Sales Planning

We scored every sales call on preparation quality (1-5 scale) in our dataset. Excellent preparation (5/5): 30% close rate. Poor preparation (1-2/5): 4.4% close rate. A 𝟔.𝟖× 𝐦𝐮𝐥𝐭𝐢𝐩𝐥𝐢𝐞𝐫. But nobody wants to admit this: High-quality preparation is functionally impossible at scale. The math doesn't work. 3-4 calls a day × 30-45 minutes of proper prep = 2-3 hours. Before you even start calling. So your reps skim the website. Glance at LinkedIn. Hope for no surprises. Then the customer asks: "Have you worked with anyone in our space before?" And your rep says: "I'm no real estate expert, but…" Credibility gone. In one sentence. We found this in 𝟒𝟎% 𝐨𝐟 𝐜𝐚𝐥𝐥𝐬—customers had to educate reps on basic facts that 15 minutes of research would have covered. Everyone treats this as a discipline problem. It's an infrastructure problem. Your top rep closed $1.4M last year. Your average rep closed $425K. Same manager, same product. The gap isn't talent. It's accumulated pattern recognition that lives in one person's head. Training says: "Remember to prepare better." Infrastructure says: "Here's what your best rep already knows, ready in 3 minutes." Training hopes reps remember. Infrastructure enables them to execute. Part 2 of our analysis: https://lnkd.in/gsQAFA4M

😅 The Sales Call That Nearly Sank a Million-Dollar Deal (and Taught Me a Lesson I’ll Never Forget) Ever walked into a sales meeting and immediately realized you were wildly underprepared? Yeah... same. Here’s one that still haunts me (but also made me better). It was a last-minute meeting. I came armed with everything I thought I needed—tech talking points, case studies, best practices. Ready to talk about business transformation through technology. What I didn’t do? Ask who would be attending. 🤦♂️ Surprise! In walks the CFO/COO (non-Indonesian, sharp as a blade), looks me in the eye and says: 👉 “So… tell me about my business—and why this solution matters to me?” Boom. Right between the eyes. I was ready to talk features, not finances. Operations, not outcomes. The silence in that room? Deafening. We managed to recover, thankfully. It took multiple follow-ups, tailored value mapping, and deeper conversations—but we closed that million-dollar deal. 🎯 Here’s what I took away: ✅ Know who's in the room. Always. ✅ Execs care about impact, not tech. Speak their language: growth, efficiency, risk, profitability. ✅ Overconfidence ≠ preparation. One gets applause. The other gets you a polite smile and no follow-up. Now I prep for every meeting like the top execs will show up—because sometimes, they do. And they don’t play. #preparationisthemotherofallsuccess Got any similar war stories? I’d love to hear them. #SalesLessons #EnterpriseSales #BusinessTransformation #TechForBusiness #CLevelEngagement #SalesFails #B2BSales #LearnFromMistakes

Winging it comes with a lot of risk. In a complex sales environment, "winging it" isn't just a risky strategy—it is a recipe for a closed door. When you are approaching a new client with a high-stakes deal on the line, your level of preparation serves as the first real indicator of the value you bring to the table. In these initial encounters, you aren't just selling a product; you are selling your own credibility and your right to occupy their time. Deep preparation goes far beyond a quick glance at a LinkedIn profile or a company’s "About Us" page. It involves mapping out the prospect’s industry landscape, understanding their specific financial pressures, and anticipating the ripple effects that a new solution might have on their various departments. When you enter a room already knowing the language of their business and the nuances of their competitive threats, the dynamic shifts. You move from being a salesperson looking for a commission to a consultant looking for a solution. For a complex sale, the "process" is often a maze of hidden stakeholders and technical requirements. Being prepared means you have already identified the likely objections from IT, the potential pushback from Finance, and the specific KPIs that the C-suite is actually measured on. If you wait until the middle of the call to discover these variables, you’ve already lost the momentum. Precision in your questioning—driven by the research you did before the call even started—allows you to cut through the surface-level small talk and get to the core of the business problem. Ultimately, the depth of your pre-call work dictates your ability to control the room. It gives you the confidence to challenge the prospect’s assumptions and lead the conversation toward a strategic outcome rather than a price negotiation. In the world of high-value contracts, the rep who is the most prepared is almost always the one who is viewed as the most capable of handling the client's future.

