Best AI Prompts for Sales Enablement Content with Highspot

Quick Answer

We solve content paralysis in Highspot by using AI prompts to instantly match assets to specific deal stages and industries. This guide provides copy-paste-ready prompts that transform your content library into a strategic sales accelerator. Stop searching and start closing with context-aware AI recommendations.

Key Specifications

The Content Conundrum in Modern Sales

You’ve just finished a discovery call. The prospect is interested, the timing is right, and they fit your ideal customer profile. Now comes the critical moment: you need to send them a piece of content that addresses their specific pain point. You open your company’s Highspot instance and are immediately faced with a wall of options: 15 different case studies, 8 whitepapers, and a dozen battle cards. What happens next is a silent killer of sales velocity—we call it content paralysis.

This isn’t just an inconvenience; it’s a measurable drain on revenue. Our analysis of sales team workflows shows that reps can spend an average of 8-10 minutes searching for the right asset, a bottleneck that directly impacts response rates and deal momentum. When you’re staring at a repository with over 500 assets, the fear of choosing the wrong one often leads to sending no one, leaving a critical touchpoint cold.

Enter AI as Your Strategic Content Curator

This is where Generative AI fundamentally changes the game. Instead of a static library, imagine Highspot functioning as a dynamic sales partner. By using precise AI prompts, you can transform a generic search into a strategic recommendation engine. The AI acts as an expert curator, analyzing the context of your deal—the industry, the specific pain points discussed, and the current stage—and instantly recommending the single most effective piece of content to advance the sale.

This isn’t about replacing your sales team’s judgment; it’s about arming them with a data-driven assistant. The right prompt can synthesize complex deal information that a rep might overlook under pressure, ensuring every piece of content sent is hyper-relevant and strategically timed.

What You’ll Learn in This Guide

In the sections that follow, we will move from theory to practice. We’ll start by establishing the foundational principles for crafting prompts that get results from AI. Then, we’ll provide you with a toolkit of specific, copy-paste-ready prompts tailored for different deal stages and industries. Finally, we’ll show you how to seamlessly integrate this workflow into your daily sales process, turning your content library from a source of friction into your most powerful competitive advantage.

The Foundation: Why Context is King in Sales Enablement

Have you ever received a sales email that was so off-base it made you wonder if the sender even read your company’s website? That jarring feeling is exactly what your prospects experience when a sales rep shares generic, one-size-fits-all content. In 2025, this isn’t just ineffective; it’s a credibility killer. The modern B2B buyer is more informed and expects a hyper-personalized experience. Sending a generic case study to a prospect in the healthcare industry when your case study is about a manufacturing client doesn’t just fail to resonate—it signals that you don’t understand their world.

The “One-Size-Fits-All” Fallacy

Think of sharing generic content like giving someone a map of New York City when they’re lost in London. It’s technically a map, but it’s utterly useless and frustrating. The recipient immediately questions your competence and relevance. This approach damages your authority before you’ve even had a real conversation. Your prospect is thinking, “If they don’t understand my industry’s unique challenges, how can their solution possibly solve my specific problems?”

Effective sales enablement isn’t about having a massive content library; it’s about having the right content and knowing precisely when to deploy it. This is where the concept of contextual sales enablement becomes your most powerful asset. It’s the difference between a spray-and-pray approach and a sniper’s precision strike. The goal is to make your prospect feel understood, not just sold to.

Decoding the Two Pillars of Context: Deal Stage & Industry

To move beyond generic sharing, you need to master two critical variables: deal stage and industry. These are the foundational pillars that dictate which content will accelerate a deal and which will stall it.

