Lessons Learned from Revenue Problem Solvers Podcast

The "Gotta Believe" framework changed how I evaluate every opportunity and it might just save you from your next career disaster. 😵 I had a thought-provoking conversation with Jason Gelman on the podcast this week. His journey from scaling Compass from $100M to $6B ARR as the head of revenue strategy and operations to joining Primary Ventures offers a unique perspective on revenue leadership. What particularly resonated was Primary's "Gotta Believe" framework for evaluating opportunities. It's a refreshingly honest approach that explicitly acknowledges the key assumptions and risks in any major decision. As Jason explained, "We have an investment thesis but the 'Gotta Believes' are the unanswered questions, the risks. If this business is going to be successful, you gotta believe that X will happen, Y will happen." I've found this framework equally valuable for revenue leaders weighing career moves or major strategic initiatives. By explicitly listing what "must be true" for success - whether about product evolution, competitive dynamics, or market timing - we can better quantify risk and identify the critical variables to test. It forces a level of intellectual honesty that's often missing in high-stakes decision-making. Here are my other key takeaways from our conversation: 1. Financial fluency is what separates tactical sales leaders from strategic executives. Jason noted that "the hardest skill set to find in a CRO is someone who is deeply analytically fluent and P&L fluent." This aligns with SBI's research showing top CROs spend 20% more time analyzing business performance data. 2. Brute-forcing growth without product-market fit creates unsustainable pressure. We both shared war stories of scaling revenue teams prematurely, and the burnout that inevitably follows when selling products with marginal fit. The psychological toll on these teams is substantial. 3. VC networks provide information asymmetry that most operators don't fully appreciate. The access to back channels, private information, and talent placement creates opportunities for those who actively cultivate these relationships - even when you're not job searching. 4. AI is creating a rare window of disruption in the GTM tech stack. As Jason noted, "If you ever wanted to unseat Salesforce, this is the only time I've ever seen where there's this window where it could possibly happen." The challenge is determining which emerging tools to adopt now versus which to wait on. This was an awesome conversation and I hope you enjoy as much as I did! Also, if you're enjoying the pod, please give us a rating or review on your favourite podcast platform!

Most CROs are stuck playing Whac-A-Mole. Pipeline dips. They panic. They spin up new campaigns. Deals stall. They blame the team. They change the comp plan. Forecast misses. They scramble. They push harder on the same broken levers. This is what happens when you lead departments instead of building systems. We recently had Aviv Canaani, CMO/CRO of Datarails, on our podcast. His team grew new sales 90% YoY. Not because they worked harder. Because they stopped thinking like department heads. Here's what that actually means: They connected the entire revenue chain: - Marketing didn't just generate leads - They mapped spend to meetings to pipeline to revenue - Sales didn't just work opportunities - They fed