Episodios

  • Stop Chasing Pipeline Multipliers: The Science of Building Clean a Sales Pipeline
    Jun 10 2025
    Here's a question that exposes one of the most dangerous myths in modern sales: How do you set the right pipeline creation target to consistently hit quota? That's exactly what Maryellen Soriano from New Jersey asked when she called into Ask Jeb. After crushing 134% of quota in her first year selling EdTech solutions—transitioning from owning her own childcare center to selling back into that same industry—she was being told she needed 11X pipeline to maintain her success. If that number made you cringe, you're not alone. The obsession with pipeline multipliers is creating more problems than it's solving, and it's time we had an honest conversation about what actually drives predictable revenue. The Pipeline Myth That's Killing Your Forecast Most sales teams are drowning in fake pipeline, and it's destroying their ability to forecast accurately. Leadership teams, especially in tech companies, consistently miss their numbers quarter after quarter because they're obsessed with one question: "How much pipeline do we have?" The real question should be: "How clean is our pipeline?" Would you rather have 11X pipeline filled with lottery tickets, or 2X pipeline packed with qualified buyers? The answer should be obvious, but somehow we keep chasing vanity metrics instead of focusing on what actually converts. Here's the brutal truth: All pipeline opportunities are not equal. Two Approaches to Pipeline Creation There are two ways to approach pipeline creation, and only one of them actually works consistently. Approach #1: Maximum Daily Prospecting (The Proven Method) Don't worry about how big your pipeline is. Worry about how much prospecting you're doing, and run on a daily cadence of prospecting that maxes out the time you can spend every single day. Prospect every day, every day, every day. I have a block of time every morning for prospecting. Then I'm prospecting during any gap during the day. If there's time between meetings, I'm doing outreach. Every single day I'm prospecting to the very max that I have time to prospect. When you do this, you don't have to worry about pipeline size because it takes care of itself. You never get into the desperation roller coaster because you never stop feeding the machine. Approach #2: Pipeline Multiplier Obsession (The Broken Method) This is where leadership teams fixate on having "5X pipeline" or "11X pipeline" because they think more is better. The problem? As soon as reps think they have "enough" pipeline, they quit prospecting. Then reality hits when half those opportunities were pipe dreams to begin with. The Science of Pipeline: The Law of Replacement If you want to look at pipeline like science rather than hope, you need to understand the Law of Replacement: You need to replace opportunities in your pipeline at a rate that is equal to or greater than your closing ratio. Let me give you a real example of how this works. In a previous role, I had my numbers dialed in perfectly: I knew I needed 10 first-time appointments every week About 50% would move to follow-up appointments (5 deals) I'd close about 20% of those follow-ups (1 deal per week) It took me about 20 prospecting touches to generate 2 first-time appointments Working backwards from one closed deal per week, I knew exactly what I needed to produce in terms of prospecting activity and first-time appointments to feed my pipeline consistently. If I didn't replace the deals that fell out every single week, I'd eventually end up with nothing. What Makes a Real Pipeline Opportunity Here's where most organizations get it completely wrong. They're stuffing their CRM with anything that moves and calling it "pipeline." A real pipeline opportunity requires a conversation. Not a form fill. Not a marketing lead. Not something someone else talked to and dumped in your CRM. You need to have qualified it yourself and made a decision that it belongs in your pipeline.