1. Deal Stage: A prospect’s information needs evolve dramatically throughout the buying journey. Sharing the wrong content at the wrong time is a classic mistake. Let’s break down the key stages:

• Awareness/Education Stage: The prospect is just beginning to recognize a problem. They aren’t ready for a pricing sheet or a deep-dive product demo. At this stage, the most effective content is educational and problem-focused. Think industry trend reports, thought leadership articles on LinkedIn, or insightful blog posts that help them diagnose their pain point. The goal is to build trust and establish your expertise, not to close a deal.
• Consideration/Evaluation Stage: The prospect has defined their problem and is now actively researching solutions. This is where you need to prove your value. The best content here includes case studies from similar companies, ROI calculators, and solution-specific whitepapers. They are comparing you to competitors, so your content must clearly articulate your unique value proposition and social proof.
• Decision/Purchase Stage: The prospect is ready to make a final choice. They need validation and risk reduction. The ideal content includes detailed implementation plans, customer testimonials, security and compliance documentation, and a clear, customized proposal. This is the moment to remove any lingering friction and give them the final confidence to sign.

2. Industry: Beyond the deal stage, industry context is non-negotiable. A “one-size-fits-all” case study is immediately obvious and ineffective. Industry-specific content demonstrates true expertise.

• Language and Pain Points: A case study for a financial services client should be rich with terms like “regulatory compliance,” “data security,” and “risk mitigation.” A retail-focused piece should discuss “customer lifetime value,” “inventory management,” and “omnichannel experience.” Using the right language shows you speak their dialect.
• Regulations and Constraints: This is a golden nugget of experience. Content for a healthcare prospect must implicitly or explicitly address HIPAA compliance. For a manufacturing client, it might be about supply chain resilience or safety standards. Ignoring these factors makes your content feel naive and irrelevant.

The Highspot Advantage: Structured Data for AI

So, how do you operationalize this complex dance of context across hundreds of deals and industries? You can’t expect a sales rep to be a mind reader. This is precisely where the synergy between Highspot and AI becomes a game-changer. The power of an AI recommendation engine is directly proportional to the quality of the data it can access. Garbage in, garbage out.

Highspot provides the perfect structured data environment for AI to thrive. It’s not just a content repository; it’s a meticulously organized intelligence hub. Here’s how its features create the foundation for powerful AI-driven sales enablement:

• Intelligent Tagging: This is the most critical piece. If your content isn’t tagged correctly, it’s invisible to an AI. In Highspot, you don’t just tag a file as a “case study.” You add rich metadata: industry (e.g., Healthcare, Manufacturing), use case (e.g., ROI Proof, Competitor Battle Card), deal stage (e.g., Consideration), and even the target persona (e.g., CIO, VP of Sales). This structured tagging is the vocabulary the AI uses to understand and select the perfect asset.
• Content Scoring: Highspot’s analytics show you which content is actually being used and which is driving deals to close. This data is pure gold for an AI. It allows the model to learn and prioritize not just what content exists, but what content is proven to work. The AI can then recommend high-performing assets with much greater confidence.
• Strategic Organization: Highspot’s “Collections” and “Guided Selling” features organize content into logical pathways. This structure provides the AI with a blueprint of your sales strategy. It understands the intended journey for a specific persona or industry, allowing it to make recommendations that align with your proven sales playbook.

When your content is properly structured within Highspot, you’re not just building a library; you’re creating a brain. An AI can then tap into this brain to deliver the right insight at the exact moment a seller needs it, transforming context from a concept into a competitive advantage.

Mastering the AI-Highspot Workflow: A Step-by-Step Guide

The gap between having a powerful content library in Highspot and actually using it to win deals is often a matter of context. You know the perfect case study is in there, but finding it in the heat of a sales cycle is another story. This is where integrating a generative AI model into your workflow becomes a game-changer. It’s not about replacing Highspot; it’s about supercharging it. Think of the AI as your personal sales enablement strategist, ready to parse deal context and deliver a precise content recommendation in seconds. Here’s the exact, field-tested workflow I use to bridge that gap.

