Jayger McGough Tomasino

If your CEO asks for deal updates in Slack, don’t expect reps to update Salesforce. You can throw all the tech, training, and sales ops resources you want at CRM adoption - but if leadership isn’t leading by example, none of it will stick. Here's the tl;dr: Reps don’t hate updating Salesforce because they’re lazy. They hate it because they know no one actually uses it. When leaders bypass the CRM - asking for updates in Slack, emails, or meetings - they send a clear message: “This system doesn’t matter. Your notes don’t matter. Just tell me directly.” And that’s how $100k+ Salesforce investments turn into glorified Rolodexes. So, how do you fix it? 1. Top-down adoption Start with the CEO. If they want deal updates, they need to ask for them in Salesforce. Chatter, Slack integrations, whatever it takes...but it has to flow through the system. 2. Make sales managers accountable Reps won’t change unless their managers enforce it. Run pipeline reviews directly from Salesforce dashboards. No exceptions. If it’s not in Salesforce, it doesn’t exist. 3. Quantify the pain Show reps how missing data costs them deals. Lost follow ups, misaligned hand offs, deals slipping through the cracks...all because the CRM isn’t up to date. 4. Reward the right behaviors Sales culture loves to celebrate closers. But what about the reps who close and keep a clean pipeline? Make data hygiene part of what gets recognized (and compensated). The reality is that CRM adoption isn’t a sales ops problem - it’s a leadership problem. If the top isn’t setting the example, the bottom won’t follow. And until that changes, you’ll keep throwing money at Salesforce while your reps keep their real pipeline in a Google Doc.

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I tracked every deal for 17 years. Here's the $3.8M discovery that changed everything: Most sellers track 47 Salesforce metrics and master none. Elite performers? They obsess over just 3: 𝐖𝐢𝐧 𝐑𝐚𝐭𝐞 (Mine: 52% → 78%) The truth about which deals you should actually pursue 𝐃𝐞𝐚𝐥 𝐒𝐢𝐳𝐞 (Mine: 3.5x increase) The multiplier that turns effort into wealth 𝐂𝐲𝐜𝐥𝐞 𝐋𝐞𝐧𝐠𝐭𝐡 (Mine: 11 months → 6 months) The velocity that creates compound returns When I finally understood these numbers, everything shifted: • Predicted my quarters with 94% accuracy • Walked away from 80% of "opportunities" • Tripled income while reducing my hours • Built a path to early retirement at 42 But here's what most sellers miss: It's not about having a dashboard. It's about knowing which levers create freedom. Example: Improving win rate by 10% OR increasing deal size by 50%? The math says deal size. Every time. (One client shift = $2.3M difference) Yet 90% of sellers chase more meetings instead. That's why they're still grinding at 50. Ready to stop guessing and start engineering your exit? I documented the exact tracking system that took me from burnout to buyout: → Master Your Numbers, Master Your Destiny: https://lnkd.in/eDhvv5YM 🐝 P.S. This lesson includes my actual tracking dashboard—the same one that revealed my Fortune 500 sweet spot was companies ranked 200-500, not the top 50 everyone else chased.

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As an AE, I used a simple proposal template to close an $8-figure enterprise deal at Salesforce. Here's a breakdown of how it works (watch the vide) 👇 Most sellers are great at pitching features. But the ones who consistently win big deals? They know how to tell a great story. The truth is, executives don’t buy products - they buy confidence. They buy vision. They buy a story they want to be part of. Here’s how I do it 👇 The Story Mountain Framework: 1. Exposition – Introduce the characters and setting. 2. Rising Action – Lay out the challenges and obstacles. 3. Climax – Introduce your solution. 4. Falling Action – Ease the tension. 5. Resolution – End with clarity. I break it all down in this week’s sales training—and for the first time ever, I show you the actual proposal I used. Get a copy of my Killer Proposal Template here: https://lnkd.in/gZ246S-Y