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    22 m
  • Top Sales Pros Know When to Exit Bad Deals (Money Monday)
    Jun 9 2025
    Have you ever been working on a deal where you had this feeling, this intuition, this Spidey sense – something in the back of your mind telling you that this wasn't going to close? That you were going to waste your time? Maybe you had one of the stakeholders who was against you – an enemy. There was a naysayer who kept calling you out. Maybe the stakeholders weren't engaged, or the incumbent vendor was so integrated into the organization that it was going to be very difficult to displace them. Whatever the case, you knew in the back of your mind that you weren't going to close the deal. But you kept working on it anyway. You rode that puppy to the ocean floor like the Titanic that it was. If you’ve done this, and I know you have, take heart because we've all been there. We've all had these situations, and we've later regretted them. Top Sales Pros are Quick to Walk Away From Bad Deals One of the traits of ultra-high performers that has always been true is that they're very quick to walk away from a deal they can't close – a deal where they've come to the conclusion that the probability of winning is so low it doesn't meet their threshold. The reason ultra-performers walk away from deals like this is simple: They know that the greatest waste of their time is investing it with the wrong prospect. The time they invest in a prospect that's not going to close is money down the drain, because it's time they can't focus on a deal that will close. But average salespeople? They hang on - hoping against hope that somehow, miraculously, things will turn around. In sales, awareness matters. You must always know where the exit is. There are two primary reasons why salespeople work on deals that are never going to close. Understanding these reasons is the first step to avoiding the trap. Reason #1: Is the Failure to Qualify Properly Too often, qualifying is treated like a one-and-done activity. We qualify the opportunity against our ICP. We qualify the numbers, budget, timing, urgency, and whether we're talking to a decision maker with buying authority. These are all quantifiable metrics that we can measure and check off our list. But ultra-performers take qualifying to the next level. Rather than treating it as a one-and-done activity, they understand that qualifying is never done. It's an ongoing process of awareness that keeps you tethered to reality in every deal. And their top qualifier, once they've checked off the must-haves, is engagement. Are the stakeholders engaged? Are the leaning in? Matching your effort, leaning in, answering questions, and working collaboratively with you? It's okay that there are some stakeholders who may be naysayers. That's normal in complex deals. But if you've got stakeholders who are enemies – people who are actively working against you – then your deal might be a bridge to far. Engagement is my number one qualifier. I'm constantly asking questions and giving stakeholders things to do to see whether or not they're engaged. If they're not engaged, I walk away because lack of engagement is a clear signal that you are not going to close the deal. Reason #2: An Empty Pipeline This brings us to the second reason salespeople stay in bad deals – desperation born from an empty pipeline. On Friday, Dennis J. Walker, who is a benefits consultant with USI, posted something on LinkedIn that perfectly captures this dynamic. Here's exactly what he wrote: Jeb Blount regularly states that you can't be delusional about your pipe, your prospects, your efforts, etc and be successful as a salesperson. This week one of the larger deals in my pipe definitely didn't progress the way I wanted- and it turns out one of the executives is what I call a "deal enemy" - he was actively working against me and my team. The last two meetings I've had with him tipped me off this could be the case; this week we had an incident that indicated he was actively working against ...
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    9 m
  • 5 Ways to Sell More by Uniting Sales and Marketing
    Jun 5 2025
    Your sales team just closed a $50K deal. Marketing takes credit because the prospect downloaded three whitepapers. Sales takes credit because they nurtured the relationship for six months. Meanwhile, you're wondering why this kind of success feels so random—and why similar prospects are slipping away. Companies with misaligned sales and marketing teams waste more leads and see annual revenue decline. But businesses that achieve true alignment? They close more deals and grow revenue faster year-over-year. The difference isn't talent, budget, or market conditions. It's whether your marketing and sales teams are pulling in the same direction or accidentally sabotaging each other. Clashing Departments Can Crash Your Bottom Line The consequences of misalignment between sales and marketing are significant. One common side effect is sales teams complaining about the quality of leads generated by marketing, often dismissing them as "bad leads." Another issue is messaging. Marketing can be blind to the value propositions that are working for sales if they do not understand the sellers’ pitches and approach to closing deals. Their messaging is stale and ineffectual, completely disconnected from where sellers are finding success. When marketing and sales have different metrics or goals, it leads to a breakdown in communication and a lack of shared understanding. That misalignment hampers productivity, damaging morale and impacting your bottom line. Start With the Customer Journey The most important aspect that sales and marketing need to align on is the customer journey. This involves mapping out every touchpoint—from initial awareness to final purchase to customer retention. Map the customer journey together—then act on it. This shared blueprint reveals exactly when prospects are ready for direct outreach versus when they need more nurturing. The payoff is immediate: Marketing delivers leads at peak readiness, while sales focuses their time on prospects most likely to convert. When both teams operate from the same customer journey map, handoffs become seamless and conversion rates climb. Tackle Sales Objections Together Every sales professional understands that the path to a closed deal is rarely a straight line. It's often a zig-zag through questions, doubts, and hesitations from prospects. Marketing’s role is to help develop messaging and collateral assets that help the sales team deal with these objections. This includes essential resources like case studies, white papers, product demonstrations, and ROI calculators. With the support of marketing materials, sellers have the resources to back up their pitch, highlight benefits, and keep buyers engaged. Most teams fail to communicate. Marketing creates polished but generic materials that sales doesn’t know exist. Sales knows which objections are the hardest to overcome but doesn’t have specific collateral to counter them. The winning approach: Sales documents the top 5 objections that derail deals, complete with context about when and why they surface. Marketing then builds laser-focused tools to address these concerns. Think comparison sheets for "your competitor is cheaper," implementation timelines for "this seems too complex," or peer testimonials for "we're not sure this works in our industry." Close the loop: Sales reports back on which materials move deals forward and which fall flat. Marketing iterates based on real-world results. This feedback cycle shifts objection-handling from guesswork into a refined system that consistently converts hesitation into confidence. Get Sales and Marketing Aligned Now How can businesses foster a stronger cohesion between sales and marketing? Here are six key strategies: Establish Shared Goals and Metrics Sales and marketing should work together to define common objectives and key performance indicators (KPIs). Action item: Schedule a joint planning session within the next 2 weeks to agree on 3-5 ...