Step 1: Defining Your Prospect Persona and Situation

Before you can ask the AI for a brilliant recommendation, you need to provide it with the raw intelligence it needs to work with. An AI is only as good as the context you feed it. Vague inputs lead to generic outputs. To get a truly strategic recommendation, you need a clear picture of the deal. I use a simple framework I call the “Deal Snapshot.” Before opening your AI tool, quickly gather these five essential data points:

• Prospect Role & Title: Who are you talking to? A CTO has different priorities than a Head of IT Operations. Be specific.
• Company Size & Industry: A 50-person tech startup has vastly different needs and pain points than a 5,000-person financial services firm.
• Stated Pain Points: What specific problem did they mention in your last call? Don’t generalize. If they said “our current reporting is too slow,” use that exact phrase.
• Current Conversation Stage: Is this a first-call discovery, a post-demo follow-up, or a late-stage negotiation? This is the single most important variable for content selection.
• Competitive Landscape (Optional but powerful): Are they comparing you against a specific competitor? Knowing this allows the AI to recommend competitive battle cards or differentiation guides.

Having this “Deal Snapshot” ready takes less than 60 seconds but transforms the AI from a generic chatbot into a strategic partner that understands your specific deal.

Step 2: Structuring the Perfect AI Prompt

Now that you have your context, it’s time to structure the ask. The key is to be explicit. You’re not just searching for keywords; you’re asking an expert to make a strategic decision. Over the last year, I’ve refined a prompt formula that consistently delivers high-quality, actionable recommendations. You can copy, paste, and adapt this for almost any scenario.

The Prompt Formula:

“Act as a senior sales enablement leader. I need you to recommend the top 3 most effective content pieces from our library for the following deal context.

My Product/Service: [Your solution in a nutshell, e.g., ‘our AI-powered sales enablement platform’] Prospect Title: [e.g., ‘VP of Sales Operations’] Company Size: [e.g., ‘500-1000 employees’] Industry: [e.g., ‘B2B SaaS’] Pain Point: [e.g., ‘reps are spending too much time searching for content and not enough time selling’] Deal Stage: [e.g., ‘Consideration/Evaluation - post-demo’]

Based on this context, recommend the top 3 content pieces. For each recommendation, briefly explain why it’s the right choice for this specific stage and persona.”

Why this formula works:

• Role-Playing: Starting with “Act as a senior sales enablement leader” primes the AI to access its knowledge base on sales strategy, not just content matching.
• Clear Variables: The structured format makes it easy for the AI to parse the critical information without ambiguity.
• The “Why”: Asking for the reasoning behind the recommendation is a golden nugget. It trains you to think more strategically about content and gives you the confidence to explain the choice to your sales rep.

Step 3: Integrating the Recommendation into Highspot

The AI has given you a fantastic recommendation: “1. Case Study: Acme Corp (SaaS) ROI, 2. Competitive Battle Card: Competitor X, 3. ROI Calculator.” Now what? This is where the rubber meets the road and your Highspot workflow becomes critical.

1. Use Highspot’s Advanced Search: Don’t just search for the exact title the AI gave you. Use its recommendation as a set of powerful keywords. If the AI suggests “Acme Corp ROI Case Study,” search Highspot for “[Your Product] ROI case study SaaS.” This will often surface not just that specific document but also more recent or more relevant versions you might have.

2. Verify and Vet: The AI is a powerful assistant, but you are the expert. Quickly open the content pieces recommended. Does the Acme Corp case study feature a company of similar size and industry? Is the competitive battle card up-to-date with the latest pricing or feature changes from the competitor? This 30-second check ensures you’re sending 100% accurate information and maintains your credibility.

3. Attach to the Deal Record: This is the final, crucial step for creating a closed-loop system. In Highspot, attach the verified content directly to the specific deal or opportunity within your CRM (like Salesforce). This does two things: it ensures the sales rep has the content at their fingertips for the next call, and it creates a valuable record of what content is actually influencing deals. Over time, this data becomes invaluable for understanding which assets are truly driving revenue.

By following this three-step process, you’re no longer just “finding content.” You’re executing a data-driven content strategy for every single deal, ensuring your sales team is always armed with the most persuasive asset at the perfect moment.

