Sales Enablement That Actually Enables Sales: A PMM's Playbook

The PMM spent three weeks building the perfect battle card.

Color-coded. Comprehensive. Fourteen pages of competitive intel, product differentiators, and objection-handling scripts. She uploaded it to the sales portal, sent a Slack announcement, and ran a 45-minute training session.

Six months later, she checked the analytics.

Four downloads. Two of them were her own.

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If you work in product marketing, you've lived some version of this story. You've built content that should be useful — content that is useful — and watched it disappear into a folder no rep opens. You've felt the frustration of knowing your competitive positioning is solid and watching the sales team still lose deals to a competitor they could beat with the right answer.

The problem isn't the content. It's the system.

Most sales enablement is built for the person who creates it, not the person who uses it. It's built at a desk, in a meeting room, informed by product specs and analyst reports — not by what actually happens in a live discovery call when a prospect says, "We're also talking to [Competitor]."

This post is about fixing that.

Why Sales Enablement Fails (The Real Reasons)

Before we talk about what works, let's be specific about what doesn't.

1. Content built for awareness, not for the moment of need

Most battle cards are structured like competitive analyses: company background, funding, product features, our strengths, their weaknesses. That's useful context. It's terrible sales ammunition. A rep in a live deal doesn't need background — they need an answer. "Here's what to say in the next 90 seconds."

Sales enablement built for awareness is what you create when you're writing it for yourself. Enablement built for the moment of need is what you create when you've been on those calls.

2. No feedback loop

PMMs create content. Sales uses (or ignores) it. PMMs create more content. Repeat.

Without a feedback loop — a mechanism that tells you which content is being used, which objections it handled, and whether it worked — you're optimizing in the dark. The best enablement programs treat sales as a co-creator, not a recipient.

3. Too much content, too little findability

The average B2B company has 19 separate places where sales assets live. Sharepoint folders, Google Drives, Confluence wikis, Guru cards, and the portal that someone built in 2023 and nobody updated. Reps don't search for content mid-deal. They wing it or ask a colleague.

If your best content takes more than 30 seconds to find, it doesn't exist.

4. Stale, fast

A competitor launches a new feature. A prospect mentions a new objection. Your pricing changes. Your enablement content is now wrong — and nobody knows it.

Content that isn't maintained becomes a liability. A rep who quotes outdated information in a deal is worse off than a rep who said nothing.

5. Measured by output, not outcome

"We published 12 battle cards and 3 decks this quarter" is not a sales enablement success metric. Win rate is. Deal velocity is. Stage conversion is. If your enablement function isn't tracking the metrics that sales tracks, you're measuring effort, not impact.

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The PMM's Sales Enablement Playbook

Here's the framework that actually works — built around how reps sell, not how PMMs think.

Step 1: Map the Real Deal Flow

Before you build anything, go on sales calls. Not to observe the product demo. To observe the conversation.

Specifically, you want to understand:

• What questions do prospects ask most often in discovery?
• When do deals stall, and what's the stated reason?
• Which competitors come up most frequently, and what do prospects say about them?
• What's the objection that killed the last five lost deals?
• What does a rep say when a prospect asks "why you instead of [Competitor]?"

This is your raw material. Everything you build should map to one of these moments.

Target: 10 ride-alongs, 5 lost-deal debriefs, and one afternoon with your best-performing rep before you write a word of enablement content.

Step 2: Build Content for the Moment of Need

The test for every piece of enablement content: When exactly will a rep use this?

If the answer is "when they're preparing for a call," build a one-pager. If the answer is "in the middle of a conversation," build something scannable in 30 seconds or less. If the answer is "after a loss to understand what happened," build a debrief template.

The formats that consistently work:

The One-Page Positioning Cheat Sheet Your single most important enablement asset. One page. Three columns: what we do, who it's for, why it's different from [top two competitors]. Use language from real buyer conversations, not your internal messaging docs. Update it every quarter.

Competitive Battle Cards (Done Right) One page per competitor. Maximum. Structure:

• Quick context (2-3 sentences on who they are and where they play)
• When they come up (at what deal stage and what the prospect usually says)
• What to say (exact language — not talking points, actual sentences)
• What not to say (landmines to avoid)
• Questions to reframe (questions that shift the conversation back to your strengths)

The failure mode is comprehensiveness. A rep mid-deal needs four bullets, not fourteen pages.

The Objection Library A living document of the top 15 objections your reps face, organized by deal stage. For each objection:

• The objection as prospects actually say it
• What's underneath it (the real fear or concern)
• The reframe
• Proof point or customer story to anchor it

This is the highest-ROI thing most PMMs never build.

The Deal Stage Deck Most companies have one pitch deck. Top-performing sales orgs have a different set of assets for each stage: something for first discovery, something for technical evaluation, something for the business case conversation, something for legal and procurement.