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A common mistake in sales is moving too fast. Prospect asks, “Does your software record calls?” You pounce: “It sure does! Not only that, our AI transcribes calls, logs them to Salesforce with 99% accuracy, and makes everything searchable. It’s amazing. Let me show you!” Prospect replies: “That’s too bad. Legal doesn’t allow us to record calls, even with consent.” Why does this happen? Because your mind was already in the future. Already closing. Already convincing. There’s a phrase in neuroscience: “Neurons that fire together wire together.” If your intent is to sell, your words will follow And people can feel it. That invisible pressure creates commission breath. Same intent. Same habit. Same resistance. The way out? Let go of needing the outcome. Move off the solution. Move into the question behind the question. Same question: “Does your software record calls?” But this time, you respond with presence: “It can. Sounds like call recording is something you’re looking for.” Now the prospect opens up: “Actually, we can’t record calls due to legal.” Now you respond, not react: “You can turn it off at the admin level, so no one can record. Want me to show you?” This is the art of detachment. You’re not pushing. You’re not persuading. You’re understanding. Intent shifts. Behavior shifts. Results shifts.

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How to go from SMB AE to MM AE (In 6 simple steps) 1. Pick a company that actually promotes. If you’re at a place that doesn’t grow fast and doesn’t promote internally, the odds are already stacked against you. You can be a top performer and still wait forever because the culture just doesn’t value internal mobility. You want to be somewhere that expects and plans to promote from within. 2. Get to the top of the leaderboard. Every interview process I’ve ever seen starts the same way. The leaderboard. That’s the eligibility filter. So that’s where 100 percent of your focus should go. Until you're at the top consistently that should be your #1 focus. 3. Be a MM AE before you’re a MM AE Find out what actually matters in MM. What’s different. What’s expected. Bigger, more complex deals. More outbound. More strategy. More multi-threading. Then go get results in those areas while you’re still in SMB. That way in the interview you can say. “Here’s how I’m already doing the mid-market job.” Nothing builds confidence like results. 4. Build real relationships with the MM team. Get close to the MM AEs. Learn what they’re working on. What their priorities are. What tools they’re using. What’s working. What isn’t. So when your interview comes around, it’s clear you already understand the role. You’re not walking into a whole new world. You’ve already been around the team and the expectations. 5. Build your internal brand with the hiring team. This is one of the most underrated moves. Find out the #1 priority for MM. Let’s say it’s outbound. Go get results. And then send a no ask message to the hiring manager: “Hey, I heard outbound was the focus this quarter. Booked 7 meetings this month using my cold call flow. Documented it in a playbook. Thought I’d share in case it’s useful.” That's one of the most gangster things you can do. 6. Prep early. Prep often. Don’t wait for the interview process to start preparing. Start building now. A highlight deck. A deal room. Case studies. References. Anything that strengthens your narrative. So when the interview actually opens up. You already have everything done. You just tweak it. Meanwhile everyone else is scrambling. 7. Have a competitive mindset. This is the part most people avoid saying out loud. But it’s the truth. You’re competing. You need to ask yourself constantly. “If someone else has similar numbers, how do I make the case that I’m better?” - That could be your prep. - Your brand. - Your relationships. - Your execution. What you don’t want to do is assume that great work alone gets you promoted. It can. But it’s not the optimal strategy. The optimal strategy is to think competitively. Strategically. And position yourself to win. What did I miss? - Mike G 👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

