I spent three months building the perfect sales enablement program. Comprehensive training deck, detailed battlecards, competitive positioning, objection handling scripts, demo videos, case studies—everything sales could possibly need.
I delivered a two-hour training session. Sales loved it. They said: "This is exactly what we needed."
Two weeks later, I sat in on sales calls. Nobody was using any of it.
They weren't using the positioning. They weren't using the battlecards. They weren't handling objections the way we'd trained. They'd reverted to their old pitch within days.
I asked a rep: "Why aren't you using the new positioning?"
He said: "I don't remember it. Can you send me the deck again?"
That's when I learned enablement isn't about creating training materials. It's about building systems that make training stick.
The Readiness box in Pragmatic Framework—sales tools, training, and support—is the last column for a reason. You can't enable sales until you've done the Market work (understand buyers), Focus work (positioning), Business work (pricing), and Programs work (launches).
But most PMMs treat Readiness as "make sales decks." They create beautiful materials, deliver training, and wonder why nothing changes.
Real enablement changes behavior. If your win rate doesn't improve after enablement, you didn't enable—you just created documents.
What the Readiness Box Actually Means
Pragmatic's Readiness box includes sales tools (decks, battlecards, scripts), sales training, and sales support.
Most PMMs focus on tools—create a deck, make a battlecard, write some objection handlers. They think: "If I give sales the right materials, they'll use them."
They won't. Sales uses what's memorable, accessible, and reinforced—not what's comprehensive.
I learned this after my fourth failed enablement program. Each time, I'd built better materials. Each time, adoption was terrible.
Then I realized: Enablement isn't about giving sales information. It's about changing what they say and do in conversations.
Building Sales Tools That Actually Get Used
Most sales tools fail because PMMs optimize for comprehensiveness, not usability.
You create a 60-slide pitch deck covering every feature, every use case, every persona. You build battlecards with 12 competitive differentiators. You write objection handlers for 30 different objections.
Sales looks at this and thinks: "I don't know where to start."
I learned to build tools optimized for the moment of use instead.
I used to build comprehensive pitch decks: company overview, product capabilities, customer stories, technical architecture, pricing, next steps.
Sales would use slides 1-5 and ignore the rest.
I started building modular decks organized by conversation type instead. For discovery conversations, I built a 15-slide deck that started with who we are and what we do in 30 seconds, then covered the top 3 market problems we solve with customer evidence, showed how we're different from what they're using today, and ended with discovery questions to qualify fit.
For demo conversations, I built a 20-slide deck that recapped their discovery (their problems, our fit), walked through product organized by their workflow instead of our features, showed an ROI framework based on their numbers, and ended with customer proof points from similar companies with similar results.
For business case conversations, I built a 12-slide deck that quantified the problem (cost of status quo), showed solution value (how we reduce that cost), modeled ROI with their numbers and conservative assumptions, and addressed risk mitigation around implementation, adoption, and vendor concerns.
Each deck was designed for a specific conversation. Sales didn't need to edit or customize—they could grab the right deck and use it.
Adoption went from 30% to 85%. Not because the content was better—because it was easier to use in real conversations.
I did the same thing with battlecards. I used to build comprehensive battlecards: competitor overview, feature comparison matrix, 12 differentiators, objection handlers, customer wins, pricing comparison.
Sales never used them. Too much information to digest in the 10 seconds before a competitive question comes up.
I started building one-page battlecards organized by conversation flow instead. For each competitor, I explained when they come up—prospects mention them in this specific situation, they're strong in this segment or use case but weak in our sweet spot. I gave sales a 30-second positioning statement: they're a great choice if you're their ideal customer, we're built for our ideal customer, the main difference is this one or two sentence differentiation.
I listed the top 3 differentiators with what to emphasize. We do X and they don't, this matters because of this business impact. Our approach to Y is this specific difference, customers choose us when this use case applies. We're this measurable difference, which means this customer outcome.
I showed how to handle "They have this feature and you don't" objections. True, they have that feature. What we've found is this customer insight about why that feature matters less than our approach. Can I show you how we solve the underlying problem differently?
I included proof points with customer evidence. This company chose us over them because of this specific reason. This company switched from them to us and saw this specific outcome.
