Sales Gravy: Jeb Blount

• How to Build an Enterprise Sales Strategy for Startups (Ask Jeb)

  Here's a problem that'll tie you in knots: You've got a killer software solution that saves companies massive amounts of money on employee benefits. You know exactly who needs it: Fortune 1000 companies with self-insured health plans. But you can't get a single meeting with the people who matter. That's the situation Peter Kleinman from Provo, Utah, finds himself in. As the sales and marketing guy for his dad's startup, he's tasked with landing enterprise clients while juggling full-time classes at BYU. He has LinkedIn, Sales Navigator, and a burning desire to make it work. He also has virtually no chance of success using his current approach. If you're nodding your head right now, keep reading. Because Peter's problem is your problem if you're trying to sell into enterprise accounts without the business acumen, social proof, or strategy to break through. The 100-Foot Wall Problem Here's the biggest issue: Fortune 1000 CHROs and C-suite executives have built a wall around themselves that's about 100 feet high. Their entire job is keeping people like you from wasting their time. And if you're young, inexperienced, or new to enterprise sales? That wall might as well be 1,000 feet high. Peter is doing everything the sales books tell you to do. He's going straight to the top. He's messaging decision makers on LinkedIn. He's targeting the right titles. He's also getting absolutely nowhere. Here's why: It has nothing to do with age and everything to do with business acumen. You can't speak the language of enterprise buyers if you've never lived in their world. You don't understand their buying process, their risk aversion, or the organizational politics that determine whether your deal lives or dies. Most critically, you're trying to sell something they don't even know they need. And you have zero social proof to back up your claims. That's not a recipe for success. That's a recipe for frustration, burnout, and a pipeline full of nothing. The Bottom-Up, Top-Down Strategy If you can't get to the top, start at the bottom. I'm not talking about giving up on enterprise accounts. I'm talking about running a multi-threading strategy that builds your business acumen while creating pathways into those massive organizations. Here's how it works: Find the amplifiers. These are the people in the trenches who actually deal with the problem your solution solves every single day. They're not directors or VPs. They're managers, analysts, and coordinators who feel the pain but lack the authority to fix it. These people are 100 times easier to talk to than C-suite executives. They'll take your call. They'll teach you. They'll tell you exactly what's broken in their organization and how decisions actually get made. Compress your experience. When you talk to these amplifiers, you're not selling. You're learning. You're asking questions like, "Help me understand how you make these decisions," and "What problems are you running into?" Every conversation compresses years of experience into hours. You learn the language. You understand the pain points. You gather insights that become ammunition for conversations with decision-makers. Surface the insights upward. Now when you finally get in front of that CHRO or VP of Benefits, you're not some kid with a PowerPoint. You're someone who understands their organization better than they do. You can tell them stories about what their own people are experiencing and how you can close the gap. That's how you get meetings. That's how you build credibility. That's how you win deals when you have no business acumen and no social proof. The Insurance Broker Shortcut Here's another path Peter needs to explore: Insurance brokers. If you can't talk to the self-insured companies directly, talk to the people who advise them. Insurance brokers work with these organizations every day. They understand the buying process. They know the pain points. They're infinitely more accessible than Fortun...

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• How to Turn the Panic Button into a Profit Engine

