Scenario-Based Pitching

Here's why most reps (and I'll even say most managers) hate role plays. It's because they've been done the wrong way for so long. How most role play sessions go. 1. There is no prep. Rep doesn't know what they are working on. 2. It's not a real account/name/situation they are practicing (I messed this up for YEARS my teams pitched to superbizz for like a decade) 3. It's the full call which not only doesn't full count as practice but even worse... 4. Only 1 repetition. They only get to do it once. 5. Then there is a TON of feedback given, like waaaaaay to much feedback given. Most of it negative or areas to improve. 6. They never actually get to apply that feedback in practice, they are sent out into the game again. 7. BONUS - It's done in front of a large group peers (hot seats anyone) - that is not practice, that's a performance. -- So yeah... No wonder reps and managers dont like practice. What's funny is a very large (not all mind you) but very large % of sales people played a sport or instrument going up. Think about how THOSE practices were run and you can improve your sales practice immenselye. Structured - Set time. Set place. Scenario Based - Pick real scenarios and situtations. SKILL Based - What skill are you working on (the call is not the skill) For UPCOMING games/performances - Pick a a call coming up/an account they are targeting. Chunked - Skills and Drills - Just the disco questions, JUST 2 objections. Short Punchy Feedback - More doing, less talking. - That was good! Do it again, try this! High Energy - This is key! HIGH Repetition - When chunking you can get 4-5 (often times more) repetitions in that same session. THAT is how you practice. That is how you actually can improve skills quickly. Implement that and not only does practice get better... But so do your people!

You’re a detective. You walk into a crime scene and say: “I already know who did it! It was the guy in the hat! Here’s why, here’s how, and here’s what you should do about it!” What happens next? The witnesses shut down, the clues get overlooked, and the case goes cold. That’s what pitching feels like on a cold call. It’s jumping to conclusions without understanding the situation. Instead, take the detective approach: start with a provactive question to gather clues. For example, if you’re a salesperson for CaptivateIQ, you might ask: “When your reps ask about commissions, can they check their numbers anytime, or do you just send out statements as needed?” Then, shut the front door. You’re not pitching. You’re poking the bear. You’re asking a question that makes people think differently about their current solution. Why? Solutions have no value with a problem. Detectives don’t rush—silence is where the evidence surfaces. Once you have their response, dig a little deeper: “You’ve probably looked into automating this at some point.” And pause again. A good detective knows the importance of letting the suspect (or prospect) fill the gaps. If they’ve explored solutions but haven’t made a move, investigate further: “Seems like there was a reason it didn’t work out.” Then zip it. The more you listen, the more they’ll reveal. Cold calls aren’t about solving the case in one breath. They’re about piecing together the story one clue at a time. It’s not your job to fill people’s heads with information. Your job is to draw it out. Poke the bear. Case closed.

