Digital Sales Coaching for Increased ROI

Last quarter, we spent $1,404,619 on AI tokens - an all-time high - and the ROI wasn’t what we expected… Most of the ROI didn’t come from “flashy AI”, it came from boring AI doing boring work at scale. Here’s where our spend went and what actually moved the needle: 1. Telling reps who to call today (and why) We’re using AI to sift through millions of signals and tell reps who to talk to today and why. The signals that we’ve found matter: Job changes (new decision makers = new opportunities), buying committee changes and intent signals (active web research and pricing page visits). The big ROI driver is helping our customers with daily prioritization so they don’t have to go fishing for actionable info. At ZoomInfo, We’ve seen a 25-33% increase in meeting quality and opp creation when AEs are sourcing using our AI tools. Win rates also jump from 16-20% to 30%. 2. Writing outreach that doesn’t sound automated We’re moving from “20 segments of 1,000” to 20,000 segments of 1. Not “VP IT at enterprise insurance” messaging… but John at State Farm, who we talked to last year, who competes with three of our customers, with context pulled in automatically. Customer ROI here ultimately comes from better response rates and higher close rates by being more relevant. Buyers care when you show you care. 3. Turning sales calls into usable data Every sales call (ours and customers) is recorded using @Chorus and becomes structured data: objection patterns, competitor mentions, deal risk, coaching moments. We’ve found the benefits of this are huge - 25-30% faster ramp time for new reps, and 10-15% larger deal sizes through better discovery and value articulation. The average rep sells more like the best rep. 4. Speeding up low-value engineering work Every engineer at Zoominfo has Intellij and VS Code w/ Cline. AI handles the unglamorous stuff: Boilerplate code, refactors, test coverage. We’ve seen ~25–30% faster execution on these routine tasks, which frees senior engineers to focus on system design and real product innovation. Our biggest lesson so far has been that if your data foundation is garbage, AI just helps you move faster in the wrong direction. You won’t get AI “working” until you have contextual customer/prospect data centralized, and you can actually build on top of it. We’re still early and we’re trying a lot of things but these have been the highest ROI drivers by a mile. If you’re testing AI in your GTM stack, drop a comment with what’s actually working for you - I’m all ears.

"Just checking in on that proposal." I sent this email the other day. My 4th "check-in" to this prospect. No response. Frustrated, I called my sales amigo: "I don't get it. Great demo, they loved our solution, but now they've gone dark." He asked a simple question: "What content have they engaged with since your demo?" I had no idea. The truth hit me: I was flying blind. I sent PDFs, presentations, and pricing. But had zero visibility into what they actually viewed. Were they showing it to others? Did they have concerns? Was anything resonating? I had no clue. Last week, I tried a different approach: After a promising demo, instead of attaching files to an email, I created a digital sales room. Inside: - Everything they needed to evaluate us - Organized by their specific priorities - Clear calls-to-action for next steps The difference was immediate: Day 1: The main contact viewed the ROI calculator twice Day 2: They shared it with their CFO (who I'd never spoken to) Day 3: The CFO spent 30 minutes on pricing information Day 4: They downloaded our security documentation Day 5: The main contact viewed implementation timeline 3 times I picked up the phone: "I noticed you've been looking at our implementation process. Any questions about that timeline?" Their response: "How did you know? Yes, actually, we're concerned about..." The objection surfaced BEFORE it killed the deal. Old school selling: Send content. Cross fingers. Guess what's happening. Modern selling: Share content. Watch engagement. Address concerns proactively. The hard truth: 90% of buying happens when you're not in the room. Are you still pretending those blind "check-in" calls are a strategy? Or are you watching how prospects actually consume information when you're not there? Stop asking prospects to update you. Start building systems that show you what's really happening. Agree?

I’ve been running deals with digital sales rooms for 2.5 years. Here are 10 async revenue plays we use that go way beyond the obvious. Most teams still treat DSRs like a nicer Dropbox. Drop a deck. Add a demo. Hope someone shares it internally. That’s not async selling. That’s digital clutter. Here’s what’s really happening: → Buying happens between meetings → Champions pitch when you're not there → And most teams offer zero support when it matters most If your process still relies on live calls and recap emails... You're behind. Because the best teams? They don’t just use DSRs. They turn them into a competitive advantage. Here are 10 async plays we’ve seen drive real revenue impact beyond the obvious: 1. Prep buyers before the demo Share context and proof early so the live call actually moves things forward. 2. Loop in late-stage decision makers Give execs what they need to catch up, no call required. 3. Help buyers compare you internally Share ROI, case studies, and differentiators they can forward to others. 4. Speed up procurement Send legal and security docs early so redlines don’t stall the deal. 5. Follow up after events with real value Send tailored takeaways not just “great to meet you.” 6. Align better with partners Share one clear message when multiple sellers are involved. 7. Replace live reference calls Let buyers hear from happy customers without booking another meeting. 8. Make QBRs and renewals smoother Show results and plans before you even join the call. 9. Support expansion without pressure Share new ideas, use cases, and features they can explore in their own time. 10. Train new reps with real deals Let them learn from what great actually looks like, not just shadowing. We use trumpet 🎺 to run every one of these plays. It’s the DSR platform that makes async selling feel simple for the team and the buyer. DSRs aren’t a nice-to-have follow-up tool. They’re a system to win more deals with less friction. And most teams are barely scratching the surface. Which of these async plays would actually help your team close more deals right now? PS. I bundled these non-obvious use cases into a full async GTM playbook. Subscribe on Substack if you want the full breakdown. It’s free.