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    27 m
  • Why Talk Time is the Worst KPI for Measuring Sales Performance (Ask Jeb)
    Jun 4 2025
    Here's a question that'll make your head spin: What do you do when your top performer is crushing quota but not hitting a required talk time KPI? That's question posed by Josh Robich and Josh Nelson from Nashville. Josh Nelson ranked 18th out of 130 reps in his first full year at a new company, but he was consistently falling short of the company's sacred talk time metric of three hours per day, averaging only 2.5 hours instead. Meanwhile, his company is obsessed with using talk time as their primary KPI to measure sales effectiveness. If you're shaking your head right now, you're not alone. Obsessing over the talk time KPI rather than actual sales outcomes is one of the most backwards approaches to sales management I see today, and it's costing companies their best talent. The Moneyball Problem: When Metrics Become Religion Remember the movie Moneyball? Billy Beane revolutionized baseball by focusing on on-base percentage instead of traditional stats that looked impressive but didn't correlate with winning games. He found a metric that predicted success. Talk time is the opposite of Moneyball. It's a vanity metric that makes leaders feel like they're managing performance when all they are really doing is measuring noise. Here's the brutal truth: Talk time means absolutely nothing if it doesn't drive revenue. It means nothing is the conversations are shallow, non-productive, or a poor buying experience. You can have reps talking for four hours a day who are dead last on your ranking report, while someone like Josh is closing deals left and right with only 2.5 hours of phone time. Which one would you rather have on your team? Why Talk Time Is a Lazy Leader's Crutch The reason companies fixate on vanity metrics like talk time is because it's easy. It requires zero investment in actual coaching, observation, or skill development. Think about it: It's much easier to look at a dashboard and say, "You need to talk more," than it is to actually listen to calls, analyze technique, and provide meaningful feedback on discovery questions, objection handling, or closing skills. But here's what happens when you manage this way: You drive away your best performers and enable your worst ones. Your top performers get frustrated because they're being penalized for efficiency. Your bottom performers get comfortable because they can hit their talk time numbers while producing nothing of value. What Actually Matters: KPIs That Move the Needle Instead of obsessing over how long reps are talking, and other vanity KPIs, smart sales leaders focus on outcome-driven metrics that actually correlate with sales performance and closing deals. First-Time Appointments How many new conversations is each rep having? In sales, FTAs are your Money Ball. If a rep isn’t setting enough first-time appointments, they are sub-optimizing their sales potential. Next Step Conversion Rates What percentage of first-time appointments convert to second appointments? This tells you everything about relationship building, discovery skills, and value articulation. If Josh is converting at a higher rate with less talk time, he's simply more effective per conversation. Show Rates How many scheduled appointments actually happen? This reveals qualification skills, the ability to create urgency and commitment, and the quality of prospecting conversations. Pipeline Velocity How quickly are deals moving through your sales process? This shows you who's truly building momentum versus just having long conversations that stall deals in the pipeline. Revenue Per Hour The ultimate sales efficiency KPI is who is generating the most revenue per hour of phone time. Stop Obsessing Over the KPI and Start Coaching When you shift your focus to outcome metrics, everything changes. Instead of telling reps to "talk more," you can provide specific, actionable coaching: For the rep who has great first-time appointment numbers but poor conversion rates...