Think Like a CFO. Show the Math Behind Your Pitch. Derisk Investments. Two recent conversations remind me to keep beating the risk drum.   𝗧𝗵𝗲 𝗳𝗶𝗿𝘀𝘁 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻 𝘄𝗮𝘀 𝘄𝗶𝘁𝗵 𝗻𝗲𝘄 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀. After bootstrapping their concept, they're seeking funding.   "Our total market is HUGE. We're going to ask for $12M," said the founder.   Let's stop right there.   The fallacy of a huge Total Available Market is a common misconception.   So is the thinking that a great idea can go from zero to hero without proving unit economics first.   𝗧𝗵𝗲 𝘀𝗲𝗰𝗼𝗻𝗱 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻 𝘄𝗮𝘀 𝘄𝗶𝘁𝗵 𝗻𝗲𝘄 𝗺𝗮𝗿𝗸𝗲𝘁𝗲𝗿𝘀. We discussed becoming T-shaped and developing financial acumen. • The "growth at all costs" era is dead. • Every dollar gets scrutinized. • Boards demand unit economics. • CFOs have final say on budgets.   𝗪𝗵𝗮𝘁 𝗱𝗼 𝗯𝗼𝘁𝗵 𝗼𝗳 𝘁𝗵𝗲𝘀𝗲 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻𝘀 𝗵𝗮𝘃𝗲 𝗶𝗻 𝗰𝗼𝗺𝗺𝗼𝗻?   Neither group spoke CFO. The founders led with market size, not market capture. The marketers discussed campaigns, not the impact on cash flow.   𝗕𝗼𝘁𝗵 𝗺𝗶𝘀𝘀𝗲𝗱 𝘁𝗵𝗲 𝗳𝘂𝗻𝗱𝗮𝗺𝗲𝗻𝘁𝗮𝗹 𝘀𝗵𝗶𝗳𝘁: CFOs don't care about your TAM. They care about your path to profitability. ------------------------------------------------------- "Marketers think CFOs want fireworks. CFOs actually want fireproofing." ------------------------------------------------------- 𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝗖𝗙𝗢𝘀 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝘄𝗮𝗻𝘁 𝘁𝗼 𝘀𝗲𝗲:   𝗙𝗿𝗼𝗺 𝗙𝗼𝘂𝗻𝗱𝗲𝗿𝘀: → Unit economics that work at scale → Customer acquisition cost vs lifetime value → Clear path from $0 to break-even to profit → Scenario planning: best/base/worst case → Kill criteria if metrics don't hit targets.   𝗙𝗿𝗼𝗺 𝗠𝗮𝗿𝗸𝗲𝘁𝗲𝗿𝘀: → Marketing effectiveness models → Customer acquisition cost by motion and campaigns → Pipeline contribution and sales cycle impact, including time lag → Budget allocation based on performance data → Risk mitigation strategies for underperforming campaigns.   𝗧𝗵𝗲 𝘀𝗶𝗺𝗽𝗹𝗲, 𝗯𝘂𝘁 𝗼𝗳𝘁𝗲𝗻 𝗺𝗶𝘀𝘂𝗻𝗱𝗲𝗿𝘀𝘁𝗼𝗼𝗱 𝘁𝗿𝘂𝘁𝗵: • Your beautiful pitch deck means nothing if the math doesn't work.    • Your creative campaign is worthless if you can't prove the path to a business outcome.    • CFOs live in a downside-first world. They ask: "What's the worst that could happen?" Not: "What's the best we could achieve?"   𝗪𝗵𝘆 𝘁𝗵𝗶𝘀 𝗺𝗮𝘁𝘁𝗲𝗿𝘀 𝗿𝗶𝗴𝗵𝘁 𝗻𝗼𝘄: • Interest rates aren't zero anymore. Capital isn't free. Every investment competes with risk-free returns.    • The companies that get funded speak CFO fluently while maintaining founder vision.   The future belongs to those who think like CFOs while dreaming like visionaries. Show the math behind the magic. Derisk the investment. Make the downside manageable. That's how you win in 2025.   What's your experience? Are you speaking CFO or still selling sizzle? #GMT #risk #CMO #leadership  

Sales Projections: Strategy or Speculation? Let’s be honest — I’ve seen far too many sales projections that look more like wishful thinking than strategic planning. A bold number on a slide — “We’ll hit $1M next quarter.” Everyone nods, the target is set, and the meeting moves on. But here’s the hard truth: A projection without a strategy is just a guess. I’ve learned this the hard way. Early in my career, I witnessed a team miss their quarterly target by a huge margin — not because they didn’t work hard, but because their projections were built on gut feel and blind optimism. No alignment between sales goals and actual pipeline health. No consideration for changing customer behavior or market dynamics. No breakdown of how deals would move through the funnel. It wasn’t a forecast — it was a hope-cast. So, how do seasoned sales leaders project with precision? It boils down to three strategic pillars: 1️⃣ Market-Driven Insights Your projections must start outside your company, not inside. What’s happening in your industry? How are customer priorities shifting? Is there economic turbulence or competitive disruption? Sales doesn’t operate in a vacuum — your projections shouldn't either. 2️⃣ Pipeline Precision A projection isn’t a random target — it’s a sum of its parts: How many deals are in each pipeline stage? What’s your historical win rate? What’s the average deal size and velocity? Bottom-up forecasting — where data, not hope, dictates the number — is the only way to build credibility. 3️⃣ Scenario-Based Planning Smart leaders never project a single number — they project a range: Best case: If high-value deals close faster than expected. Worst case: If key prospects stall or drop out. Most likely case: Where the current pipeline trends realistically point. This isn't playing it safe — it's playing it smart. What happens when you adopt this approach? Your sales team knows exactly what they’re working toward. Leadership has confidence in the numbers. You shift from chasing targets to executing a clear, strategic plan. Because at the end of the day — sales projections aren’t about predicting the future, they’re about engineering it. Would love to hear from my network — how do you balance optimism and realism in your sales projections? Let’s discuss. #SalesLeadership #StrategicProjections #RevenueGrowth #SalesStrategy