💡 I recently changed how we do deal reviews They felt too much like update meetings that never went deep enough. And it reminded me of how many sales teams we train whose managers still do deal reviews in a telling vs. a coaching style. I was guilty of that as well - loosing the opportunity to help reps improve and identify gaps that when filled will drastically increase the chances of winning the deal. Here’s how I run them today: 1️⃣ Opening: Give the rep the stage Rep leads: Presents 1, max 2 deals using our qualification methodology called PIPUD (MEDDIC, SPICED etc. are what you may use). Why: You immediately see whether they understand the key levers and can think structurally. Your role: Listen actively, take notes, don’t jump in. Benefit: You build ownership - the rep “sells” you their deal. 2️⃣ Deepen: Ask questions, don’t make statements Once the rep gives the overview, switch to challenger mode and probe for blind spots using your methodology: “How exactly will the customer measure success?” “What tells you this contact is truly the Economic Buyer?” “If we speak to the Champion tomorrow, how will you test their power?” "Do we have KPIs or just a gut feeling?" Goal: Don’t corner the rep - get them thinking. Rule of thumb: Keep asking until the rep identifies a clear gap or risk themselves. 3️⃣ Coaching & sparring If something is missing or weak: offer methods or examples. “Many EBs want a clear ROI calc - have you considered adding a simple case study?” Co-create the next step. “How can we ensure you speak with the EB before month-end?” Important: Don’t just hand over the answer - build it together. 4️⃣ Close: Lock in commitments Have the rep state concrete next steps: Not: “Talk to EB.” Instead: “By Friday: EB meeting arranged via the Champion.” Document to-dos in the CRM. Ensure the rep says the commitment out loud. Balance: Structure vs. leadership ✅ Rep leads first: builds ownership and structure. ✅ Manager leads second: through questions and coaching. ✅ Together at the end: clear, dated, owned commitments. Result? Fewer surprises, higher win rates and better forecasting. If your reps leave a deal review without new insight or direction, you’re not coaching – you’re updating. What's your take - any best practices or tips you can share?

We pulled engagement data across hundreds of sales and success teams using SalesHood's Digital Sales Room technology and the patterns are a must share. The teams closing the biggest deals were not the ones creating the most Digital Sales Rooms or uploading the most content. They were the ones building experiences buyers actually came back to - repeatedly. Here is what the data is showing us. There are some great lessons here. 𝐕𝐨𝐥𝐮𝐦𝐞 𝐢𝐬 𝐧𝐨𝐭 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭. Some teams had thousands of Digital Sales Rooms created. Buyers barely opened them. The teams with the highest buyer engagement had far fewer rooms but every one had a clear purpose and organization. More is not more. Intentional is more. 𝐁𝐮𝐲𝐞𝐫𝐬 𝐝𝐨 𝐧𝐨𝐭 𝐰𝐚𝐧𝐭 𝐚 𝐜𝐨𝐧𝐭𝐞𝐧𝐭 𝐥𝐢𝐛𝐫𝐚𝐫𝐲. 𝐓𝐡𝐞𝐲 𝐰𝐚𝐧𝐭 𝐚 𝐠𝐮𝐢𝐝𝐞𝐝 𝐩𝐚𝐭𝐡. We saw some sales teams uploading too many assets and setting up many sites with zero engagement. The highest engaged accounts and the ones that closed did the opposite. They kept it focused. A buyer who feels overwhelmed does not dig deeper, they disengage. 𝐑𝐞𝐩𝐞𝐚𝐭 𝐯𝐢𝐬𝐢𝐭𝐬 𝐚𝐫𝐞 𝐭𝐡𝐞 𝐫𝐞𝐚𝐥 𝐬𝐢𝐠𝐧𝐚𝐥. One of our customers had buyers returning to their deal rooms an average of 90 times per site. That is not a fluke. That is a seller who built something worth coming back to. If your buyer only opens your deal room once, you have a lead. If they keep coming back, you have a real interest and strong buying signals. 𝐌𝐮𝐭𝐮𝐚𝐥 𝐚𝐜𝐭𝐢𝐨𝐧 𝐩𝐥𝐚𝐧𝐬 𝐚𝐫𝐞 𝐚 𝐜𝐥𝐨𝐬𝐢𝐧𝐠 𝐭𝐨𝐨𝐥, 𝐧𝐨𝐭 𝐚𝐝𝐦𝐢𝐧 work. The companies with the highest percentage of deal rooms tied to a mutual action plan also carried the largest average deal sizes. When both sides agree on next steps in writing, deals move. It is that simple. 𝐁𝐮𝐲𝐞𝐫 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭 𝐢𝐬 𝐚 𝐜𝐨𝐚𝐜𝐡𝐢𝐧𝐠 𝐬𝐢𝐠𝐧𝐚𝐥. When hundreds of deal rooms show near-zero buyer activity, that is not a data problem, that's a coaching problem. Managers who track buyer engagement alongside pipeline will catch at-risk deals and unqualified pipeline weeks before they show up as a forecast miss. The best sales teams are not just creating Digital Sales Rooms. They're creating destinations for buying committees. And our data shows exactly who figured it out. Where does your team stand with Digital Sales Rooms today?