  The year was 1938. Families across America gathered, listening during the golden age of radio. On the eve of Halloween, a broadcast interrupted their evening: A live report claimed Martian cylinders had landed in Grovers Mill, New Jersey. Within minutes, panic erupted as citizens fled their homes, convinced Earth was under alien attack. The entire event was fake. It was a perfectly executed radio drama by 23-year-old Orson Welles. Here's the sales lesson tucked into The War of the Worlds sci-fi scare: Welles wasn’t just reading a script. He was executing a masterful lesson in emotional engagement. He had listeners hooked, buying into his story emotionally before their brains had time to register, "Wait, this can't be real."  That emotional buy-in is a core tenet of sales: People buy on emotion and then justify it with logic and facts. If rational adults can flee their homes over a fictional Martian invasion, imagine the force of emotion you can unleash when you find your prospect's emotional trigger. Sharpen your emotional intelligence, and you deploy a powerful sales tool. Emotion Gets the Attention, Data Seals the Deal Welles sold tension, uncertainty, and gravity, not a product. His voice was calm yet urgent, delivered with the authority of a trusted news anchor. The audience felt an adrenaline surge—heartbeats rising, eyes widening—before they had time to check the facts. This is the non-negotiable first step in sales. Your passionate storytelling creates the emotional charge. Your tone carries more weight than any spreadsheet full of ROI data. Emotion gets your buyer leaning in and invested in the outcome. The data you provide simply helps them sleep well at night after they’ve already made their decision. If your message isn't landing, stop reviewing your product deck and start analyzing your delivery. Are you speaking with urgency, and are you connecting to their emotional state? Without that emotional resonance, even the best solution just adds to the noise. Authority Isn't Arrogance, It's Command Welles dressed his fictional story in familiar trappings like live news bulletins, eyewitness reports, and crackling radio static. Each detail made the unbelievable feel legitimate. He commanded belief by establishing immediate, undeniable authority. Bring that same presence to your sales interactions. Authority isn’t arrogance; it’s commanding belief. Sound like someone who’s been there, knows the terrain, and has the solution. Communicate with unwavering authority, and you build trust before price discussions begin. This is how you sell the experience. Prospects must believe in you and your company; belief in your product comes next. They buy the experience of working with you before seeing the product. If you sound uncertain, you’ll never build a foundation of trust. Stay Steady to Control the Chaos Welles predicted a strong reaction to his broadcast and stayed calm, controlled the narrative, and guided the audience through the panic he was creating. In sales, moments of crisis or uncertainty test your professionalism. When a prospect goes cold, objections arise, or a competitor attacks, do not panic. Do not mirror their anxiety—it only feeds chaos and cedes control of the deal. Control the process, control yourself, control the outcome. When deals wobble and emotions spike in your buyer, that is your moment to shine. Breathe, slow down, ask questions, and lead steadily. Be the calm voice that reassures, guides, and inspires confidence. Mastering internal composure is the essence of emotional intelligence in sales.  Your Action Plan: Develop Your Sales EQ Mastering composure under pressure is a skill, not a gift. It requires commitment to developing emotional intelligence so you can use logic while others react in fear. Start a 'Rejection Journal' Drill. Stop letting rejection or setbacks paralyze you. Create a Failure Log to immediately document your feelings (frustration,

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• The Sales Skills That Matter Most When AI Handles Everything Else

