re starting to outgrow our current setup – it’s just WordPress with a bunch of plugins. Thinkific has been on our radar but we wanted to explore other options too.

Sales: What challenges are you experiencing with your current system?

Customer: We’re struggling to create interactive content – everything’s a bit static – and we’re feeling limited in how we can track student engagement. Also, our current setup doesn’t allow for different pricing tiers or subscription models, which is becoming a headache as we grow.

Sales: What’s the main goal you’re hoping to achieve by upgrading your e-learning platform?

Customer: I’d say creating more engaging, interactive learning experiences. We also want better insight into how our students are working through the course content. That said, we’re concerned about the potential learning curve and implementation time for a new system. We really can’t afford much downtime. 

Sales: Is there anything else you’re weighing up?

Customer: We’re considering our growth trajectory and need a solution that can scale with us. So pricing structure matters, especially as we expand. 

Sales: Thanks for sharing all that. I can send you some resources that show how Platform addresses many of the issues you mentioned. We can also schedule a detailed walkthrough so you can see how it meets your requirements. Would that be helpful? 

Customer: Yes, that would be great.

Sales: Excellent. I’ll get those details to you now.

AI Prompt: Here is a sales call transcript. What are the customer’s key pain points and objections? What questions need to be answered to convert this customer?

Customer Pain Points

Pain points are the frustrations that drive your customers’ search for better solutions. 

They may not always be explicitly stated, but they’re the fundamental reasons a customer is considering a purchase. If you can show you understand their discomfort, you can position your offering as the salve. 

This customer’s key pain points include:

  1. Outgrowing their current WordPress setup
  2. Difficulty creating interactive content
  3. Limited insight into student engagement 
  4. Lack of pricing model flexibility

Customer Objections

Objections are potholes on the road to conversion – easy to navigate around when you’ve spotted them, a jolting halt to progress when you haven’t. 

Here, customers reveal the concerns that factor into their decision-making. By tackling these head-on, you demonstrate attentiveness to their needs and commitment to their success. If left unaddressed, they become roadblocks on the path to purchase. 

This customer’s main objections have been identified as:

  1. Potential learning curve of a new system
  2. Transition time and possible downtime
  3. Solution scalability and costs as the business grows

Customer Questions

Questions are how your customers investigate the suitability of different solutions. They give you the chance to showcase your expertise and guide their information journey. 

The more questions answered, the greater the customer’s trust in your solution and confidence in their purchase. 

Here’s what the LMS team will need to address to convert this customer:

  • How does the LMS enable the creation of interactive content?
  • What analytics does the LMS offer for tracking student engagement?
  • How flexible is the LMS in terms of pricing models?
  • How does the LMS compare to Thinkific?
  • What is the typical learning curve for new users?
  • How long does migration from WordPress to the LMS usually take?
  • What kind of support and training are available?
  • What does the pricing structure look like for growing businesses?

AI Prompt: What stage is this customer at in the buyer journey and why?

Effective buyer enablement content depends on accurately identifying your customer’s readiness to purchase. Otherwise, it’s like asking someone to join you on a romantic weekend away before you’ve had your first date – your relationship just isn’t there yet. 

This customer is in the consideration stage of the buyer journey. They can clearly articulate their problem and are actively researching solutions, but aren’t yet ready to make a decision. 

AI Prompt: Based on the customer’s buyer journey stage and their identified pain points, objections and questions, please suggest a list of buyer enablement content ideas for each of the following content types:

  1. Solution Briefs
  2. Use Cases
  3. Product Spec Sheets
  4. Case Studies
  5. Competitor Comparisons
  6. FAQs
  7. Blog Posts
  8. Self-Assessments
  9. Value Calculators
  10. Checklists
  11. Roadmaps

To accelerate the LMS team’s sales process for this customer, I’ve identified six priority assets from the generated list.

1. Solution Brief

AI Prompt: Please generate a customised solution brief template that directly addresses the customer’s stated priorities.

A tight two-pager that’s shareable with all decision-makers, a solution brief is particularly useful because it:

  • Summarises how the product addresses the customer’s specific challenges
  • Provides a concise overview of the most relevant product features
  • Positions the product as a comprehensive answer to the customer’s needs

As you map specific pain points to product capabilities, you create content modules that can be mixed and matched to quickly personalise the document for new prospects.

Here’s what a solution brief for this customer should highlight:

  1. Interactive Learning Experiences: Create courses that keep learners motivated and improve completion rates. Showcase multimedia integration, gamification elements, real-world scenario simulations and adaptive learning paths. 
  2. Intelligent Engagement Tracking: Make data-driven decisions to improve course content and student outcomes. Showcase the analytics dashboard, course engagement and completion metrics, individual student progress reports. 
  3. Flexible Pricing Models: Increase profitability with versatile pricing options tailored to customer needs. Showcase pricing tiers and subscription model capabilities, product bundling. 
  4. Simple Implementation: Transition smoothly to a powerful e-learning platform with minimal disruption to your business. Showcase the intuitive interface, straightforward migration process, comprehensive training and support. 
  5. Long-term Value: Maximise ROI with a cost-effective platform that grows with you. Showcase scalable pricing for growing businesses, long-term cost savings compared to current setup, potential for increased revenue through improved features. 

2. Competitor Comparison

AI Prompt: Please list the competitor comparison factors that would be important to this customer. 

Save your prospect the work of preparing a side-by-side themselves and show them how your offering stacks up against the alternatives.