Start with the most common bottleneck stage. Where do deals stall most often? Build for that.

Customer Evidence Cards Case studies are for websites. Evidence cards are for deals. One paragraph per customer story: the problem, the measurable outcome, the industry and company size. Organized by vertical and use case so a rep can grab the right story for the right prospect in under a minute.

Step 3: Make It Findable in 30 Seconds

Pick one place. One. Then defend that choice religiously.

The best-performing enablement teams operate with a single source of truth — a Notion workspace, a Guru card library, a pinned Slack channel, a shared Google Drive folder with strict naming conventions. The format matters less than the discipline. A rep who knows exactly where to look will find the content. A rep who has to search across five systems won't look at all.

Name your files the way reps search for them: Competitive - [Competitor Name] - Battle Card.pdf, not Q3 Competitive Intel v7 Final_FINAL.pptx.

Build your structure around deal stages, not content types. Reps think in "I'm in discovery" or "I'm closing," not "I need marketing content."

Step 4: Close the Feedback Loop

Build a feedback mechanism into every major content asset.

The simplest version: a single Slack channel called #sales-enablement-feedback where reps can drop a note when they use something (or when they needed something that didn't exist). Check it weekly. Respond to it. Nothing kills feedback culture faster than hearing nothing back.

More sophisticated: a quarterly win/loss review where you pull 10-15 deals (mix of wins, losses, and stalls) and analyze which enablement content was used, what objections weren't covered, and what competitors weren't in the battle card. (For more on win/loss methodology, see Win/Loss Analysis: The PMM's Most Underused Revenue Weapon.)

The feedback loop should directly inform a quarterly refresh cycle. Every quarter: review top 5 battle cards against actual deal data. Archive what's not being used. Update what's stale. Build what's missing.

Step 5: Measure What Sales Measures

Stop measuring content volume. Start measuring deal outcomes.

The metrics that matter:

• Win rate overall and win rate by competitor — is your competitive enablement improving outcomes?
• Stage conversion rate — does enablement content help more deals move from evaluation to business case?
• Deal velocity — are reps closing faster when they use the positioning cheat sheet vs. when they don't?
• Enablement adoption rate — what % of reps use your content at least once per deal cycle?

The last metric is your early warning system. If adoption is low, the problem is findability, relevance, or format — not the quality of your analysis. Fix the format before you assume nobody cares.

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The PMM's Relationship with Sales: What Makes or Breaks Enablement

The best sales enablement programs I've seen share one non-obvious trait: PMMs and sales reps have a real relationship. Not a monthly stakeholder update. An actual relationship.

That means PMMs have a handful of sales champions — high-performing reps who will test new content, give honest feedback, and tell you when something is wrong before it's wrong in a hundred deals. It means PMMs sometimes join calls — not to present, but to listen. It means PMMs are in the #deal-desk Slack channel and see what's actually happening.

This isn't about being liked. It's about staying calibrated. The product roadmap changes. The competitive landscape shifts. Buyer psychology evolves. Your enablement content needs to evolve with it — and the only way to know when is to stay close to the deals.

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Where to Start: The 30-Day Quick-Start

If you're building sales enablement from scratch, here's the sequence:

Week 1: Research only. No building. Ride along on five calls, review ten lost-deal notes, interview three top reps. Document every objection, competitor mention, and sticking point you hear.

Week 2: Build the positioning cheat sheet. One page. Shared in Slack. Ask three reps if it matches how they actually talk about the product. Revise based on their feedback.

Week 3: Build the top two battle cards. Prioritize the competitors that come up most in lost deals, not the ones marketing worries about most. (These are often different.) Competitive intelligence research should inform this, but reps should validate it.

Week 4: Build the objection library. Start with the 10 most common objections from your Week 1 research. Map each one with: the objection as stated, the underlying concern, the reframe, and the proof point.

After 30 days: review adoption. What's being used? What isn't? What did reps ask for that you haven't built yet? Let the answers drive the next 30 days.

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The Bigger Picture: Sales Enablement as Positioning Feedback

Here's the shift that changes how PMMs think about their role:

Sales enablement isn't just a service you provide to sales. It's a positioning feedback mechanism.

Every objection is a positioning gap. Every "why not you?" is a differentiator you haven't communicated clearly enough. Every "we went with [Competitor]" is market intelligence.

When you treat enablement as a two-way system — not just content going to sales, but signal coming back — you get something more valuable than a better battle card. You get a real-time window into how your positioning is landing in the market.

That signal should flow into your messaging work, your positioning framework, your pricing and packaging decisions, and your GTM strategy. Sales enablement done right doesn't just support sales. It improves your entire go-to-market.

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