Tips for Modernizing Sales Enablement

“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

They had the tools. They had the team.  They still flatlined. I just helped a client who had: ✅ An expensive tech stack ✅ A high-performing sales team ✅ And stagnant growth. 🚫 They weren’t short on tools. 🚫 They weren’t short on talent. 🚫 They weren’t even short on leads. 🚰 But their funnel? Full of holes. So we mapped it out, leak by leak. And what we found changed everything. By the time we plugged just 12 of the biggest issues, they tripled their qualified pipeline in under 90 days. 💡 12 revenue killing funnel leaks (+ how to fix them): 1. Unclear ICP → Use real behavioral & firmographic data, not assumptions 2. Generic Messaging → Align with lifecycle stages & actual pain points 3. Poor Lead Qualification → Implement BANT/MEDDIC frameworks 4. Sales-Marketing Misalignment → Create SLAs & defined handoff processes 5. Slow Follow-Up → Automate quick replies with personalized templates 6. Complex Lead Forms → Simplify & optimize for mobile conversion 7. Weak Lead Nurturing → Build targeted nurture tracks by segment 8. Missing Sales Enablement → Equip teams with case studies & ROI tools 9. Ignored Middle-Funnel → Deploy webinars & deep-dive content 10. Bad Data Hygiene → Clean CRM data & automate enrichment 11. Low Trust Signals → Strategically place social proof throughout 12. Poor Client Handoff → Start onboarding pre-sale 🔧 The fix doesn't need months or massive budgets. Just clarity, alignment, and execution. Which one is the most important to fix? _____________ ♻️ Repost to help others + Follow Jennelle McGrath for marketing and sales insights

Want the ultimate onboarding and enablement hack? (and no you won't have to comment to get it) It is by far the best way to get up to speed quickly if you're short on time, resources, enablement, etc. Customer Interviews. These are just so incredibly under utilized it's sad honestly. Got get on the phone/zoom with 30-40 customers. (Even better if you can split it by persona, so say like an end user and a decision maker) Then you're going to ask them the 6 'Golden' Questions 1. Why did you buy? - We think we know why people buy thngs, it's time to ACTUALLY know - This will help you craft value props. 2. What problem were you hoping to solve - This is KEY, and notice what PROBLEM, not problems. I want to know the most top of mind problem. This is where I'm building my problem based language and questions from. 3. What were you afraid of before buying - This is where you find out the unspoken objections. They don't tell you everything in the buying process. 4. Whats your favorite part of the product and why - this is where I'm learning what to highlight in my OB and IB messaging, and demo flows. 5. What's changed the most since you got the prodcut? - This is where I'm getting micro testimonials and 'before and after' lanaguge. 6. How would you describe what we do to another _____ (Persona) - this is where we find the comparison language that people understand better. 'Oh you're alot like ______ but you ______ - this is gold. IF YOU DO NOTHING ELSE THIS QUARTER - DO THIS! If you're a solo founder - Do this. If you're a new VP - Do this. If you're a new REP - ASK TO DO THIS. The record them. You now have an absolute gold mine for enablement and onboarding. I recently moved one of my managers from one product to a different product (that's another fun story. leaders are leaders, you can learn a new product) His first assignment? Customer Interviews. Once they are all done, we now also have a full library for new reps to go through as well. UNSPOKEN OBJECTION - But KD how do you get customers to say yes to this? You call them, you tell them you're trying to learn the industry better, you have 6 queastions, would it be ok to ask them? - That's it. No incentives or bribes. Just set up quick calls. UNSPOKEN OBJECTION - I don't have time for this! - If you don't have time for this then I know you don't have time to train your people so you BETTER make time for this. UNSPOKEN OBJECTION - What if I don't have 20 customers yet? - Then you better interview the ones you DO have and then load up on prospect interviews. I'll cover that in another post. Get to interviewing ya'll.

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

There was a debate last week on LinkedIn about the future of Sales Enablement and its corresponding tools in 2025. Here are my 2 cents based on what I’m seeing in the field: 1/ Sales enablement will remain critical, but ownership will shift to managers, SEs, and Product. The enablement function itself isn’t going away—plenty of enablement teams are providing immense value to their organizations. However, their focus is shifting. Instead of direct enablement, they’re equipping managers for coaching, leveraging SEs and PMs for product enablement, and identifying sales problems to solve. This may result in smaller, more focused enablement teams, but it will turn enablement into a collaborative, extended-team effort. 2/ Dedicated sales enablement tools will soon disappear. We’re seeing this firsthand at WorkRamp. Back in 2018–2021, prospects would come to us looking for standalone “sales LMS” solutions. That almost never happens anymore. Customers now want this functionality as an add-on to their LMS, CMS, or revenue platform (like Gong). IMO, the tipping point was Salesforce's acquisition of LevelJump in 2021, marking the beginning of the end for standalone sales enablement tools. 3/ The best way to prove value is through manager and rep validation—not “managing up.” There’s a lot of emphasis on enablement teams “managing up,” like sending weekly CRO reports or monthly activity round-ups. While useful, these aren’t what CROs and CEOs value most. What they really remember is hearing managers vouch for enablement teams or top reps shouting out the enablement team for a deal win. Validation from the field will always outweigh efforts to manage up when it comes to proving the value of sales enablement. If no one’s talking about you, that’s a sign in itself. The entire sales playbook of the last decade is evolving before our eyes, and sales enablement is not immune. That said, I’m bullish that the best enablement teams will emerge even stronger on the other side!