A transparent and thorough competitor comparison:

  • Builds credibility through candor
  • Provides concrete evidence to support the customer’s decision-making process
  • Equips the customer with a tool to discuss and justify their choice with other stakeholders

In this case, the customer would benefit from an LMS vs Thinkific comparison guide. It would directly address their consideration of another platform and highlight LMS strengths in areas the customer cares about.

3. Case Study

AI Prompt: Please suggest three compelling storytelling angles for a case study that would best address this customer’s needs. 

Nothing builds confidence like a success story. And seeing other companies overcome similar challenges with your solution may be the validation your prospect needs to commit.

Much like tailoring a CV for each job application, you can adapt a single case study to highlight different aspects that align with a customer’s unique priorities.

For example, an LMS case study could emphasise how a customer increased course completion rates by adding interactive features or by leveraging student engagement data. Here are a few other angles they could explore for this customer:

  • How They Boosted Course Completion by 40% After Switching to LMS
  • How They Scaled from 1,000 to 10,000 Users in 18 Months
  • How They Doubled Revenue with a Subscription Model

4. FAQs

Every question answered for a current prospect becomes one less query for the next lead. It’s a build-as-you-go knowledge base that serves both sales teams and customers.

While AI can effortlessly generate an extensive list of relevant questions, you’ll want to leverage the expertise of your product and marketing teams to ensure the answers are accurate, informative and engaging.

5. Blog Posts

AI Prompt: Please generate a list of 10 blog post topics that would assist in converting this customer.

The ideas surfaced with this prompt can be used as a springboard for any online media. But I like starting with blog posts as they’re published on your own platform, accessible and discoverable by all potential customers. Their in-depth coverage and singular focus also make them easy to repurpose for other channels like email and social media.

Here are two blog post topics I believe would resonate with this customer. The titles need some refining, but you get the gist.

  1. From Boring to Brilliant: Revamping Your Online Course with Interactive Features to Boost Student Engagement
    This topic speaks directly to the customer’s primary stated problem. It uses emotive language to suggest that the current solution is outdated, which can help drive a sense of urgency for transitioning to a new LMS.
  2. Beyond Completion Rates: Key Metrics Every Course Creator Should Track for Data-Driven Success
    This FOMO-geared topic prompts the customer to question the business impact of their limited analytics. If reporting is a key differentiator for the LMS, this presents an opportunity to highlight the advanced insights available.

6. Roadmap

Roadmaps are an effective way for prospects to visualise the path forward with your solution. By providing a personalised implementation plan, you’re not just selling a product but a partnership, and showing how to turn potential into success.

For this customer, you could create a roadmap titled, “30-Day Plan: Transitioning Your Online Courses from WordPress to LMS”. This would:

  • Directly address concerns about the learning curve 
  • Show that the transition is achievable within a reasonable timeframe
  • Offer a clear, actionable plan to reduce uncertainty
  • Demonstrate the company’s well-defined onboarding process

With limited time and resources, strategy is key. Three questions will help you decide which content to create first for optimal ROI.

Which assets are most likely to convert this customer? 

Content pieces vary in their level of influence on purchase decisions. Focusing on high-impact assets is crucial, especially when you don’t yet have a library to pull from. 

Which assets are easiest for you to produce? 

Adapting existing source material for a customer offers a quicker win than creating content from scratch. This is ideal for time-sensitive sales opportunities where done is better than perfect.

Which assets offer long-term value to your business? 

While being responsive to customer needs is important, creating too many one-time-use assets is a common pitfall. This might be justified for high-value accounts but isn’t always the best use of resources. 

Top-performing content typically:

  • Addresses shared pain points, objections or questions
  • Can be easily adapted, repurposed or scaled
  • Reflects your brand positioning and business objectives

These types of assets help streamline your sales process and benefit multiple customers, offering greater business value.

GenAI can accelerate content creation by producing templates, adapting resources, developing drafts and workshopping titles. But these outputs need refining to ensure alignment with frontline customer insights, core offerings and overall business strategy. 

Once you’ve fine-tuned the content with your team’s expertise, it’s time to put the finished assets in front of your customer. 

What a prospect says and what they do can tell two different stories. Both are essential for an accurate understanding of the buyer and the drivers that will influence deal success. 

Tracking a customer’s interactions with your content through a digital sales room, CRM or email marketing tool unlocks its true value. Your sales process becomes more efficient as you anticipate information needs, identify highly engaged prospects and conduct more timely and targeted discussions.

Using these questions to analyse engagement patterns, you can tailor your sales approach and increase your chances of closing the deal:

  • Which assets are they viewing most frequently? Are we adequately addressing these topics in our conversations?
  • What content are they engaging with between our calls? How does this differ from what we’ve discussed directly?
  • Which of our differentiators are they spending the most time exploring? How can we emphasise these in our next interaction?
  • Which stakeholders are engaging with which assets? What does this reveal about each person’s priorities or concerns?

Leveraging AI for buyer enablement content isn’t just about efficiency – it’s about precision and impact. This approach allows you to:

  • Pinpoint the customer’s buyer stage, pain points, objections and questions
  • Identify content types and topics that will resonate and propel customers through the sales pipeline
  • Create resources that address customer needs and connect the dots back to your business

The result? A streamlined content creation process that produces tailored assets at scale. As B2B sales cycles grow longer, this AI-enhanced content strategy can help create a better buyer experience and close more deals, at higher values.

Keen to explore how this strategy can work for your business? Let’s chat – you can reach me at or LinkedIn.

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