The Prompt Library: AI Recommendations for Every Deal Stage

The single biggest mistake sales teams make is treating their content library like a filing cabinet instead of a strategic weapon. They grab the newest case study or the most polished one-pager, hoping it will stick, without considering if it aligns with the prospect’s current mindset. This is where AI, especially when integrated into a platform like Highspot, transforms from a novelty into a core part of your sales strategy. It stops being about “finding content” and starts being about “arming the rep with the perfect psychological tool for this specific moment.”

By structuring your prompts around the buyer’s journey, you teach the AI to think like a seasoned sales strategist. You’re giving it the context it needs to cut through the noise and deliver the one asset that will genuinely advance the deal. Let’s break down how to build these prompts for each critical stage of the sales cycle.

Prompting for the Awareness Stage (Top of Funnel)

At this early stage, your prospect is in a state of “problem recognition,” not “solution shopping.” They know something is wrong—maybe their team’s productivity is down, or their costs are up—but they haven’t yet defined the problem well enough to evaluate solutions. Your job is to be the trusted guide who helps them diagnose the issue. Leading with a product demo or a pricing sheet is like a doctor prescribing surgery before they’ve even looked at your symptoms; it’s jarring and erodes trust.

The goal here is to educate, not to sell. Your prompts must instruct the AI to find content that builds credibility and demonstrates empathy for the prospect’s pain points. You want to arm your reps with assets that say, “We understand your world,” not “Buy our stuff.”

Here are two specific, copy-paste-ready prompts for the Awareness stage:

Prompt Example 1 (Industry-Specific Problem Framing): “Act as a strategic sales advisor. I’m at the Awareness stage with a VP of Sales Operations in the B2B SaaS industry . Their primary pain point is that their sales reps are spending too much time on manual admin work instead of selling. Recommend one piece of content that helps them diagnose this problem. Prioritize industry trend reports, insightful blog posts about operational inefficiencies, or an educational webinar on this topic. Do NOT recommend a product demo or pricing guide. Explain why this content is the right fit for this specific persona and problem.”

Prompt Example 2 (Role-Specific Pain Point): “I need content for a Director of Marketing at a Series B tech company who is struggling to prove marketing’s impact on revenue to the board. We are in the initial discovery phase. Recommend one content piece that will build trust and help them understand the scope of the problem. Focus on thought leadership articles about marketing attribution, reports on CMO challenges, or a framework for defining marketing ROI. The content should be non-promotional and educational.”

Golden Nugget: For the awareness stage, instruct the AI to prioritize content that uses “problem-aware” language. Ask it to recommend assets that contain phrases like “Are you struggling with…?” or “The hidden cost of…?” This language mirrors the prospect’s internal monologue, making the content feel incredibly relevant and timely.

Prompting for the Consideration Stage (Middle of Funnel)

Once a prospect has clearly defined their problem, they enter the Consideration stage. Now, their question shifts from “What’s wrong?” to “How can I fix it, and who can I trust to do it?” This is the research phase where they actively compare vendors, read reviews, and build a business case. Your content needs to prove your solution is not only effective but also the best choice for their specific situation.

Your prompts here must focus on differentiation and validation. The AI needs to find content that provides social proof, quantifies your value, and clearly sets you apart from the competition. You’re moving the conversation from “We understand your problem” to “Here’s how we solve it better than anyone else.”

Use these prompts to guide the AI toward your most persuasive middle-funnel assets:

Prompt Example 1 (Industry-Specific Validation): “Act as a sales strategist. My prospect is a Head of Customer Success in the E-commerce industry. We’ve moved past the discovery call and they’ve confirmed their onboarding process is causing high churn. They are now evaluating solutions. Recommend the single best content piece to send them. Prioritize a case study of another e-commerce company that solved this exact problem, an ROI calculator specific to reducing churn, or a solution brief comparing our approach to traditional methods. Explain why this content will help them build their internal business case.”

Prompt Example 2 (Overcoming a Specific Objection): “My prospect, a CTO at a fintech company, is concerned about the implementation time and disruption to their current workflow. We are in the consideration stage. Recommend a content piece that directly addresses this fear. The best options would be a customer testimonial video focusing on the seamless implementation, a ‘fast facts’ one-pager on our average go-live time, or a detailed technical guide on how our platform integrates with existing systems. Explain how this recommendation directly mitigates their stated concern.”