You Don’t Just Enable Sellers. You Enable Buyers. Most sales leaders obsess over “sales enablement.” - They train reps. - They equip them with decks. - They feed them scripts. But here’s the truth no one wants to admit: Your reps aren’t the ones who make the buying decision. Your customers are. So why is all your enablement energy pointed inward, when the real leverage is outward? The New Divide 👉 Seller Enablement (Old World) Build playbooks for reps. Train on objection handling. Push more sales materials downstream. 👉 Buyer Enablement (New World) Give customers tools to model ROI themselves. Provide self-service access to information, on their terms, not yours. Create digital workspaces where every stakeholder can collaborate. One focuses on making reps look sharp. The other focuses on making buyers feel confident. Guess which one closes deals faster? The Data 🔹 Dock research shows buyers who receive clear, collaborative resources are 2.5x more likely to advance through the funnel. 🔹 GTM Buddy reports that companies shifting to buyer-first enablement see a 20–30% reduction in sales cycles because decision-makers align faster. That’s not a sales trick. That’s buying confidence at scale. The Blueprint Digital Sales Rooms – Centralized hubs where buyers can access content, proposals, FAQs, and timelines. Self-Service ROI Calculators – Let buyers quantify value without waiting on a rep. Stakeholder Collaboration – Give tools that bring legal, finance, and operations into the process seamlessly. Transparent Roadmaps – Replace pitch decks with mutual action plans that buyers can track in real time. Enablement Beyond the Meeting – Assume 80% of the buying decision happens when your rep isn’t in the room. Build for that. The Identity Shift If your strategy is only to “arm your reps,” you’re behind. Because elite leaders don’t just build better sellers. They build better buyers. - Buyers who feel equipped. - Buyers who feel empowered. - Buyers who feel confident enough to say “yes.” Question for leaders: Are you still enabling your sellers? Or are you finally enabling your buyers? "Lead Different. Sell Smarter. Win with Purpose." --- ��️ Share this with a sales professional who needs to hear it and follow me for more strategies to grow your team 👇 👉 Follow me on LinkedIn: [https://lnkd.in/eejPkWvX) 👉 Beyond The Funnel Newsletter: [https://lnkd.in/eXTPWb9p) 👉 My latest e-Book: https://lnkd.in/eB2HsYqa PS: Thanks for reading!

To be a great sales manager, you have to be a great coach. But coaching often slips through the cracks — especially when there are big deals to close. Now, AI is making it possible for every manager to not just coach more, but coach better. When I was in sales, I saw many new managers fall into the same trap: putting on their superhero cape to rescue deals instead of coaching their reps through them. I was guilty, too! We all knew coaching was important — but we had no time and no tools to scale. With AI, sales managers can now deliver highly targeted coaching at scale. It’s now possible to analyze multiple call transcripts in minutes and pull in unstructured data to understand what happens between calls. You can: 1. Review each rep’s recent calls, emails, and conversations to get a complete picture of how they’re selling — and give them targeted recommendations for improvement. 2. Analyze calls from a specific segment and compare what’s working in closed-won versus closed-lost deals to pinpoint the messaging and strategies that perform best. 3. Generate summaries of how top performers handle objections, communicate ROI, and build a business case — and share those insights with new reps as they ramp. Many HubSpot customers (and our own sales managers) are already using these insights to send regular, personalized coaching to reps — and improve the productivity of their teams. Being a sales manager used to feel like you’re a “super rep” — jumping between calls, rescuing deals, trying to fit in some coaching along the way. Now, it feels like you’re a “super coach” — spotting trends, sharing insights, and helping your whole team scale their impact. Exciting times!