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AI Enablement June 12, 2025

In theory, enablement content should be one of the highest-leverage assets inside any go-to-market system.

Sales decks, battlecards, one-pagers, product briefs, objection handling guides, customer stories — these are supposed to equip revenue teams with everything they need to drive conversations forward.

But in practice? Roughly 80% of marketing enablement content never gets used.

Sales doesn’t touch it. Customer success can’t find it. Marketing teams churn out asset after asset that sits in Google Drive folders or enablement platforms collecting digital dust.

The question is: why?

The answer isn’t complicated — but it is uncomfortable.

Your enablement content isn’t aligned to how deals actually happen.

The Disconnect Between Content and Conversation

Most marketing enablement content gets built in a vacuum:

  • It’s organized around product features, not customer outcomes.
  • It’s written for internal launches, not real customer objections.
  • It’s built around idealized buyer journeys, not the messy reality of pipeline friction.

The result? Content that sounds great in theory, but feels irrelevant in the heat of live sales conversations.

Reps need assets that speak to where the customer is in this deal — not where marketing thinks they should be in some generic funnel.

Where Enablement Content Breaks Down

Let’s make this even more concrete.

1. Content Built on Product Narratives, Not Deal Narratives

Example:
Marketing creates a beautifully designed 20-slide deck walking through every product capability and value prop.
Sales rep opens the meeting. The customer says: “We’re struggling with data governance across three business units.”

Now the rep is left trying to retrofit the marketing deck into a conversation about organizational complexity and data stewardship — but the deck was never built to support that.

The rep abandons the deck entirely.

2. Content That Ignores Pipeline Friction Points

Example:
Marketing publishes a case study highlighting a customer win after full deployment.
The prospect is stuck trying to justify upfront implementation costs.
The content doesn’t help neutralize the cost objection, so the rep improvises.

Result: The rep never sends the case study. Another piece of unused content.

3. Content That’s Static While Deals Are Dynamic

Example:
Marketing produces quarterly battlecards with canned competitive messaging.
Meanwhile, the competitor just rolled out a new feature that is dominating the conversation on recent deals.
The rep is left scrambling for up-to-date talking points.

Static content falls behind. Real deals don’t wait for quarterly updates.

The Fix: Build Enablement From Actual Deal Intelligence

The solution isn’t to build more content.
The solution is to build situational content — directly informed by live deal data.

Here’s how high-performing teams do it:

Step 1: Use Deal Intelligence to Map Real Buying Behavior

Instead of guessing at what assets are needed, analyze your actual sales conversations:

  • Discovery calls
  • Loss reasons
  • Objection patterns
  • Deal stage conversion rates
  • Win/loss interviews

Look for patterns in where deals slow down, stall, or fall apart. That’s where you target your enablement content.

Example:
If 60% of late-stage deals are derailed over security concerns, don’t build another feature guide — build a dynamic security objection handling guide that arms reps with customer-proven answers.

Step 2: Build Micro-Content for Pipeline Friction Points

Most reps don’t need 30-slide decks. They need quick, modular assets they can deploy in the moment based on what’s happening in the deal.

  • One-pagers for specific objections
  • Competitive response snippets
  • Pricing and value comparison tables
  • Customer stories mapped to similar buying scenarios
  • Short videos or slides that reframe a blocker

Example:
Instead of one generic case study, create short customer vignettes for vertical-specific wins: “How Company X Cut Vendor Risk by 32% in Under 90 Days.”

Now reps have ammunition that speaks directly to the customer’s world.

Step 3: Use AI to Dynamically Map Objections and Generate Battlecards

Here’s where modern AI changes the enablement game entirely.

AI-powered systems can analyze call recordings, email threads, and CRM notes to surface emerging objection patterns across deals.

Instead of waiting for quarterly enablement updates, AI can:

  • Flag new competitor moves based on live customer conversations.
  • Generate battlecard updates dynamically as new objections surface.
  • Create tailored talking points that match the specific customer’s context.

Example:
Your reps are seeing a surge in “we’re already using XYZ vendor” objections.
AI flags the trend, automatically generates a refreshed competitive grid, and pushes it directly to reps working those deals — all within days, not quarters.

Step 4: Train Reps on How Customers Actually Buy

Finally, enablement isn’t just about content. It’s about rewiring how your reps approach conversations.

Too often, reps are trained on “what we sell” — feature lists, product specs, demo flows. But top-performing reps master “how customers buy” — the internal debates, risks, and tradeoffs prospects navigate to reach a decision.

Great enablement includes:

  • Buyer behavior playbooks
  • Internal stakeholder mapping guides
  • Value communication frameworks tied to business outcomes
  • Coaching on navigating the customer’s buying committee

Example:
If your customers routinely involve CFOs late in the deal, create CFO-specific business case templates your reps can use to help champions sell internally.


The Samesum Framework: Enablement Tied to Revenue Reality

At Samesum, we see enablement as a living system, not a one-time content dump.

Our framework helps companies:

  • Map enablement directly to real pipeline friction
  • Build modular, situational micro-content that reps can actually use
  • Deploy AI-driven objection monitoring and battlecard generation
  • Train revenue teams on buying behavior, not just product specs

The result? Content that’s used. Objections that are neutralized. Pipeline that moves.

If your enablement content feels invisible, stale, or disconnected from revenue — let’s fix that.

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