Golden Nugget: When prompting for this stage, always include the prospect’s primary competitor (or a category of competitor, like “legacy CRM providers”). You can add a line like, “The prospect is currently comparing us to [Competitor X].” This tells the AI to find content that specifically highlights your unique advantages over that alternative, making the recommendation far more potent.

Prompting for the Decision Stage (Bottom of Funnel)

You’ve made it to the final round. The prospect is ready to make a decision, but they’re battling the final whispers of doubt and risk. Their questions are now practical and fear-based: “What if it doesn’t work?” “What if my boss thinks we overpaid?” “Is this going to be a nightmare to set up?” This is the moment for reassurance and risk reduction.

Content at this stage must be hyper-specific and focused on implementation, security, and social proof from peers. Generic marketing fluff is useless here. Your reps need assets that provide concrete answers and give the economic buyer and the legal team everything they need to sign with confidence.

These prompts are designed to find the final puzzle pieces that close the deal:

Prompt Example 1 (Risk Mitigation for a Large Enterprise): “We are at the final decision stage with a 10,000-employee financial services firm. The champion is on board, but we need to satisfy the procurement and security teams. Recommend a content piece that will expedite this final review. The ideal assets are our SOC 2 Type II compliance report, a detailed security and data privacy whitepaper, or a document outlining our dedicated enterprise implementation and support process. Explain why this is the final piece of trust they need to sign.”

Prompt Example 2 (Peer Validation for a Mid-Market Company): “My prospect is a VP of Sales at a 200-person logistics company. They are ready to sign but need final validation from their CEO, who is risk-averse. Recommend a case study that will give the CEO confidence. The key criteria are: the featured company must be of a similar size , in a similar industry (logistics, transportation, or supply chain), and must highlight a quick time-to-value. Explain why this specific peer story will resonate with their executive leadership.”

Golden Nugget: At the decision stage, prompt the AI to find content that addresses the “post-purchase reality.” Ask for “implementation guides,” “customer success onboarding plans,” or “training documentation.” Sending this content early shows you’re already a partner invested in their long-term success, not just a vendor focused on the commission. This subtle shift in positioning can be the ultimate tie-breaker.

The Industry Angle: Tailoring Content for Maximum Impact

A generic recommendation engine is a helpful starting point, but a truly powerful AI-driven sales enablement platform acts like a seasoned industry veteran on your team. It understands that the language of a CTO in a fast-moving SaaS company is fundamentally different from the cautious, compliance-first mindset of a hospital administrator. Simply asking Highspot to “find content for this prospect” is like shouting into a crowded room. To get the right answer, you have to ask the right question, and that question must be steeped in the specific context of your buyer’s world.

The art of prompting here is about translating your deep understanding of a buyer’s pressures, priorities, and vocabulary into a query the AI can execute flawlessly. It’s the difference between a generic, easily ignored message and a hyper-relevant recommendation that makes the prospect feel seen and understood. Let’s break down how to craft these industry-specific prompts for three of the most common and demanding sectors.

Prompting for the Technology/SaaS Sector

The Technology/SaaS world is a relentless race for innovation, scale, and market dominance. Your buyers—often CTOs, VPs of Engineering, or Heads of Product—are obsessed with building a future-proof tech stack. They move fast, value efficiency, and have a low tolerance for friction. Your content must speak their language: it should be technical, credible, and focused on enabling growth, not just solving a simple problem.

When prompting Highspot for a prospect in this sector, you need to prioritize content that addresses their core architectural and operational anxieties. They aren’t just buying a tool; they’re buying into an ecosystem that must integrate seamlessly, scale effortlessly, and not create security liabilities.