Last year, a head of sales at a fast growing Swedish scale-up told me: “We have great meetings. Prospects nod, say they’re interested… and then nothing happens. The deal drags on, and eventually, we lose to ‘no decision.” Sound familiar? 🤔 I asked him: “What story is your buyer already living?” Because here’s the thing: people don’t buy based on logic alone. They buy based on the story they’re telling themselves about their company, career, and industry. The head of sales used to sell their SaaS platform (to CFOs) by pitching automation, efficiency, and cost savings. But the CFO wasn’t living in the “efficiency story”. His story was about “career risk”. Imagine being the CFO of a company for 12 years. You've seen other executives bet on tech and fail. Your internal monologue won't be about “How do I automate?” but rather “How do I not screw this up?” 💡So we just flipped the approach: 🍃 Instead of pitching a “faster, better” solution, we positioned the SaaS platform as the safest path forward, backed by industry adoption, risk mitigation, and CFO peers he could relate to and who already had taken the leap. 🍃 Instead of selling benefits and features, we created a narrative together with the potential buyer, one that made him the strategic leader who future-proofed the company without taking unnecessary risks. 🍃 Instead of pushing for an immediate decision, we helped him build a Fundamental Messaging Tree that he could use to educate internally, thus he became the champion of the deal. The outcome? -> This strategy (combined with a media orchestration of hyper-targeted media ads scaling the head of sales) just resulted in a high figure deal closed, without an RFP. 👉 If you’re in B2B sales and your deals are stalling, ask yourself: “What story is my buyer already living? Are you selling against it, or working with it?” ☔ The best sales professionals don’t force new stories. They fit into the ones buyers already believe in and tell themselves. #Sales #Storytelling #messaging #EnterpriseSelling #Megadeals #Rainmakers

The best sales engineers ASK before they SHOW. At some point in every demo your prospect is going to ask: “Does your product do XYZ?” What you do next can make 😀 or break 😢 the deal. Story time! SCENARIO 1: You are giving a demo and your prospect asks, “Does your product support role-based access controls and permissions?” Your product does support RBAC, so you excitedly say, “Yes! Let me show you!” You immediately proceed to show how to set up user roles and teams and data permissions. You log in as a user from EMEA and show how they only can see data for EMEA. You log in as a user from APAC and show how they only can see data for APAC. You then log in as the Global VP user and show how she can see all the data. Ta-daaaa! 😀 You ask, “Now that I have showed you our RBAC capabilities, can you see how they would help you restrict access to your data across your teams?” Your prospect responds with a frown 🙁, “That doesn’t work for us. We are an open team and everyone should have access to all data. Looks like a lot of complexity that we do not need nor would want to pay for.” You sadly 😢 realize that you: ❌ Wasted 10 minutes of valuable demo time ❌ Made your product seem more complex than it is ❌ Got your prospect thinking that they are going to be overpaying for features that they don’t want SCENARIO 2: You are giving a demo and your prospect asks, “Does your product support role-based access controls and permissions?” Your product does support RBAC, but you calmly say, “I’m curious about that. Can you tell me more about your RBAC needs?” Then you wait… Your prospect responds, “We are an open team and everyone should have access to all data. I want to make sure that my team doesn’t have to jump through a bunch of hoops to get access to the data they need.” Knowing the reason behind their question, you confidently say, “The default setting in our product is that everyone has access to all data. No hoops. No jumping. No configuration required. Just instant access for everyone to all data.” Your prospect replies, “That’s perfect. Exactly what we need right out-of-the-box! I looked at one of your competitors, and their product seemed really complex. Lots of configurations that we don’t need. You seem like a much better fit so far.” You smile 😁 as you realize that you: ✅ Showed how your product meets your prospect’s needs (without even showing anything) ✅ Saved 10 minutes of valuable demo time ✅ Got your prospect thinking how easy your product is to use ✅ Created a competitive differentiator (even if your and your competitor’s products have the exact same RBAC features) ASK before you SHOW! 🙌

I was speaking with someone a few days ago about FAB (Features, Advantages, Benefits), and then it struck me—how often we skip straight to features and wonder why sometimes our pitches don’t resonate with the customers. The truth? Features might inform, but it’s the benefits that sell. Here’s the breakdown: Features are the specs, processes, or tools behind the service—important for credibility, but not what convinces a client. Advantages start to show why our approach or tools stand out compared to alternatives. This is good, but it often doesn’t spark that client “aha” moment. Benefits? That’s where we connect to the client’s needs, aspirations, and goals. Benefits say, “Here’s how our service makes a real impact on your business.” Take, for example, a supply chain visibility solution: - Feature: Real-time, end-to-end visibility across the supply chain. - Advantage: Enables faster response to disruptions than standard reporting. - Benefit: Reduce stockouts, improve customer satisfaction, and build a resilient brand that’s prepared for the unexpected. So, how do you implement FAB effectively? 1. Customize for Each Client: Benefits vary depending on the client’s priorities. For a premium brand, it might be about “ensuring product availability for demanding customers.” For a value-oriented brand, it could be “optimizing costs through efficient inventory management.” Speak to each client’s unique goals. 2. Tell a Story: Clients remember scenarios, not specs. Frame FAB through real-world examples that show how your service addresses their specific challenges. Example: For a client struggling with fluctuating product availability, share a story about another brand that used real-time visibility to catch bottlenecks before they happened, keeping shelves stocked even during a sudden demand spike. Relate how this enhanced customer loyalty and built trust in the brand’s reliability. By crafting a vivid scenario around FAB, you help the client picture your solution working for them, making the benefits tangible and memorable. 3. Balance in Messaging: FAB is perfect for deep dives like presentations or proposals, but in shorter interactions, focus on benefits and let features and advantages subtly support. Example: In a short pitch, instead of listing “real-time visibility” (feature) or “faster response times” (advantage), highlight how “our solution ensures shelves stay stocked and customers keep coming back” (benefit). You might briefly mention the underlying feature (“using real-time data”), but let the benefit drive the message. This way, you’re speaking directly to the client’s goals, catching their attention with what matters to them most, and making a memorable impact, even in a short touchpoint. When talking about services, lean heavily into benefits. Clients want to see how your services drive tangible impact—not just what’s under the hood. How have you used FAB in your pitches? #cpg #cpgindustry #consumerproducts