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One of our customers kept missing forecasts - A $400M B2B SaaS company - They had the pipeline coverage needed - Reps were updating Salesforce regularly - They were submitting forecasts to the board - Everything looked good right up until the EOQ - And then everything fell apart. Deals were pushed - And the forecast was missed, quarter after quarter Sound familiar? It’s so common it’s a cliche. But I wanted to share how they turned it around. Here’s a breakdown: 𝗘𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴 𝗟𝗼𝗼𝗸𝗲𝗱 𝗚𝗼𝗼𝗱: - Pipeline coverage was good - Reps were logging their activity - Reps were updating their pipeline - And the forecasts looked very solid What was going on? 𝗪𝗲 𝗥𝗮𝗻 𝗮 𝗣𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝗔𝗻𝗮𝗹𝘆𝘀𝗶𝘀: - Deals open at 2x Sales Cycle - $12M - Deals in same stage for +90 days - $10M - Etc. 𝗪𝗲 𝗳𝗼𝘂𝗻𝗱 𝘁𝗲𝗻𝘀 𝗼𝗳 𝗺𝗶𝗹𝗹𝗶𝗼𝗻𝘀 𝗶𝗻 𝗭𝗼𝗺𝗯𝗶𝗲 𝗣𝗶𝗽𝗲𝗹𝗶𝗻𝗲! - Deals that would never close. - That reps just dragged on and on. 𝗪𝗵𝘆? - Reps were incentivized - To maintain pipeline coverage - And to maintain high Close Rates - By not closing out Zombie pipeline So they realigned incentives. And implemented a pipeline hygiene process. 60 Days Later... - Forecasts became accurate - Reps could focus on real deals - Close Rate increased from 5% to 21% No new leads. No new headcount. Just better pipeline management. Can you guess how they realigned incentives? Can you guess how they cleaned up the pipeline? And how they kept it clean? 🤔 We break it all down in this tomorrow’s 📰 𝙍𝙚𝙫𝙊𝙥𝙨 𝙒𝙚𝙚𝙠𝙡𝙮 📰 — including what to audit in your own CRM and how to fix this fast. Subscribe to get it here: https://bit.ly/49RCm0h (Or click the link tomorrow to read it ungated.) ✌️

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AEs & SDRs -- don't overthink outbound this week after a long weekend. Try this: Step 1: Use the 5X5 Method -Pick 5-10 accounts and 3-5 prospects per account to focus on this week -SDRs & High-Velocity AEs → increase the volume. Or, use your sales math to determine the number! How? Use Sales Navigator and these filters: -Job change in the last 90 days (especially from former customers) -Job function + seniority -TeamLink connections Step 2: Know your prospect’s business inside out. -Before reaching out, check: -LinkedIn insights - headcount growth, AccountIQ -Past opps in your CRM, closed/lost notes, email & phone convos -Gong Calls -10Ks, funding, stock price, ChatGPT prompts -Podcasts, press releases, and recent hires (try listennotes) -Competitors & mutual customers -Intent data, Google news, -RepVue, Glassdoor, G2 Reviews Step 3: Sequence all 5 contacts using persona-based outreach. -Having a set number holds you accountable. -Build your sequence/cadence based on persona, not volume. -Use a 14 day mini sequence instead of the 28 day sequences that cause piles of overdue tasks. -Front-load your touches across channels Step 4: Personalize every message using this structure: 1️⃣ Relevance: Why you're reaching out 2️⃣ Problem Statement: One of three key challenges 3️⃣ Solution: How others solve it 4️⃣ CTA: Interest-based, not pushy No tool can help you if your messaging is off—make it buyer-centric and problem-focused. Bonus step: -Send 1 email to each contact -Send 1 connect request to each contact -Comment on 5 LinkedIn posts per day -Send 1 LinkedIn video / voice note after each connect request - not pitching just building problem awareness -Cold call :) -- We can't control a lot in sales, but we can control our effort & systems! Give it a go.

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📣 Salesforce launching Partner Cloud isn’t just a new product drop, it’s a loud, clear signal: Partnerships are no longer back-office. They’re front and center in the GTM stack. Why this matters: → CRMs were never designed for partner motions. We all knew it. Salesforce just admitted it. → PRMs can’t handle today’s ecosystem complexity - data, context, co-sell, influence, service. → Value now comes from owning the full surface area of the customer journey, not just the lead. With Partner Cloud: ✨ We finally get purpose-built tools ✨ Ecosystem data is treated like a first-class citizen ✨ GTM becomes a team sport, not a solo sales act This is exactly the validation partner pros have been working toward. Let’s build accordingly. #PartnerCloud #Salesforce #EcosystemLed #Partnerships #GTM #Alliances #Channels