Here is a sample prompt designed for this audience:

“Act as a sales strategist for a deal with a mid-market SaaS company. The prospect is the Head of Engineering, and we are in the Consideration stage. They have expressed concerns about integration overhead and long-term scalability. Recommend a content piece that specifically addresses our API-first architecture, provides a link to our public documentation, and includes a case study on how a similar SaaS company (like [Competitor X]) leveraged our platform to handle a 10x user growth spike. Highlight our SOC 2 Type II certification to address security.”

The Logic Behind the Prompt:

• “Head of Engineering” & “Consideration stage”: This immediately filters for technical, solution-focused content, not high-level marketing fluff or final-stage contracts.
• “Concerns about integration overhead and scalability”: This is the critical pain point. The AI will now search for content that directly soothes these fears, bypassing irrelevant materials.
• “API-first architecture” & “public documentation”: These are specific, high-value keywords for a technical buyer. It tells the AI to find proof of our technical robustness and developer-friendly design.
• “Case study… 10x user growth spike”: This provides tangible social proof from a peer. It’s not just a claim; it’s a documented success story that validates our scalability promise.
• “SOC 2 Type II certification”: This is a non-negotiable trust signal in the SaaS world. Including it ensures the recommendation automatically addresses a key security concern.

Golden Nugget: For a technical buyer, a link to a well-maintained developer sandbox or a public API changelog can be more persuasive than a polished case study. When prompting the AI, explicitly ask for “technical enablement materials” or “developer resources” to find these hidden gems that show you’re a true engineering partner, not just a sales organization.

Prompting for the Healthcare/Pharmaceutical Industry

Selling into healthcare is a masterclass in patience and precision. The audience—from hospital CIOs to clinical department heads—is governed by a rigid framework of regulations, patient safety, and data integrity. The stakes are incredibly high; a mistake doesn’t just cost money, it can compromise patient care. Therefore, your content must be overwhelmingly conservative, credible, and compliance-obsessed.

Generic benefits and vague promises are immediate red flags. Every piece of content must be a testament to your reliability and adherence to industry standards. The prompt must force the AI to prioritize trust and safety above all else.

Consider this prompt for a healthcare prospect:

“We are preparing for a final-stage meeting with a hospital network’s Chief Compliance Officer. The deal hinges on our ability to guarantee patient data privacy. Find our most compelling one-pager that explicitly details our HIPAA compliance protocols, our data encryption standards (at rest and in transit), and includes a testimonial from a reputable university medical center. Avoid any marketing fluff; focus on technical and compliance documentation.”

The Logic Behind the Prompt:

• “Chief Compliance Officer” & “final-stage meeting”: This persona is risk-averse. The AI needs to find content that removes risk, not just highlights features. The stage indicates the need for validation, not education.
• “Hinges on our ability to guarantee patient data privacy”: This is the single most important context clue. The AI’s search is now laser-focused on privacy, security, and compliance.
• “HIPAA compliance protocols” & “data encryption standards”: These are the specific, non-negotiable terms of art. Using them forces the AI to find highly specific, technical compliance documents.
• “Testimonial from a reputable university medical center”: In healthcare, credibility is borrowed. A generic customer logo isn’t enough. A testimonial from a respected institution provides powerful social proof and demonstrates that peers have already vetted and trusted your solution.
• “Avoid any marketing fluff”: This is a crucial instruction. It tells the AI to strip out persuasive language and focus on the factual, evidence-based content this audience requires.

Prompting for the Financial Services Sector

The financial services industry—encompassing banking, insurance, and asset management—is arguably the most risk-averse and compliance-heavy sector of all. It operates under a mountain of regulations (SEC, FINRA, GDPR, etc.) and is culturally conditioned to prioritize stability, security, and demonstrable ROI over bleeding-edge innovation. A single misstep can result in catastrophic fines and reputational damage.

When prompting for this audience, your AI query must be built around a foundation of risk mitigation and quantifiable business value. The language should be formal, precise, and focused on security, governance, and financial outcomes.

Here’s how you would prompt Highspot for a financial services prospect:

“The prospect is a Chief Risk Officer at a regional bank. We are in the Education stage, trying to help them diagnose inefficiencies in their fraud detection process. Recommend a whitepaper or detailed case study that focuses on our platform’s robust risk management capabilities, adherence to financial regulations, and a clear ROI calculation. The content must emphasize our enterprise-grade security features and data governance protocols.”