  AI in sales isn't coming soon. It's already here, and it's quietly separating the salespeople who will thrive from those who won't. On the Sales Gravy Podcast, sales expert and author Victor Antonio shares this quote: "You won't lose your job to AI. You'll lose your job to people who are using AI."  While everyone debates whether artificial intelligence will replace salespeople, the real shift is already happening. What you need to know is which parts of your job will still matter when a machine can do everything else. The Trust Formula Still Requires Humans Most people think AI in sales is about automation. It's not. It's about augmentation. Yes, AI can write your emails. It can analyze your pipeline. It can schedule your meetings and generate your proposals. But it can’t build trust with a buyer who's about to make a six-figure decision they're terrified of getting wrong. Trust in selling comes down to three things: Understanding the buyer’s point of view Demonstrating real expertise Keeping the buyer’s best interest front and center When a buyer is staring at a purchase order that could make or break their business, they don't want a chatbot. They want a human being who says, "I've got you. This is the right move." Simple Sales No Longer Require a Sales Rep  Transactional jobs are disappearing. AI sales agents can already handle simple sales from start to finish. A customer calls about a broken window seal. The AI analyzes the image, checks inventory, schedules a technician, verifies the warranty, and puts the appointment on the calendar. No human required. This isn't science fiction. These systems exist today. AI handles simple tasks easily, but complex sales still require humans. Everything on the straightforward end—cold outreach, basic prospecting, routine follow-ups—is getting automated fast. But complex B2B sales are different. When deals involve multiple stakeholders, custom solutions, and high-stakes decisions, buyers still need salespeople. Humans don't trust machines with decisions that keep them up at night. Your job security lives in complexity. If you're selling simple products with simple processes, you need to start adding value now.  What You Should Be Doing Right Now Most salespeople are waiting while AI transforms the industry. Don’t make that mistake. Here’s how to start experimenting with AI today: Use ChatGPT, Google's Notebook LM, or your AI of choice to digest long articles and research reports in minutes instead of hours. Feed it information about your products and competitors to create your own custom knowledge base. Role-play objection handling by assigning it different buyer personas and practicing your responses. Ask it to critique your proposals before you send them to catch weak points you might miss. These tools aren't perfect. They'll feel clunky at first. But you're not trying to master AI today. You're building comfort with technology that will be 100 times more powerful in just a few years. The salespeople who are experimenting now will be the ones who know how to use AI when it really matters. The ones waiting for their leaders to force them to adopt AI will scramble to catch up. The Skills That Survive AI So what actually matters when AI handles the busywork? The biggest obstacle in complex sales isn't convincing buyers that your solution works. It's helping them trust their own judgment enough to decide. Buyers freeze not because of your pitch, but because of fear: What if I’m wrong? AI can show data, ROI models, and comparison charts—but building buyer confidence still requires human judgment. That's the skill that matters: Building buyer confidence. You need to get exceptional at reading hesitation—when a buyer goes quiet or starts asking the same questions in different ways. They’re not confused about your product. They’re uncertain about themselves.

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• How to Scale a $300K Company to Multi-Million Dollar Revenue (Ask Jeb)

  Here's a question that'll keep you up at night: How do you take a company from $300K in annual revenue to $1.5 million in 18 months, then scale to $3-$5 million within five years? That's the challenge facing Greg Hirschi from Colorado. He's the new executive leader of an 18-year-old company selling ethics assessment services to professional licensing boards. They've expanded from an entrepreneurial model to a small team with one salesperson and one customer service representative. The goal is aggressive growth, and Greg needs to know where to focus his limited resources to get the biggest bang for his buck. If you're nodding your head right now because you're in a similar situation, pay attention. Because the mistakes you make at $300K will haunt you at $3 million. The Resource Reality Check Let's be brutally honest about what a $300K revenue company means: You have no money. You have a razor-thin budget. You have one salesperson and one leader trying to do everything. At this stage, you have exactly one priority: REVENUE. You don't have the luxury of fixing operations, perfecting your tech stack, or building elaborate systems. You need to sell. Period. Here's where most small companies screw this up. They think selling means taking anything with a pulse. If it can fog a mirror, they'll do business with it. That's a death spiral disguised as growth. The Operator's Dilemma Greg comes from an operations background. He's analytical, process-driven, and systematic. Those traits are incredible assets for building a business, especially when the goal is to scale fast. But they can also be a liability when managing salespeople. Here's what happens: Operators think in systems and logic. Salespeople think in relationships and emotion. Operators want everything organized and predictable. Salespeople throw deals on the table that are messy and unpredictable. If you're an operator trying to lead sales, you need to understand this fundamental tension. Your salesperson is out there getting hammered with objections every single day, building narratives in their head about why people won't buy. You're thinking, "Just brush it off and do it again. What's wrong with you?" They're thinking, "You have no idea what it's like out here." This is why reading New Sales Simplified by Mike Weinberg is non-negotiable if you're an operator managing sales. You need to learn how salespeople think, how they operate, and how to lead them effectively without losing your mind. Start With Your ICP or Die Trying The single most important thing Greg needs to do right now to scale is get laser-focused on his Ideal Customer Profile. Not kind of focused. Not "we have a general idea." I mean obsessively, precisely, ridiculously dialed in on exactly who they should be targeting. Why does this matters so much at $300K? Greg's salesperson has a $600K pipeline and will close 50% of it. Sounds great, right? But if half those customers churn because they're the wrong fit, requiring constant re-education and hand-holding, Greg's salesperson will get stuck in account management mode. They'll stop prospecting for new business because they're too busy re-selling existing accounts. That's how you stay stuck at $300K forever. Your ICP drives everything. It determines your messaging, your marketing, your presentation materials, and which stakeholders you need to reach inside target organizations. It helps you build relevant social proof stories. It allows you to coach your salesperson on handling specific objections instead of generic brush-offs. Most importantly, it gives you guardrails. You can ask your salesperson in pipeline reviews: "Tell me the strategic reason why we should chase this account. How does it fit our ICP? Why is this worth our limited resources when our singular goal right now is growth?" When you're running a $300K company with one salesperson and one leader, you cannot afford to chase every deal.