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RevOps Black Box Horror Stories (is this a thing?) I've seen some WILD custom solutions turn into absolute nightmares when the builder leaves. Here are 3 that still haunt me: 1. The $40K Salesforce "Smart" Lead Router A brilliant engineer built an Apex monster that routed leads based on 47 different criteria including time zones. (If you’re an operator you know that time zones are the hardest thing anyone has ever had to build for, prove me wrong) When she left, it took the new team 2 months and $40K in consulting fees to rebuild it. All this initially save 20K. Plot twist: Right now the best solution is buying a routing tool - but I do think this is RIPE for agentic workflows. This is an area to watch… 2. The Contact Washing Machine that No One Could Update A woman in RevOps built a full contact normalization program in Eloqua. It ran the entire database through complex mapping of job titles, roles, employee counts etc and normalized the values. It was beautiful. It was complex. It was completely undocumented. No one could update logic for new personas or industries. She left for a startup. The start up was Go Nimbly. I am her (I am sorry for what I did, but I stand by how pretty it was) 3. Custom CPQ Solution that halted product launches Someone stitched together a fully customized CPQ solution in Salesforce. It worked for a while. When they left, no one knew: - How to add a product - How to update pricing It delayed product launches for MONTHS. Took 3 consultants and $120K to untangle and rebuild. ✨ The Pattern? Every single one started with "Don't worry, I'll document it later." Spoiler: They never did. The technical renaissance in RevOps is exciting. I can't wait to build more. But please, for the love of all that is holy, document your beautiful monsters. Who else has inherited a black box? Who else knows that their name is forever crystalized in a salesforce component they wish they could deprecate? Drop your horror stories below - be honest, what did you leave behind at your last job... I'll share the worst ones in my newsletter (sign up coming soon... very excited)

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I used to think Salesforce Admins just managed users and built reports. Then I watched one rebuild an entire lead routing system, align it with GTM strategy, and train 80 reps. All while chasing down broken integrations they didn’t own. That’s when it hit me: Salesforce Admins aren’t admins anymore. They’re product managers. They’re data strategists. They’re change agents. But most are still stuck using tools, and getting treated, like it’s 2013. AI, automation, and platform complexity have completely changed the job. The title just hasn’t caught up yet. If you're still underestimating your Admins, you're already behind.

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I don’t know about you, but I miss the days when software had an opinion. Software companies that weren't afraid to say “This is how you get the best results from our software.” Some of the most successful products of the last few decades were opinionated. ➡️ Salesforce believed sales was a disciplined, forecastable process — and it baked that belief into stages, pipelines, and forecasting. ➡️ HubSpot (10+ years ago) believed inbound marketing was the growth engine. Attract → Convert → Close wasn’t just messaging — it was how the product worked. ➡️ Basecamp believed simplicity beat power. So it removed features, limited choice, and forced focus. Fast forward to today, and most tools proudly avoid having a point of view. Take Clay. It’s incredibly powerful but they're proudly marketing that you need a "go-to-market engineer" to get it setup. We needed consulting and ~2 months to get it live in a way we felt good about. Or take HubSpot now. Still a great platform — but very different. Where it once said “here’s the inbound playbook,” it now says “here are 239 features and a blank database — configure it however you want.” I don't like this new world. When software refuses to have an opinion: • Companies have no idea how they need to change in order to get the most out of the software • Teams get stuck making a million decisions before they see value • Expensive, specialized experts are needed to get it configured Over the years here at Databox, we’ve developed some strong opinions about how companies should use data: • Strategy and planning must come before execution — the team's belief drives results and enables accountability. (This is why we built OKR management into our software.) • Goals should be grounded in what’s realistic, using data & modeling. (This is why we built forecast modeling.) • Company performance should be shared transparently (This is why we put so much emphasis on our sharing capabilities like alerts, scorecards, mobile app, tv view, shareable dashboards, reports, etc) • Data informs decisions, but never replaces observations of customer, competitive, or market behavior. Reporting requires this context, not just data analysis. This is why we built our Reports feature.) We’ve encoded these beliefs directly into Databox and we teach how to live and breathe them in our Predictable Scale methodology. If you disagree with us, you shouldn't take our free, Predictable Scale course: https://lnkd.in/eScK5VX9 You shouldn't start a trial of our product: https://databox.com/signup Opinionated software isn’t for everyone. But a lot of times, “flexible” just means: you’re on your own. I don’t miss the days when software was less powerful. I miss the days when it was willing to lead.

