How to Maximize Sales Enablement Results

Every enablement team has the same problem: - Reps say they want more training. - You give them a beautiful deck. - They ghost it like someone who matched with Keith on Tinder. These folks don't have a content problem as much as they have a consumption problem. Think of it thusly: if no one’s using the enablement you built, it might as well not exist. Here’s the really scary part: The average org spends $2,000 - $5,000 per rep per year on enablement tools, programs, and L&D support. But fewer than 40% (!!!) of reps consistently complete assigned content OR apply it in live deals. So what happens? - You build more content. - You launch new certifications. - You roll out another LMS. And your top reps ignore it all because they’re already performing, while your bottom reps binge it and still miss quota. 🕺 We partner with some of the best enablement leaders in the game here at Sales Assembly. Here’s how they measure what matters: 1. Time-to-application > Time-to-completion. Completion tells you who checked a box. Application tells you who changed behavior. Track: - Time from training to first recorded usage in a live deal. - % of reps applying new language in Gong clips. - Manager feedback within 2 weeks of rollout. If you can’t prove behavior shift, you didn’t ship enablement. You shipped content. 2. Manager reinforcement rate. Enablement that doesn’t get reinforced dies fast. Track: - % of managers who coach on new concepts within 2 weeks. - # of coaching conversations referencing new frameworks. - Alignment between manager deal inspection and enablement themes. If managers aren’t echoing it, reps won’t remember it. Simple as that. 3. Consumption by role, segment, and performance tier. Your top reps may skip live sessions. Fine. But are your mid-performers leaning in? Slice the data: - By tenure: Is ramp content actually shortening ramp time? - By segment: Are enterprise reps consuming the right frameworks? - By performance: Who’s overconsuming vs. underperforming? Enablement is an efficiency engine...IF you track who’s using the gas. 4. Business impact > Feedback scores. “Helpful” isn’t the goal. “Impactful” is. Track: - Pre/post win rates by topic. - Objection handling improvement over time. - Change in average deal velocity post-rollout. Enablement should move pipeline...not just hearts. 🥹 tl;dr = if you’re not measuring consumption, you’re not doing enablement. You’re just producing marketing collateral for your own team. The best programs aren’t bigger. They’re measured, inspected, and aligned to revenue behavior.

“One of our salespeople keeps going rogue, and I’m doing all I can to reel him in,” shared a seasoned CMO at a tech startup. While the other CMOs in the Huddle offered guidance on gaining alignment, it made me wonder: Is it time to completely rethink Sales Enablement? The problem isn’t just rogue reps. It’s a system that encourages chaos. One CMO shared, “We’ve got great messages that resonate, but Sales Enablement says it’s the wrong time to share them.” Another noted, “Product is producing substandard collateral because Sales went directly to them—cutting Marketing out of the loop entirely.” It’s no wonder CMOs are frustrated. We build slick decks and elegant one-pagers—yet Sales clings to a 2019 slide with the wrong logo. We set up portals, and no one logs in. We host training sessions, and still get last-minute Slack messages: “Hey, do we have a case study for a mid-sized healthcare firm in Ohio?” So what’s a savvy CMO to do? 1. Understand Your Rogues. Before condemning, listen. The rogue rep in question was closing deals—but not the kind you’d want. It turns out he was winning on price, undercutting the value proposition and increasing churn. As one CMO put it, “They don’t talk about our real differentiators—just a three-month discount.” If you don’t know what’s being said on sales calls, you can’t fix the funnel. 2. Collaborate, Don’t Dictate. Rather than fighting every deviation, smart CMOs co-create. One suggestion: “Treat the rogue like a partner, not a problem.” Pull them in. Learn what’s working. Then use that to shape flexible messaging frameworks—ones that adapt to buyers without fracturing the brand. 3. Think Co-Creation, Not Vending Often, the problem isn’t the quality of the materials—it’s the disconnect between what Marketing thinks reps need and what Sales uses. As one CMO admitted, “We created great sell sheets—but one rep told me he never looked at them.” Why? Because they didn’t fit how he sold. Instead of assuming what Sales needs, ask. Sit in on calls. Shadow top performers. Then tailor your materials around real objections, use cases, and buyer personas. 4. Build Smart Systems, Not Static Assets. Sales enablement isn’t about creating more slides—it’s about architecting systems that drive revenue. From AI-powered content recommendations to dynamic digital deal rooms, today’s toolkit can turn random acts of enablement into precision plays. (Need ideas? See link in comments.) 5. Let Sales Be Sales—but Keep Score. Sometimes, the best way to prove the value of your materials is to put on your own sales hat. One CMO noted, “I started running a few calls myself to pressure-test the content.” Another shared, “We gave the events budget to Sales, along with the accountability. That ended the debate quickly.” Bottom line: Sales Enablement in 2025 isn’t about policing rogue reps. It’s about empowering the entire team—Sales included—with tools, insights, and guardrails that elevate performance without squashing initiative.