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    15 m
  • In Field Sales Driving is Not an Accomplishment (Money Monday)
    Jun 2 2025
    If you are spending more time staring at your windshield instead of looking into their customers' eyes, you are doing field sales wrong. Over the past couple of years, there's been a resurgence in field sales. Businesses everywhere are adding field salespeople and sending reps out into the territory to meet with customers face-to-face. And for good reason – human beings buy from human beings. The most powerful way to anchor relationships, solve problems, and sell more is to actually get in front of your customers. With AI creating so much noise in the system, it's getting harder to prospect via email and social media. Going out and knocking on doors has become an easier way to connect with people, build relationships, and open up opportunities in your pipeline. And the good news, at least for now is that prospects are happy to see field sales pros and inviting them in. But with the resurgence of outside sales comes an age-old problem: Field salespeople have got to travel to get to customers. And here's the brutal reality – the single greatest waste of time for field sales professionals is staring at a windshield. On this Money Monday segment of the Sales Gravy Podcast I'm going to teach you exactly how to minimize windshield time and maximize face time. Because at the end of the day, you don't get paid to drive. You get paid to sell. The Windshield Time Delusion Too many reps delude themselves into believing that driving from one place to another is "working." Let's get something straight – driving is not an accomplishment. I don't care if you put 100 miles on your vehicle in a day. That doesn't mean you accomplished anything meaningful. It just means you drove from one place to the next, burning dinosaurs and wasting time. I see this all the time. Reps will drive to one customer, then drive all the way across their territory to another customer, instead of concentrating their work in a single geographical area. They'll dead-head out to an appointment, then drive all the way back to the office, passing up dozens of prospects they could have walked into along the way. Don’t confuse activity with productivity. They think because they drove all over creation, doesn’t mean you had a productive day. Your job is to be in front of customers, not behind a steering wheel. Every minute you spend staring at your windshield is a minute you're not building relationships, solving problems, putting new opportunities in the pipe or closing deals. The Mathematics of Effective Field Sales Territory Management Let me put this in perspective with some simple math that will blow your mind. Let's say you're a typical field sales rep working in a moderate-sized territory. You make five customer visits per day, and between poor route planning and territory management, you spend an average of 45 minutes driving between each appointment. That's 3 hours and 45 minutes of windshield time daily. Over a five-day work week, that's 18 hours and 45 minutes of non-productive driving time. That's nearly half of your work week spent accomplishing absolutely nothing. Now, let's say you tighten up your territory management and reduce that drive time to 20 minutes between appointments through better planning. You're now down to 1 hour and 40 minutes of windshield time daily, or 8 hours and 20 minutes weekly. You just freed up over 10 hours per week. That's enough time for 15-20 additional customer visits or prospect calls. Over a month, that's 60-80 more customer touchpoints. Over a year, that's 720-960 additional opportunities to build relationships and generate revenue. The reps who figure out how to minimize windshield time don't just have better work-life balance – they absolutely dominate their territories and blow past their quotas while their competitors are still driving around aimlessly. Map Your Territory Into Quadrants This is why the first rule of field sales is getting your territory mappe...