I don't like when sales enablement & sales managers complain that reps don't use the stuff they create. "Reps don't use the new messaging." "Reps aren't following the steps we outlined for them." "Reps keep reverting back to what they were doing before." Boo freakin' hoo. Look in the mirror. 99% of reps want to succeed. They want to do well at their job. They want to make more money. If they thought your stuff would help them do it, they'd use it. Here's why reps aren't using your stuff & how to fix it. ⛔️ You don't involve reps in the creation of the training content Most training content & messaging is created in a silo. An exec who decides to take on a project. The marketing team. Or a pod of enablement managers. The big piece missing? The reps. If you have more than 10 reps, there are reps on the team modeling what good looks like. Those are your champions. Co-create the content with their input. Help them help you get the team excited about what you're creating. And give them credit. ⛔️ You steal the show Most enablement teams have little sales background. Or haven't sold or outbounded in nearly a decade. Imagine learning to cold call from someone who hasn't made a cold call in 5 years. BUT they are experts in process, documentation, and facilitation. Something that, frankly, reps & sales leaders suck at. The best sales enablement teams aren't the stars of skill sessions. They highlight and feature the best reps (and outside experts). ⛔️ You mistake knowing for doing Playbooks are great. But it's only one part of the equation. You need soft skills training, coaching, and reinforcement around REAL scenarios. This means that surveys shouldn't be the primary tool for measuring competence. Run practice sessions with reps. Help them get better at executing the tactics. ⛔️ You don't make it easy enough to implement This one is big. I call it "eating complexity." If you can remove a step for the rep, do it. Every. Single. One. Let's say you're rolling out new persona-based messaging. You need to translate that into talk tracks and email copy. Your enablement should get reps 80%+ of the way there. ~~~ If reps aren't using the stuff you want them to, take ownership. And execute the steps above. My very best clients at companies like Shopify, Gong, Rippling, Zoom, and more do this at a world-class level. Agree or disagree?

Still hiring “hunters” and “farmers”? That’s your first red flag. In today’s B2B buying environment, the old sales archetypes are broken. “Hunters” chase activity. “Farmers” nurture accounts. Neither are equipped to navigate the complex, consensus-driven, executive-led buying process that defines modern B2B sales. And it shows: Win rates are down. (Corporate Visions) Deal cycles are lengthening. (Forrester) C-suite buyers are avoiding sales interactions altogether. (Gartner) Here’s what Gartner says: “The typical buying group has 6–10 stakeholders, each armed with 4–5 pieces of information—and a limited capacity for risk.” And yet… sales orgs are still hiring based on activity volume and pipeline coverage, not strategic influence. At Lucrum Partners, we help organizations reengineer these roles. Why? Because effective sellers today aren’t hunters or farmers. They’re: > Insight Orchestrators Fluent in industry challenges, decision science, and executive priorities. > Business Advisors Trained to create contrast, lead with unconsidered needs, and make the cost of inaction clear. >Revenue Architects Able to map outcomes to financial metrics that resonate with CFOs and CxOs. Why invest in Executive Selling Enablement? Because high-value deals don’t happen at the mid-level. They’re shaped through strategic conversations at the top of the org chart—by people trained to lead them. Stop hiring for yesterday’s job. Start building the team that can win tomorrow’s deals. Institute for Effective Professional Selling (formerly IES) LEMONAID

A sales director just told me: "My rep has a champion who loves our solution and wants to move forward!" I asked him two questions that changed everything… "What's your champion going to tell the CFO when they ask for detailed ROI calculations?" Silence. "How will they handle it when the CEO pushes back and says 'let's stick with our current vendor'?" More silence. This is the problem with 90% of sales teams today. Your reps think that having an enthusiastic champion means the deal is locked up. → But enthusiasm without enablement is useless. Here's what most sales leaders don't realize: Your champion will face internal battles your reps will never see. They'll be questioned by stakeholders your team will never meet. They'll be challenged on details your reps will never hear about. If you don't prepare them for this, they'll fail and your deals die with them. What winning sales teams do differently: 1️⃣Create champion enablement playbooks. One page business cases, ROI calculators, implementation timelines 2️⃣Provide objection handling scripts Arm champions for predictable pushback from finance, procurement, and IT 3️⃣Give competitive differentiation points Help them defend against "cheaper alternatives" 4️⃣Practice internal presentations Role-play the pitch they'll give to their executives What will end up happening? Champions who can actually sell for you, not just cheer for you. Stop assuming that a champion who likes your solution can automatically sell it internally. Start treating champion enablement like the critical sales methodology it is. Your win rates depend on it. — Want the exact system high performing sales teams use to hit quota consistent? Go here: https://lnkd.in/gFj3PUBj

Enablement is in trouble. Trainings are a waste of time. Reps don’t want them or pay attention. So how do you actually teach reps? 1. Think past the training sessions. Better have a comprehensive program which includes post-launch reinforcement. Lunch and learns as well as team-based Q&As help. 2. Set better exec expections. Your c-suite probably doesn’t understand it takes more than a training quiz to learn something or experiment with something new. Make sure they know what your effort will result in, e.g. a minimal amount of effort (i.e. a 1 hr training) will not increase conversion. 3. Define a stopping point. Trainings can go on forever or are too short. Where do you want to land? How long will it take to get there.” Without a destination, the journey sucks. 4. Develop a framework. I have a 3x3 matrix which shows the type of program I need enablement to build based on the cognitive load of change as well as the level of competence needed (see point #2). This makes it easy to know what my team needs. 5. Programs. One-off stuff gets ignored by reps. You need training, quizzes, post-launch training, “study groups,” notes, etc. Teach like a teacher. 6. Culture of learning and reps owning their own development. Until reps understand their responsibility in the process, they’ll never really engage.