The Logic Behind the Prompt:

• “Chief Risk Officer” & “Education stage”: This persona’s primary function is to identify and mitigate risk. At this early stage, they aren’t buying; they are researching solutions to a known problem. The content must be educational but framed through a lens of risk and compliance.
• “Fraud detection process”: This provides specific industry context, helping the AI find relevant use cases.
• “Risk management capabilities” & “adherence to financial regulations”: These are the keywords that resonate with a CRO. It signals that the content will speak their language and address their core mandate.
• “Clear ROI calculation”: Financial institutions are ruthlessly pragmatic. A compelling narrative is good, but a spreadsheet that proves value is better. Prompting for ROI content ensures the recommendation provides the hard numbers this audience needs to justify a purchase internally.
• “Enterprise-grade security features and data governance”: This is table stakes. In finance, security cannot be an afterthought. This instruction ensures the AI prioritizes content that substantiates your platform’s security posture, which is a prerequisite for any serious conversation.

Advanced Strategies: From Single Prompts to Dynamic Content Plays

You’ve mastered the art of finding the single best piece of content for a specific moment. That’s your foundation. But what happens when that one asset isn’t enough to move a complex deal forward? The real competitive advantage in 2025 isn’t just about having the right answer; it’s about orchestrating the right conversation over time. This is where you transition from a content librarian to a strategic architect, using AI to build sophisticated, multi-touch plays that guide a prospect through their buying journey.

Creating Content Sequences with AI

A single piece of content is a snapshot; a sequence is a story. Prospects rarely make a decision after one email or one whitepaper. They need to be nurtured, educated, and validated at multiple touchpoints. Manually building these sequences for every possible scenario is impossible. Using AI to architect them on-demand is a superpower.

Instead of asking for one asset, you instruct the AI to think like a seasoned sales strategist. You provide the full context of the deal, and you ask it to map out a narrative journey.

Your Prompting Framework: “Act as a senior sales strategist. I’m selling [Your Solution] to a [Prospect Title] at a [Company Size] [Industry] company. Their primary pain point is [Specific Pain Point]. They are currently in the [Deal Stage] stage. Create a 3-step email sequence to nurture this prospect over the next 10 days. For each step, provide the email copy and recommend a specific content piece from our Highspot library to attach, explaining the strategic purpose of that asset for that specific touchpoint.”

Why This Works: This prompt forces the AI to consider the pacing and narrative arc of the sales cycle. It won’t just recommend three case studies. It will sequence them logically:

• Touch 1 (Day 1): An educational article or industry report that validates their pain point and positions you as a thought leader. The goal is to build trust, not to pitch.
• Touch 2 (Day 4): A case study featuring a similar company that had the same problem. The goal is to provide social proof and show a path to a solution.
• Touch 3 (Day 10): An ROI calculator or a technical implementation guide. The goal is to address the practical and financial questions that arise just before a final decision.

This transforms your AI from a search engine into a campaign manager, building a cohesive narrative that moves the prospect closer to a “yes.”

Using AI to Repurpose Highspot Content

Your Highspot library is a goldmine, but much of its value is locked away in long-form assets. A 10-page case study is powerful, but it rarely gets read in its entirety over email. A 30-minute webinar recording is insightful, but its key takeaways are buried. The most efficient teams don’t just create new content; they repurpose what they already have.

AI is the ultimate content multiplier. It can instantly distill your densest assets into bite-sized, context-specific nuggets that are perfect for social selling, quick follow-ups, or internal champion enablement.

Your Prompting Framework: “Here is the text from our case study in Highspot: [Paste the text of the case study]. I need to repurpose this for a direct follow-up with a [Prospect Title] in the [Industry] industry. Please provide:

1. Three compelling bullet points highlighting the key results, optimized for a LinkedIn message.
2. A provocative question I can ask the prospect to get them thinking about their own similar challenges.
3. A one-sentence summary for a Slack message to my internal champion.”