I even told sales when they'll lose. If the prospect needs this specific capability we don't have or they're in this segment we're not built for, the competitor might be a better fit. Qualify for these criteria before competing.
One page. Conversation-ready. Sales can reference it in 30 seconds during a call.
Battlecard usage went from "nobody uses them" to "every competitive deal references them."
Making Training Stick Through Repetition
Most sales training fails because PMMs deliver it once and assume it sticks.
You run a 90-minute training session, share the recording, and expect sales to remember everything from positioning to objection handling to competitive differentiation.
Two weeks later, they remember nothing.
The problem is that information dumps don't create behavior change. Repetition and reinforcement do.
I don't do training sessions anymore. I do enablement programs.
In week one, I run a core training as a live session. Sixty minutes covering positioning, target customer, and top 3 differentiators. Thirty minutes for Q&A and role-play. Homework: record a 2-minute pitch using the new positioning.
In week two, I send reinforcement async with office hours. I send a short recap video (5 minutes) of core positioning. I send the most common question from week 1 answered. I offer 30-minute office hours for questions. I review homework pitches and give feedback.
In week three, I do a deep dive as another live session. Thirty minutes on competitive positioning and battlecard walkthrough. Thirty minutes role-playing handling top 3 objections. Homework: use battlecard in a real competitive deal and report back.
In week four, I send more reinforcement async with a case study. I send a competitive win breakdown showing how a rep used the positioning to beat a competitor. I send an updated battlecard based on week 3 feedback. I collect questions and objections that came up in real deals.
Ongoing, I do weekly reinforcement. Monday: "Quick Win" email with one tactical tip (2-minute read). Thursday: "Deal Breakdown" analyzing a recent win or loss (3-minute read). Monthly: live office hours for Q&A and deal reviews.
The difference is that information is delivered in small doses over time, reinforced through repetition, and applied to real deals.
Sales retention went from "I don't remember what we covered" to "I use this in every deal."
Building a Sales Support System That Scales
Most PMMs think enablement ends when training ends.
You deliver the training, share the materials, and move on to the next launch. Sales is on their own to figure out how to apply it.
Then sales asks questions in Slack, in random meetings, in one-off emails. You answer the same questions five times. Nobody benefits from the answers because they're scattered across channels.
I built a centralized sales support system instead.
I created a Notion workspace (could be Confluence, Google Sites, whatever) organized by the questions sales actually asks.
When they ask "How do I pitch this?" they find discovery deck for initial conversations, demo deck for product walkthroughs, business case deck for procurement conversations, and quick pitch for 2-minute intros.
When they ask "How do I handle objections?" they find the top 10 objections with responses, pricing objections searchable by specific objection, competitive objections with one page per competitor, and technical objections with links to docs or product.
When they ask "How do I compete against this competitor?" they find a one-page battlecard per competitor, recent competitive wins showing what worked, and qualify-out criteria for when to walk away.
When they ask "What proof points can I use?" they find customer stories organized by industry, use case, and company size, ROI examples with actual customer results and numbers, and customer quotes and testimonials.
When they ask "How do I price and package this?" they find a pricing calculator, discount approval matrix, and package comparison showing when to position which tier.
When they ask "Who do I ask if I'm stuck?" they find PMM office hours schedule, sales engineering coverage, and Slack channel for quick questions.
The rule was simple: every enablement asset, battlecard, and training gets added to the hub. One source of truth, searchable, organized by question type.
Sales could find what they needed in 30 seconds instead of hunting through Slack, email, or shared drives.
Support questions dropped 60% because sales could self-serve answers. The questions I did get were more strategic ("How do I position against this unique situation?") instead of tactical ("Where's the deck?").
Measuring What Actually Matters
Most PMMs measure enablement by activity metrics: training attendance rate, deck downloads, battlecard views.
These metrics tell you if people showed up or clicked. They don't tell you if behavior changed.
I learned to measure outcomes instead.
Short-term (2-4 weeks post-enablement), I measured tool adoption—what percentage of reps were using new positioning in calls, which I could hear in Gong recordings. I measured battlecard usage—what percentage of competitive deals referenced the battlecard. I measured support questions—were reps asking better strategic questions or basic questions showing they didn't retain training?