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Discovery isn’t just a stage in Salesforce is where deals are won. real discovery is about going deep, not wide. It’s about disqualifying the wrong deals early, so you can double down on the right ones. Here’s some questions I use that have improved my discovery game 1. Start with their words, not your pitch “Can you walk me through what’s not working today?” Let them talk. You learn more from their story than from your assumptions. The best insights come from their language, not yours. 2. Time reveals pain “How long has this been a problem?” Pain gets worse with time. If it’s been there for months or years, it’s real. If it’s new, it might fade. The longer the pain, the more urgent the fix. 3. Confirm they’ve tried and failed “What have you tried to solve it?” If they’ve tried and failed, you know it’s not just a passing thought. It’s a real problem. This is where deals get real. 4. Find the personal impact “How is this impacting you personally?” This is the gold. Business pain is one thing. Personal pain is another. People move when it hurts them, not just the company. 5. Tie your solution to their success “If we could solve this, what would that mean for you and the team?” Now you’re not just selling a product. You’re selling a better future, in their words. This is where urgency and buy-in are born. The best sellers know: slow is smooth, smooth is fast. Go deep. Disqualify fast. Win more. What’s one question you ask that always opens things up?

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Sales motions are now multi-faceted. What used to be a simple CPQ vendor selection decision is now a strategic conversation about how to support every revenue motion - across every channel, pricing model, and customer expectation. Today’s buyers don’t follow one path. They navigate through: 🎯 Sales-led teams 🎯 Partner channels 🎯 PLG motions - buying directly inside your product 🎯 Self-service portals and eCommerce sites 🎯 Marketplaces With the increasing adoption of Agentic AI for Sales, this omni-channel approach just became more nuanced. We acknowledge this new reality, and have added to the foundation layer the introduction of API-based Headless Quoting. It enables you to extend the power of CPQ into any interface your buyers engage with, whether it’s inside your product, a partner portal, a marketplace, or even through an AI agent. The buyer must experience all of these sales channels with an equal measure of continuity. 👉 Where we sell is changing 👉 How they buy is changing 👉 How we price must change too... Today’s revenue models are now more dynamic than ever: 🎯 One-time purchases 🎯 Milestone-based deals 🎯 Subscriptions with multi-year ramps 🎯 Tiered or usage-based pricing 🎯Overage models and hybrid billing cycles Amid all this complexity, one thing remains - you still need a powerful configurator at the core to build accurate, scalable quotes. It must be intuitive to use and manage. It must be the first thing you get right in your Revenue stack. 👉 Traditional CPQs don't cut it. That’s why DealHub redefined the modern rev-tech stack. CPQ is no-longer the unreliable uncle of the family, our AI-Powered CPQ is the catalyst for the entire revenue-lifecycle working together as one. At DealHub.io we are not offering a better revenue platform (yes we have that!) - we are sharing a different vision for what intrepid GTM execution looks like. Our customers are gaining revenue autonomy across the business. “Getting our sellers into DealHub gave them autonomy over their customer proposals, over the pricing that was available at their fingertips. It allowed my team, my deal desk team to focus more on innovation, more on pricing strategy, more on creative deal making. And that's ultimately what my team is about and what excites us…”  -- Lucy Anne Link, Deal Desk Manager, Intuit Learn more about our new capabilities here 👉 https://dealhub.io/

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