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    13 m
  • Why Top Sales Performers Use AI as Their Secret Weapon
    May 30 2025
    AI isn't here to replace you; it's here to boost your game. Used wisely, AI can be your secret weapon. AI is everywhere: in social selling, content creation, automation, to say the least. Here's the double-edged sword: If you're trying to outsource everything to AI, you won't last. If you're stuck in the old ways, refusing to adapt, you'll get left behind. Top performers are integrating AI into their workflows to make their human skills even sharper. They know AI is the edge they need to rise above the competition. Where AI Actually Delivers Value Think about how much sales time you burn on necessary tasks that don't drive revenue, like data entry and research. That's where AI shines. It handles the repetitive work faster and more accurately than you ever could. Feed it your ideal customer profile, and you can have a filtered list of prospects before you even finish your coffee. AI can analyze thousands of LinkedIn profiles in minutes to identify prospects who match your best customers' characteristics. It can scrape company websites, news articles, and financial reports to give you conversation starters that actually matter. While you're having one discovery call, AI can prep intel for your next five meetings. Consider email outreach. Instead of sending generic templates, AI can help personalize messages at scale using real company data—recent funding rounds, leadership changes, and industry challenges. All this results in open rates that don't make you cringe and response rates that actually justify your time investment. Be Smart About How You Integrate The mistake most sales reps make is thinking AI means "set it and forget it." That’s plain wrong. The winners are using AI as a research assistant, not a replacement for judgment. They're feeding it context, reviewing its output, and adding the human insight that turns data into deals. The best use AI to identify patterns in their closed-won deals, then apply those insights to current opportunities. They analyze which messaging resonates with different buyer personas, then craft more targeted outreach. They're not working harder; they're leveraging better intelligence. Take objection handling. AI can analyze your call recordings to identify the most common pushback you're getting, then help you develop stronger responses. It can even suggest which case studies or references would be most compelling for specific prospect types. It’s taking your experience and making it work for you at warp speed. What's Coming Next for AI Wait until you see what’s on the docket for AI advancements: AI agents that anticipate what you need before you even ask. What if your follow-up email was already drafted after a call, incorporating specific points from the conversation? Your proposal includes ROI calculations tailored to their business model, all generated from publicly available data about their company. AI will soon do more than respond to prompts; it will proactively support your sales process. It'll flag when a deal is stalling based on engagement patterns. It'll suggest the optimal time to follow up based on the prospect's communication preferences. It'll even coach you on your delivery by analyzing successful calls from top performers. That’s why the time to adopt is now. Don’t let AI’s growth outpace your own knowledge of how to use it. Stay on top of new systems and improvements. The Human Element Remains King But here's what AI will never recognize: the moment in a sale when a prospect's voice changes and you know they're really interested. It doesn’t have the ability to read between the lines of what someone isn't saying. It lacks the intuition that tells you to pivot your pitch mid-conversation because you've spotted a better angle. AI can't build genuine rapport. It can't adapt to the subtle cues that tell you someone's ready to buy or needs more nurturing. It can't handle the complex, nuanced objections that require empathy and creative...
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    1 h y 15 m
  • Strategies to Turn Your Windshield Time Into a Competitive Advantage (Ask Jeb)
    May 28 2025
    If you're in field sales, you know the reality: You spend hours every week sitting behind the windshield, staring at traffic that's moving at the speed of molasses. Whether you're dealing with Atlanta's notorious I-285 parking lot or any other major city's rush hour nightmare, that windshield time is either making you better or making you bitter. Recently on the Ask Jeb segment of the Sales Gravy podcast, Jacob Kimrey asked about helping his field sales team maximize their productivity while stuck in traffic. But here's the thing—this advice isn't just for managers to give their reps. It's for YOU, the field rep, to take control of your own success. Let me tell you how to turn those frustrating hours in traffic into your secret weapon. Driving Isn't an Accomplishment First, let's get something straight: Driving is not an accomplishment. I don't care if you put 200 miles on your car today—that doesn't mean you accomplished anything meaningful for your business. Too many field reps confuse activity with productivity. They think that because they drove all over creation, they had a productive day. Wrong. The goal is to minimize your windshield time and maximize your face-to-face time. But when you ARE stuck in traffic, you better make damn sure you're using that time to get better. Smart Territory Management Saves Windshield Time Before we talk about maximizing windshield time, let's talk about minimizing it through smart territory planning. Map your territory into quadrants: Monday territory, Tuesday territory, Wednesday territory, Thursday territory, and Friday territory. If you're supposed to be in your Monday quadrant but you're driving to your Friday area, you better have a damn good reason. When you're planning your field time: Group your appointments geographically: Don't hopscotch all over your territory in one day. Plan your route in advance: Use your CRM to map out the most efficient route. Use the T-calling technique: When you arrive somewhere for an appointment, look left, look right, look behind you—can you make additional calls in that immediate area? The tighter your route planning, the more selling time you create and the less windshield time you waste. Prospecting from the Road (Safely) Now, here's where it gets interesting. That windshield time can actually become prospecting time—if you do it safely and legally. There are apps and dialers that let you load phone numbers and dial hands-free while you're stuck in traffic. You can also set up your phone so contact numbers are easily accessible with voice commands. Safety first: Only do this when you're completely stopped in traffic or pulled over. Never compromise safety for a sales call. Hands-free follow-up calls: Use voice-to-text features to send follow-up messages to prospects or customers. Planning calls: Call ahead to confirm appointments or reschedule meetings. Customer check-ins: Those relationship-building calls that keep you top-of-mind with existing customers. The key is preparation. Have your call lists ready, know who you're calling and why, and keep it simple and safe. Voice Technology Is Your Friend Today's smartphones have incredible voice capabilities that field reps should be leveraging: Voice-to-text for quick CRM updates Voice memos to capture important thoughts or follow-up reminders Hands-free scheduling and calendar management Voice-activated research on prospects or companies Learn to use these tools, and you'll be amazed how much more productive your windshield time becomes. Welcome to Automobile University The number one thing you should be doing while stuck in traffic is attending what the great Zig Ziglar called "Automobile University." When you're sitting in your car, staring at brake lights, what's coming through your speakers? Is it the news (which will just make you angry)? Music (which won't make you any money)? Or are you investing in content that makes you be...