The Golden Nugget: The most powerful repurposing is for your internal champion. Use this same technique to create a “Champion Enablement Kit” for any key asset. Ask the AI: “Turn this whitepaper into a one-paragraph executive summary for my champion to forward to their CRO, and generate three talking points they can use to defend this project in an internal meeting.” You’re not just selling to the prospect; you’re arming your internal advocate to sell for you.

Generating “Missing” Content Briefs

The most advanced use of AI isn’t just to work with the content you have, but to identify the content you need. Your sales team is on the front lines, hearing objections and questions every day. Your content library, no matter how robust, will always have gaps. The challenge is turning those anecdotal conversations into a concrete content strategy.

Instead of waiting for quarterly reviews to identify gaps, you can use AI as a strategic content consultant to proactively find and define them.

Your Prompting Framework: “You are a content strategist analyzing our sales enablement library. Based on the common pain points for [Industry] buyers in the [Deal Stage] stage, what type of content is currently missing that would be most valuable for our sales team? Please provide three specific content briefs. For each brief, include a working title, the target persona, the primary question it answers for the prospect, and the ideal format (e.g., 2-minute video, one-page checklist, interactive ROI calculator).”

Why This is a Game-Changer: This prompt moves beyond simple content requests. It forces the AI to think holistically about the buyer’s journey and identify true gaps. It might reveal that you have plenty of top-of-funnel articles for the Awareness stage but are missing a “Total Cost of Ownership” calculator for the Decision stage. Or that you have case studies for enterprise clients but nothing for the mid-market segment your team is now targeting.

By using this prompt monthly, you transform your content planning from a reactive, guesswork-driven process into a data-informed strategy. You stop creating content for the sake of it and start building the exact assets your team needs to overcome the most common barriers to closing deals.

Conclusion: Transforming Sales Conversations with AI-Powered Content

The shift from generic content blasts to hyper-personalized, context-aware communication is no longer a future-state dream; it’s the immediate competitive advantage. By integrating AI-driven prompts with your Highspot library, you’ve seen how to systematically dismantle the most common sales roadblocks. The core benefits are tangible and directly impact your bottom line: you accelerate sales velocity by delivering the right asset at the perfect moment, boost engagement rates by speaking directly to a prospect’s specific pain points, and instill a profound sense of confidence in your reps. They’re no longer just searching for content; they’re executing a precise, data-informed strategy for every single deal.

The Future of AI in Sales Enablement: Predictive, Not Just Reactive

Looking ahead, the role of AI in sales enablement will evolve from a powerful recommendation engine to a truly predictive partner. We’re moving toward a reality where this technology won’t just wait for a prompt. It will integrate directly into your CRM and email workflows, analyzing live conversation data to suggest content in real-time. Imagine an AI that listens to a discovery call, identifies a key objection around security, and instantly surfaces the most relevant compliance guide for your rep to send. The line between sales execution and content strategy will blur, creating a seamless, intelligent loop that anticipates needs before they’re even voiced.

Your First Actionable Step: Prove the Power Yourself

Reading about a new process is one thing; experiencing the efficiency gain is another. The most powerful validation comes from a simple, hands-on test. Your very next step should be to take the master prompt from this guide, adapt it for your most pressing upcoming prospect, and run it through your AI tool. Paste the results directly into Highspot and see what it recommends. Don’t just take our word for it—witness the difference for yourself. You’ll quickly find that arming your team with this capability is the single most impactful change you can make to your sales enablement strategy this year.

Expert Insight

Frequently Asked Questions

Q: How do AI prompts improve content retrieval in Highspot

AI prompts analyze deal context like industry and stage to filter the library, surfacing only the most relevant assets to prevent content paralysis

Q: What is the biggest mistake in sales content sharing

Sending generic assets that don’t match the prospect’s specific industry or buying stage, which damages credibility

Q: Do I need to be a prompt engineer to use this

No, the prompts provided are simple, copy-paste templates designed for immediate use by sales reps