insights back to optimize the top of funnel - RevOps didn't just run reports - They turned data into capacity planning decisions When meeting volume spiked, they didn't let it become a bottleneck. They pushed HR to hire faster. When demo requests came in, they didn't let them sit. They built a five-minute SLA and next-day availability. When forecasting felt like guesswork, they didn't accept it. They built conversion benchmarks tied to historical data. Every part worked together. Like a factory line, not separate departments. Most revenue leaders are optimizing individual functions: - Better marketing campaigns - Better sales training - Better CS processes But they're not connecting them into one engine. So when one part improves, another breaks. When demand spikes, capacity can't handle it. When data is needed, it's not trustworthy. That's the difference between tactics and architecture. Tactics fix today's problem. Architecture prevents tomorrow's fire. Are you building systems or managing departments? 🤔 More on this in our last issue of 📰𝙏𝙝𝙚 𝙂𝙏𝙈 𝙎𝙘𝙞𝙚𝙣𝙘𝙚 𝘽𝙧𝙞𝙚𝙛 📰 Get it here: https://bit.ly/4inXUXG Listen to the full podcast episode on 📰𝙂𝙏𝙈 𝙎𝙘𝙞𝙚𝙣𝙘𝙚 📰 here: https://bit.ly/4rgmRYO ✌️

Most revenue problems aren't revenue problems. They're process problems wearing a revenue problem disguise. I've spent the last 20 years inside growth-stage companies — as an operator, a consultant, and now as VP of RevOps at Ordergroove. And the pattern I see most consistently isn't that companies lack ambition or talent. It's that they've outgrown the way they operate, but haven't updated the operating system. Here's the 3-question audit I use to identify where the real friction is: QUESTION 1: Can every rep on your team describe your sales process in the same order? Not roughly the same. Exactly the same. If you ask five reps how a deal moves from first call to close, and you get five different answers, you don't have a sales process — you have five individual approaches that happen to close some deals. That's not a sales team. That's a collection of salespeople. What to do: Run the exercise. Ask three reps to walk you through a deal from start to finish. Record the differences. Those gaps are your starting point. QUESTION 2: Does your manager spend more time coaching or reporting? This one stings, because in most companies, managers spend the majority of their time building slides for leadership, pulling data that doesn't exist in dashboards, and sitting in meetings that don't move anything. That time comes directly out of coaching. And coaching is the single highest-leverage activity a sales manager can do. What to do: For one week, have your managers track how they actually spend their time. The results are always illuminating — and rarely comfortable. QUESTION 3: When a deal dies in late stage, do you know why? Not "the prospect went cold" or "they chose a competitor." Those are symptoms. Why did they go cold? What did the competitor offer that you didn't? What signal did you miss at discovery? If your CRM doesn't capture this in a structured way, you're flying blind on your biggest deals. What to do: Add two required fields to every closed-lost record: root cause category (5–7 options) and a single free-text field for the rep's real answer. Review monthly. Patterns will emerge within 60 days. These aren't complex fixes, but they require someone to own them — and in most growth-stage