Medium-term (6-8 weeks post-enablement), I measured discovery quality—what percentage of discovery calls covered positioning and qualification criteria. I measured competitive win rate—did win rate improve in competitive deals? I measured deal velocity—did sales cycle speed up because reps pitched better?
Long-term (3-6 months post-enablement), I measured win rate by rep—which reps adopted new positioning and which didn't, and what was the win rate gap? I measured deal size—did better positioning lead to larger deals or lower discounting? I measured retention—were reps still using the positioning or did they revert?
The test was simple: if I couldn't draw a line from enablement to improved win rates or faster sales cycles, the enablement didn't work.
I reviewed these metrics quarterly with sales leadership and asked: "Did this enablement change outcomes?"
If yes, we did more of it. If no, we figured out what broke (content, delivery, reinforcement) and fixed it.
Learning From Common Enablement Mistakes
After running dozens of enablement programs, I started seeing patterns in what made them fail.
The first mistake was building comprehensive materials instead of usable tools. Teams created 60-slide decks, 5-page battlecards, and 30 objection handlers because they wanted to be thorough. Comprehensive isn't usable. Sales doesn't know where to start or what to use in real conversations. The fix was building modular tools optimized for specific conversation moments. One-page battlecards. Fifteen-slide decks for discovery. Five-minute videos for specific objections.
The second mistake was one-time training instead of ongoing programs. Teams delivered a 90-minute training session, shared the recording, and called it enabled. Information dumps don't stick. Sales forgets 80% of what you covered within two weeks. The fix was building enablement programs with weekly reinforcement over 4 weeks, then ongoing support through quick wins, deal breakdowns, and office hours.
The third mistake was measuring activity instead of outcomes. Teams tracked training attendance, deck downloads, and content views. Activity metrics don't tell you if behavior changed or if win rates improved. The fix was measuring tool adoption (percentage of calls using new positioning), competitive win rates, deal velocity, and retention of enablement content over time.
The fourth mistake was having no centralized enablement hub. Sales asked questions in Slack, email, meetings. You answered the same questions repeatedly. Knowledge was scattered. Sales couldn't find what they needed. You were constantly answering basic questions instead of strategic ones. The fix was building a centralized enablement hub organized by question type. One source of truth, searchable, updated with every new asset.
Why Most Enablement Fails
The uncomfortable truth: Most enablement fails because PMMs optimize for delivering training, not for changing behavior.
You think: "If I give sales the information, they'll use it."
They won't. Because they're busy and won't study your 60-slide deck. Because they forget 80% of what you covered in training within two weeks. Because they revert to what's comfortable (their old pitch) under pressure. Because they can't find your materials when they need them.
What actually changes behavior is different.
Tools that are easy to use in the moment of need. Not five-page competitive analyses—one-page battlecards.
Training delivered in small doses over time with reinforcement. Not 90-minute sessions.
A centralized hub where they can find what they need in 30 seconds. Not scattered across Slack and Google Drive.
Ongoing support through office hours and deal reviews. Not "here's the training, good luck."
I've watched sales teams go from "we don't use PMM materials" to "we use battlecards in every competitive deal" not because I created better content—because I made it easier to use and reinforced it until it stuck.
Where GTM Strategy Becomes Execution
You can have perfect market insights (Market box), brilliant positioning (Focus box), compelling business cases (Business box), and coordinated launches (Programs box).
But if sales can't pitch it, handle objections, and beat competitors, none of that matters.
The Readiness box is where strategy becomes execution. Where positioning becomes pitches. Where differentiation becomes competitive wins.
Most PMMs skip this box or treat it as "create some decks." Then they wonder why win rates don't improve.
I learned to build tools optimized for usability, not comprehensiveness. I delivered training as programs with ongoing reinforcement, not one-time sessions. I created a centralized enablement hub so sales could self-serve. I measured behavior change and win rates, not training attendance.
Then I watched what happened: Sales started using the positioning. Competitive win rates improved. Deal velocity increased.
That's when I knew enablement worked.
I stopped creating materials. I started changing behavior.