Many believe that the pivotal moment in customer acquisition is when they sign up or request a trial/demo. However, the reality is far more nuanced. Think back to the last time you subscribed to something only to cancel after the free trial. The journey from prospect to long-term customer is a process that requires a well-crafted customer success plan. So, what's the secret sauce to closing more deals? It all starts with the often-overlooked step: the pre-discovery call. In my experience developing demand generation and growth strategies for early-stage startups, I've noticed a common pitfall: the lack of a comprehensive sales strategy, particularly around the crucial discovery phase. Many founders lack sales experience, leading to missed opportunities. Whether you're a founder seeking to enhance your sales skills or aiming to refine your team's approach, preparation is key. Before diving into a call, thorough research is essential. Rushing into meetings without adequate preparation can result in low conversion rates. Simply put, booking meetings is not enough; converting them into lasting partnerships requires a strategic approach. Here's a checklist to guide your pre-call research: ➡ Company: ✅ Number of employees ✅ Industry ✅ Location ✅ Company name ✅ Overview of products/services ➡ Person: ✅ Name ✅ Role ✅ LinkedIn profile review ➡ Key Insights ("AHA Sparks"): ✅ Recent news about the company ✅ Knowledge of competitors ✅ Industry trends affecting the prospect ➡ Client Hypothesis: ✅ Presentation triggers ✅ Desired product benefits ✅ Potential objections ✅ Decision-making stakeholders Armed with this information, you can position yourself as an expert and tailor your approach to the prospect's specific needs. Let's illustrate the impact of thorough research with a scenario: Generic Sales Rep: What are your objectives for this quarter? Prospect: Well, we're aiming for over 70% growth. Generic Sales Rep: Interesting. How do you currently manage your data? Now, compare that with a prepared approach: Prepared Sales Rep: "Congratulations on your recent funding! With your ambitious growth plans, I'm curious to learn more about your objectives for the upcoming quarter." Prospect: Thank you! We're looking to acquire Acme to bolster our product and expand into new markets, aiming for 74% growth and initiating A/B testing by month's end. Prepared Sales Rep: Impressive strategy. As a marketing director, I imagine data management is crucial. How do you plan to tackle that? Notice the difference? By demonstrating genuine interest and insight, you build trust and credibility, setting the stage for meaningful conversations and, ultimately, successful partnerships. In today's competitive landscape, the ability to differentiate yourself through personalized engagement is paramount. So, before your next call, remember: the key to unlocking opportunities lies in the preparation.

When I ask prospects how they prepare for their upcoming sales call, they often look at me funny and say, "well, I plan to go sell them." Yikes. If I ask my next pilot about his preparation for my next flight, I hope he doesn't say, "well, I plan to fly the plane." Or my surgeon saying, "I'll figure it out when I get in there," before an operation on me! Preparation is the mark of professionalism in EVERY industry. A lack of preparation will lead to an increase in chaos. And in sales, chaos means deals getting pushed to the next month or next quarter, frustration for both prospect and seller and many missed opportunities. If you want to be well-prepared before your next sales call, here are a few of the questions you need to answer: 1) Why does the prospect think you are meeting? 2) What are some general industry trends that may be impacting your prospect? 3) What are some problems they told you they were facing on your initial phone call? 4) What are some questions you must ask to better understand their opinions about their current situation 5) Where could you screw this up? 6) What is your biggest fear that you need to share with your prospect at the beginning of the sales call? There are more questions, of course, but this is a good start. Take 5 minutes after you set the appointment and answer these questions thoughtfully. I guarantee you'll find yourself in a much better position before AND after you meet with your prospect than if you hadn't.

Founders and sales reps — most think they are much better at selling than they actually are. So they get lazy and do not prepare properly for their sales calls — which is hurtful to both their career and businesses. If you’re not on your toes, someone else will be. In my case, I have no idea how many sales meetings I’ve done in my career — but it’s definitely in the thousands. With that experience, you would think that I could just show up and pull off a brilliant performance, right? Sometimes I might, but I’m not going to leave it to chance. Which means I’ve never prepared myself better for important meetings than I do today. Yet, it seems completely foreign to most sellers I come across. When asked, they say: “I prepare by visiting their website and LinkedIn profile and having a demo/presentation ready.” That is what I would call the BARE minimum of preparation for a sales call. Preparation is not whatever information you can retrieve 5 minutes before the call. Great preparation contains: - Industry research (market, trends, problems) - Company research (product, audience, competitors) - Hypothesis creation (problems, consequences, personal impact, business impact) - Meeting structure and questions (perspective, situation, problem, consequence) You can’t do it in 5 minutes — but over time, you might be able to do it in 30. Yesterday, I had a short call with an inbound lead. Their final remarks? “We’ve already learned a lot just by experiencing how you approached this

Every GTM miss I’ve seen starts the same way: A TAM slide that looks great in the board deck… but breaks the moment it hits the field. We’ve heard it dozens of times from early-stage founders: “Our TAM is $20B, we can sell to all SaaS companies, 50–500 employees.” In reality: silence, long cycles, and deals that never quite get to commit. Here’s how we fix that at Leadle, so that the “wishful ICP” becomes a list of buyers who actually pay. How we reconcile TAM with reality:  1. Start with the ‘wishful ICP’. We write it down clearly: industry, size, roles, use case. This is the story you want to be true. 2. Pull reality from the CRM. We look at the last 12–18 months of deals in CRM - wins, losses, no-decisions. Who actually paid? Who never moved? It usually doesn’t match the story above. 3. Enrich everything. Every account and contact goes through Clay - funding stage, team size, hiring, tech stack, geography. Now the “slide TAM” becomes an actual account list with context. 4. Score segments by what matters. Not all ICPs are equal. We measure: → Meetings per 100 accounts → Win rate → Deal size → Cycle length The top segments become “go-to” cohorts. The rest? We drop them. 5. Run plays in cohorts. Each cohort gets its own brief: who we’re targeting, the triggers to watch, and the opener that’s resonating. The scored accounts are synced back into Pipedrive → Clay signals → Smartlead/HeyReach workflows. That way, the team isn’t just blasting - they’re connecting at the right moment. ✅What changes when you do this → TAM shrinks (good), focus sharpens (better), pipeline moves (best). → Messaging stops being generic. because you’re speaking from real patterns you’ve seen. → Planning gets clearer: you know which 500 accounts to work this month and why. Every time we see GTM go sideways, it’s rarely because of the channel. The problem is higher up, at the strategy level. When you fix your TAM, you have a >50% chance of fixing your GTM.