2025 won’t be about what you add, it will be about what you remove. The winners won't be those who add more complexity. They'll be the ones who master the art of removing friction. But, HOW do we do that for both sides of the revenue equation for buyers and customer facing teams? 1️⃣ 𝗛𝗼𝘄 𝘁𝗼 𝗥𝗲𝗺𝗼𝘃𝗲 𝗕𝘂𝘆𝗲𝗿 𝗙𝗿𝗶𝗰𝘁𝗶𝗼𝗻: • Make information discoverable (think Netflix, not library) • Enable self-service exploration (let them learn their way) • Connect every touchpoint (stop asking them to repeat themselves) • Provide instant answers (or better yet, anticipate questions) • Match their preferred buying motion (not your selling motion) 2️⃣ 𝗛𝗼𝘄 𝘁𝗼 𝗔𝗺𝗽𝗹𝗶𝗳𝘆 Customer facing teams 𝗪𝗶𝗻𝘀: • Bring insights to where they work (not another tab) • Surface what's working (and who it's working for) • Automate the routine (so they focus on relationships) • Make best practices obvious (not buried in playbooks) • Connect client signals to seller actions (right action, right time) 3️⃣ 𝗧𝗵𝗲 𝗦𝘆𝘀𝘁𝗲𝗺𝘀 𝗣𝗹𝗮𝘆: • Connect platforms that should talk • Remove duplicate data entry • Automate the predictable • Surface exceptions that need attention Remember: Every extra click Every delayed response Every disconnected conversation Every scattered resource ...is friction that stands between your buyers and their success (and your teams and their wins). True enablement as a concept, not the team, isn't a function or a department—it's a strategic pillar that does two things masterfully: 1. Eliminates barriers that slow buyers down 2. Amplifies what helps sellers win 𝗧𝗵𝗲 𝗥𝗲𝘀𝘂𝗹𝘁𝘀: • Buyers get clarity instead of complexity • Sellers deliver value instead of managing processes • Teams achieve momentum instead of maintaining systems The future belongs to companies who understand that the best technology doesn't add steps—it removes them. The best strategies don't create new hurdles—they eliminate existing ones. Success in 2025 won't be measured by how much you can add to your tech stack. It will be measured by how much friction you can remove from your revenue engine. The real unlock? AI isn't just another tool—it's the invisible thread that weaves everything together: • Maps and predicts friction before it happens (across every journey) • Amplifies human expertise (instead of replacing it) • Learns from every interaction (what works, what doesn't) • Automates the routine (so humans focus on relationships) • Brings insights to every moment (right context, right time) • Connects signals across systems (no more blind spots) Any and all tech that I advise for, promote, consult, or evangelize for does this. Old tech requires people, (buyers and sellers) to go to the tech. AI/new tech GOES TO THE HUMAN. Tech that works seamlessly in your workflow instead of another tab or step will win. My mantra next year? Remove friction. I’m not the best at it, but Dagnabit, I’m working on it. #Enablement #ai

How I create performance-focused enablement: First, I create a "Model of Performance (MoP)." This consists of: 1. Outputs: what to produce/deliver OTJ (and to what standard) 2. Actions: what tasks to perform to produce the outputs 3. Knowledge / Skills: what topics are needed to perform the actions. This MoP becomes the foundation for any enablement resources. Take a course or training, for example: 1. Output = the course/training 2. Actions = the modules/sections within the course/training 3. Knowledge / skills = the teaching points within the modules/sections This ensures all of the knowledge / skills they learn and practice are IN THE CONTEXT of how they need to apply them on the job (maximizing the chances them actually doing it). Plus, the MoP serves as a guide for other interventions and resources: - Sales Ops now knows how to document the process and what improvements can be made to it or the tools involved. - Front-line managers now have standards to use when inspecting and coaching. - Enablement can continue to create highly relevant and contextual resources like job aids or checklists. --- If you want to become performance-focused, you have to define what performance is. #salesenablement #sales

Your sales enablement team is drowning. Can AI agents help? Just left a fascinating conversation with a sales enablement leader at a Fortune 100 company that left me thinking: we're still solving 2025 problems with 2010 tools. Here's what keeps them up at night: 1) Creating assessments is a manual slog, eating up hours they don't have 2) Reps waste 30% of their time hunting for documents across fragmented systems 3) Training completion data requires constant chasing and manual reporting 4) Roleplays? Great in theory, rarely happen in practice (hello, unprepared customer calls!) 5) The same questions flood their inbox daily, stealing focus from strategic work Sound familiar? The hard truth: while we've evolved how we sell, how we enable sellers remains stuck in the past. But here's where it gets interesting. AI agents aren't just coming - they're already here, quietly solving each of these challenges: ︎︎👉 Auto-generating contextual assessments from existing content 👉 Finding the right document instantly through natural language search 👉 Providing real-time training analytics without the manual work 👉 Offering on-demand roleplay sessions with objective feedback 👉 Creating institutional knowledge hubs that answer repetitive questions The companies adopting these solutions now aren't just saving time - they're fundamentally changing the economics of sales enablement. One rep told me their time-to-productivity dropped from 6 months to 2 months. The question isn't if Agentic AI will transform sales enablement. It's whether you'll be ahead of the curve or playing catch-up. What's the biggest enablement challenge you think AI could solve for your team? #SalesEnablement #AI #SalesTransformation #FutureOfSales