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    11 m
  • 3 Reasons Most Value Propositions Fail and What to Do About It
    May 23 2025
    Most value propositions stink. They’re boring, generic, feature-heavy garbage that make buyers’ eyes glaze over. And the worst part? Most salespeople don’t even realize their value proposition messaging is hurting them. On this week’s Sales Gravy Podcast, Lisa Dennis breaks down her process for building value propositions that actually work—the kind that grab buyers by the heart and don’t let go. But before we get to the solution, let’s talk about why most value propositions fail miserably. Reason #1: You’re Talking About Yourself, Not Them Here’s the fundamental problem with 90% of value propositions: They’re all about you. “We’re the industry leader with cutting-edge technology and award-winning customer service that delivers best-in-class solutions…” Blah, blah, blah. Do you hear that sound? That’s the sound of your prospect mentally checking out. Here’s a hard truth about human nature: Nobody cares about you. They care about themselves. Every buyer wants to talk about their problems, their challenges, their goals, and their pain points. When you launch into your pitch about incredible features and market-leading capabilities, your buyer is silently thinking, “What does this mean for me?” And if you don’t answer that question immediately, you’ve lost them. Your value proposition isn’t a corporate brochure. It’s not a marketing slick. It’s the value-bridge between what you do and what they need. If it’s a monologue about you, your company, and your product features you’ve lost the game before kickoff. What to do instead: Make your value proposition a laser-focused spotlight on them. Start with their problem, not your solution. Lead with their pain, not your product. Reason #2: You’re Using Generic, Meaningless Buzzwords Most value propositions include phrases like “industry leader,” “best-in-class,” “cutting-edge,” or “world-class customer service.” “We’re a one-stop shop with purpose-built solutions that increase efficiency and decrease costs.” Really? And I suppose your competitors specialize in decreasing efficiency and increasing costs? These phrases and buzzwords make you sound exactly like every other salesperson who’s ever walked through your prospect’s door: boring. Here’s the brutal truth: If your competitor could copy and paste your value proposition and use it for their company, it’s not a value proposition—it’s forgettable noise. What to do instead: Get specific. Use numbers. Use their language, not yours. Instead of “increase efficiency,” say “reduce your monthly reporting time from 40 hours to 4 hours.” Instead of “industry leader,” show them exactly how you’re different and why that difference matters to them. Reason #3: You Haven’t Done Your Homework Most salespeople build their value propositions standing in their own shoes rather than those of their buyers. If you don’t know what keeps your prospects awake at 3 AM, if you don’t understand their specific challenges, and if you haven’t talked to real customers about why they bought from you (or didn’t), then your value proposition is built on sand. Guesswork rather than research. What to do instead: Talk to three groups of people and gain insight through their lens. Your Lovers: These are your raving fans. What do they say about you when you’re not in the room? What specific problem did you solve that made them heroes in their organization? Your Likers: These are satisfied customers who aren’t writing love letters about you. What almost made them choose your competitor? What reservations did they have? Your Haters: These are the tough conversations. The prospects who chose someone else or the customers who fired you. Why? What did they feel you were missing? This insight helps you shape your messaging so that it connects with the buying motivators of potential customers. How to Build a Value Prop That Actually Works Now that we’ve covered why most value propositions fail,
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    48 m
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