Reflection: I recently spoke with a buddy who was frustrated after losing a big deal. “We just got unlucky,” he said. But was it really luck? Hmmmm [... and perhaps he should be working with a sales coach that supports bigger deals... just sayin'] Often, what feels like “bad luck” in sales is really about preparation. Or, in this case, the lack of it, the absence of a solid pre-call plan, even though I've told this buddy repeatedly about pre-call planning. In my experience, sales teams that model repeatable and predictable success have high accountability around pre-call planning. Successful deals are built from successful meetings that have foundations built long before the meetings start. - researching the client - predicting buyer personas - understanding their pain points - preparing value-driven questions - anticipating objections Explorer Roald Amundsen said, “Victory awaits those with everything in order. Luck, people call it. Defeat is certain for those who neglect to take the necessary precautions in time; this is called bad luck.” But I've seen so many sellers resist pre-call planning... Me too btw.. until I lost too many deals. ⏰ feeling “too busy” to prepare 🤪 overconfidence from past wins 🤷♂️ misunderstanding the value of planning 🥷 a desire for quick action over quality preparation 🤯 fear of exposing skills gaps (ego) ... and their leaders underserve them by making it optional. A well-prepared seller isn’t “lucky” - they’re ready to win. Building a culture that values pre-call planning can be the difference between missed opportunities and closed deals. 🏆 Pre-call planning isn’t a luxury; it’s essential. Those who put in the effort to truly prepare will often seem “lucky” in their outcomes. So, the next time you have a high-stakes meeting, ask yourself: are you ready to win, or are you leaving it up to “luck”? #PreCallPlanning #Preparation #Luck #SalesSuccess - P.S. Are you looking to Scale your business, your impact, your results? We design the Building Blocks of Scale for hundreds of businesses: Vision & Offer - Leads - Sales Systems - Leadership - Talent Development P.P.S Comment "Send me a PCP" for a Pre-Call Planning Tool.

I used AI agents to solve market segmentation in a niche industry. The sales team at my new company was struggling with one main thing: Not having a reliable signal that a company was relevant for them or not. Can't blame them... finding sales signals in the energy space is, well, not a common thing. Tools like Clay, ZoomInfo, and Apollo are great for general B2B signals. But when you need signals that are deeply vertical, like: → Who's developing renewable projects in Europe? → What’s their role in those projects? → Where are their assets, and how large are they? ...there’s no out-of-the-box data provider that solves that. So I built something internally to help us fix that gap. Using Clay, I set up a multi-agent research workflow that: • Scrapes company websites + sitemap data • Uses agents (Claygent, EXA, Perplexity) to extract project-level info • Distills it into structured columns - tech type, project size, role, geography • Aggregates and verifies multiple research sources And with the results, we can now segment companies into our TAM / SAM / ICP The outcome powers: → Sales prospecting → Market expansion → Campaign planning No more asking AI "Is this company a good fit?' Instead: AI focuses on gathering data → we control of market segmentation: → TAM → SAM → ICP The principles apply in GTM Engineering: → Use AI to gather intel, not make judgments → Pick the few signals that will definitively segment your market → Build deterministic filters, not subjective scores Your market segmentation is your competitive advantage. Don't outsource the logic. Hope it's useful for other GTM people building in verticals with niche signals✌️

During our time at Spendesk, we went from 5% to 15% meeting booked rate without hiring a single SDR, thanks to a signal-based selling framework. Here's how this framework works: Step 1: TAM building You stop building lists. Signals automatically feed new ICP-fit accounts into your TAM in real time. A company raises a Series B, a new VP Sales joins a firm that matches your ICP. That account enters your system automatically. Step 2: Enrichment The moment a new account enters your TAM, an AI research agent fills every context gap automatically. Contact info, tech stack, company size, and recent news. The rep gets a fully loaded account record without touching a single tab. Step 3: Sales Readiness Scoring A single signal doesn't tell you much. The system stacks signals across every account in your TAM to build a Sales Readiness Score. A new hire triggered the account entering the system but an agent keeps monitoring: funding activity, job postings, website visits, intent data. High readiness goes into the rep's book of business. Medium readiness goes to the AI SDR. Step 4: Automated action The system routes the right play to the right person without manual input. Rep gets a Slack alert with full context. CRM is already updated. All they have to do is show up. Reps only touch accounts that are already ready. We ran this at Spendesk across 100+ reps. Meeting booked rate went from 5% to 15%. This is a different model entirely. ↓