One change to our pitch took Sherlocks.ai from 1 interested person per 10 conversations to 5. Before, every demo looked the same. Same incident scenario, same stack, same walkthrough, regardless of who was in the room. We switched to demoing Sherlocks inside their environment. If they used Datadog, we ran the demo on a Datadog alert. If they ran microservices on AWS, the scenario used their setup. If they'd recently dealt with a painful outage, that's what we walked through. The product and pitch stayed identical, only the examples changed. Your buyer doesn't need to understand your product in theory. They need to see their exact problem inside it. When they do, the conversation changes completely. If you're selling a technical product, are you showing examples in their language or yours?

In a room full of vendors promising the moon, be the one who delivers next Tuesday. Your biggest competitive advantage in health tech isn't your AI, your algorithms, or your innovation. It's being the one vendor who doesn't overpromise. I've sat through several dozen vendor showcases in my career. However, last month's showcase was not typical (mainly because it was onsite which I rarely get to do anymore). However, the pitches were more of the same. Every company claimed they would "transform healthcare delivery" and "revolutionize patient outcomes." The winner? The company that said: "We'll reduce your lab turnaround time by 23 minutes and save you $47 per test. Here's exactly how." Why underpromise-overdeliver wins in healthcare: ▶️ Scenario A (The Overpromiser): "Our AI will revolutionize your clinical workflows!" Reality: 6-month implementation, marginal improvements, lots of training and adoption issues with the end users ▶️ Scenario B (The Realist): "We'll cut your documentation time by 12 minutes per patient encounter" Reality: 8-minute savings achieved in month 2, plus unexpected workflow benefits Guess who gets the renewal? The Reality-Based Messaging Framework: ✓ Specific metrics instead of broad promises ✓ "Typically" and "on average" instead of "always" ✓ Implementation timelines with buffer built in ✓ Clear scope limitations upfront The counterintuitive result: When you set realistic expectations, buyers trust you with bigger opportunities. In a market drowning in AI vaporware and "revolutionary" claims, being the vendor who tells the truth—even when it's less sexy—is refreshingly sellable. Your credibility is your moat. Protect it fiercely.

Your pitch keeps falling flat because you're pitching to the wrong stage. Every prospect sits in one of 5 stages. And each stage requires a completely different approach. Here's how to identify where they are. And what to do about it. STAGE 1. UNAWARE What they say: "We're not really looking at anything right now." What it means: They don't know they have a problem. Your move: Educate. Share insights. Plant seeds. Don't pitch. STAGE 2. PROBLEM AWARE What they say: "Yeah, we've noticed some issues but it's not a huge priority." What it means: They know something's off. They don't think it's serious. Your move: Expand the pain. Ask impact questions. Help them see how big it actually is. STAGE 3. SOLUTION AWARE What they say: "We've been looking into some options." What it means: They're researching. They're open to conversations. Your move: Differentiate. Show them why your approach is different from the other options they're seeing. STAGE 4. YOUR SOLUTION AWARE What they say: "We've heard good things about you. Tell me more." What it means: They know you exist. They're evaluating. Your move: NOW you can pitch. Tie everything back to their specific problems. STAGE 5:.MOST AWARE What they say: "We're ready. What are the next steps?" What it means: They're sold. Just need logistics. Your move: Close. Don't oversell. Make it easy. The mistake most reps make? Pitching in stage 1 or 2. You can't sell a solution to someone who doesn't believe they have a problem yet. Meet them where they are. Move them to the next stage. Then the next. That's how deals actually close.