companies, no one does. That's usually where the work starts. If any of this hit close to home, I'd genuinely enjoy a conversation. I love talking shop and sharing experiences to see what we can learn. Shoot me an email or a DM on LinkedIn and we'll set something up. — Rich P.S. If you're not already listening to The Midgame Mindset, we've been putting out some strong episodes lately on sales culture, GTM design, and the operator's mindset. Find it on YouTube, Spotify, Apple or wherever you get your podcasts.

𝗧𝗵𝗲 𝗥𝗲𝘃𝗲𝗻𝘂𝗲 𝗣𝗿𝗼𝗯𝗹𝗲𝗺𝘀 𝗬𝗼𝘂 𝗖𝗮𝗻'𝘁 𝗙𝗶𝘅 𝘄𝗶𝘁𝗵 𝗠𝗼𝗿𝗲 𝗣𝗶𝗽𝗲𝗹𝗶𝗻𝗲 Every time a number slips, the default reaction is predictable: “𝗟𝗲𝘁’𝘀 𝗽𝘂𝘀𝗵 𝗳𝗼𝗿 𝗺𝗼𝗿𝗲 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲.” It’s easy to say. It looks responsible. It keeps the execs calm. But it’s also the fastest way to hide the real problem. With 25 years of running GTM across markets, here’s the uncomfortable truth: 𝗦𝗼𝗺𝗲 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 𝗽𝗿𝗼𝗯𝗹𝗲𝗺𝘀 𝗮𝗿𝗲𝗻’𝘁 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝗽𝗿𝗼𝗯𝗹𝗲𝗺𝘀. 𝗧𝗵𝗲𝘆’𝗿𝗲 𝘀𝘆𝘀𝘁𝗲𝗺 𝗽𝗿𝗼𝗯𝗹𝗲𝗺𝘀 𝗺𝗮𝘀𝗾𝘂𝗲𝗿𝗮𝗱𝗶𝗻𝗴 𝗮𝘀 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝗴𝗮𝗽𝘀. If you don’t diagnose the system, no amount of top-of-funnel volume will save you. Here are the five system failures I see most often: 𝟭. 𝗗𝗲𝗮𝗹𝘀 𝗮𝗿𝗲𝗻’𝘁 𝘀𝘁𝗮𝗹𝗹𝗲𝗱. 𝗬𝗼𝘂𝗿 𝗰𝗼𝗻𝘀𝗲𝗻𝘀𝘂𝘀 𝗽𝗮𝘁𝗵 𝗶𝘀. Most teams obsess over “next steps” with one person. But the average buying group is now 6–10 stakeholders (Gartner, 2023). In Japan, ASEAN or Korea, your deal isn’t stuck because of price - it’s stuck because your internal champion ran out of political currency. 𝗠𝗼𝗿𝗲 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝘄𝗼𝗻’𝘁 𝗳𝗶𝘅 𝗮 𝗰𝗼𝗻𝘀𝗲𝗻𝘀𝘂𝘀 𝗯𝗹𝗶𝗻𝗱 𝘀𝗽𝗼𝘁. 𝟮. 𝗪𝗶𝗻 𝗿𝗮𝘁𝗲𝘀 𝗱𝗼𝗻’𝘁 𝗱𝗿𝗼𝗽 𝗯𝗲𝗰𝗮𝘂𝘀𝗲 𝗼𝗳 𝗰𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗼𝗿𝘀. They drop because of internal confusion. Confusion around ownership. Confusion around messaging. Confusion around what “𝘨𝘰𝘰𝘥” looks like. When teams guess, velocity dies. When roles are clear, revenue moves. 𝗣𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝘄𝗼𝗻’𝘁 𝘀𝗼𝗹𝘃𝗲 𝗮 𝗰𝗼𝗵𝗲𝗿𝗲𝗻𝗰𝗲 𝗽𝗿𝗼𝗯𝗹𝗲𝗺. 𝟯. 𝗙𝗼𝗿𝗲𝗰𝗮𝘀𝘁 𝗺𝗶𝘀𝘀𝗲𝘀 𝗮𝗿𝗲𝗻’𝘁 𝗮𝗯𝗼𝘂𝘁 𝗼𝗽𝘁𝗶𝗺𝗶𝘀𝗺. They’re about missing signals. If your team can’t articulate: • the customer’s political reality • the internal blocker • the decision sequence …then your forecast is just feelings in a spreadsheet. 𝗠𝗼𝗿𝗲 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝘄𝗼𝗻’𝘁 𝗳𝗶𝘅 𝗮 𝗯𝗹𝗶𝗻𝗱𝗻𝗲𝘀𝘀 𝗽𝗿𝗼𝗯𝗹𝗲𝗺. 𝟰. 𝗥𝗲𝘃𝗲𝗻𝘂𝗲 𝗱𝗼𝗲𝘀𝗻’𝘁 𝗰𝗼𝗹𝗹𝗮𝗽𝘀𝗲 𝗮𝘁 𝘁𝗵𝗲 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿. It collapses in the handoffs. Marketing → SDR → Sales → CS → Partners Every clumsy transition is a leak. Every misaligned expectation is a tax on momentum. 𝗠𝗼𝗿𝗲 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝘄𝗼𝗻’𝘁 𝗳𝗶𝘅 𝗮 𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗮𝗹 𝗹𝗲𝗮𝗸. 𝟱. 𝗠𝗼𝗺𝗲𝗻𝘁𝘂𝗺 𝗱𝗶𝗲𝘀 𝘄𝗵𝗲𝗻 𝘁𝗲𝗮𝗺𝘀 𝗹𝗼𝘀𝗲 𝗰𝗼𝗻𝘁𝗲𝘅𝘁. Velocity isn’t speed. Velocity is shared understanding. When teams know: • what matters this week • what no longer matters • what to stop doing …execution tightens instantly. Without that? You could triple pipeline and still miss the quarter. 𝗧𝗵𝗲 𝗯𝗼𝘁𝘁𝗼𝗺 𝗹𝗶𝗻𝗲 The real skill for GTM leaders today isn’t creating more pipeline. It’s reading the system underneath the pipeline. Most problems aren’t upstream. 𝗧𝗵𝗲𝘆’𝗿𝗲 𝗹𝗮𝘁𝗲𝗿𝗮𝗹. 👀 𝗬𝗼𝘂𝗿 𝘁𝘂𝗿𝗻: What’s one revenue issue you’ve seen that looked like a pipeline problem - but wasn’t? #GTM #Marketing #SalesPrograms #B2B #APAC #Strategy