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• What Surprises Salespeople the Most When They Pick Up the Phone (Money Monday)

  I've been intrigued by all of the LinkedIn posts lately from sales professionals, leaders, and experts proclaiming the phone is back! Even the “phone-is-dead” evangelists seem to have had a change of heart and are encouraging salespeople to “phone a customer.”  My favorite posts are from salespeople who took this advice, called a customer, and were surprised—even stunned—to discover that their customer actually wanted to talk. It’s more proof that buyers are starving for real, authentic, human-to-human conversations with their sales reps and account managers.  When Sellers Make Their First Call in Years I saw one post yesterday from an account manager who said that, for the first time in years, he had picked up the phone and called a customer. In his post, he described how rewarding it was to have a real, live conversation—as if this was some new revelation. He said that even though the phone was “old school,” he had given it a try because his customers weren’t responding to his emails anymore.  Although I'm super pleased to see that salespeople are rediscovering the power of the humble phone, I was bothered by this particular post because it is an indictment of just how far the sales profession has fallen over the past few years. It also exposes the malpractice of this guy’s leadership team. Seriously, how is it possible that his leaders and company allowed him to avoid having actual conversations with his customers for years?  Pick Up the Phone and Talk to Your Customers Account managers who are not talking with their customers, the ones who keep their customers at digital arm's length and send random “just checking in emails,” are swinging the door open and inviting competitors in. When you fail to proactively manage relationships—when you don’t talk with your customers—those customers end up talking to your competitors and considering other options. Nearly 70 percent of customers are lost due to neglect. Not prices, not products, not the economy, not aggressive competitors. Neglect! They feel the sting of being taken for granted. If you've ever been taken for granted (and I bet you have), you know that it makes you feel unimportant, small, and resentful, which can lead to the feeling of contempt. Resentment and contempt are the two most powerful negative emotions in the pantheon of human emotions. They are the gangrene of relationships, festering below the surface, slowly rotting away the connections that bind people together until the relationship is destroyed. The good news is the secret to defending accounts is completely in your control. It’s simple. Pay attention to your customers. And guess what? A simple, regular phone call can make all the difference. Just pick up the phone, dial their number, and ask or say: How are you doing? What can I do to help you? I have an idea for you.   Have a great weekend. Thank you for your business. Regular telephone contact ensures that you are top of mind with customers. Hearing your voice lets them know that you care. It doesn’t need to be anything particularly special. You don’t need to schedule it on their calendar. You don’t need a reason to tell your customers that you appreciate them.  Pick up the phone and say “hello” because it doesn’t cost a thing to pay attention to your customers. A “How AI Will Replace You” Reality Check But it’s not just that account manager and his company. Rather than picking up the phone and talking with people, sales professionals everywhere have replaced this beautiful, synchronous sales communication tool with email. This aversion to talking with people by phone has become so acute that at least half of Sales Gravy’s training and consulting engagements have focused on one thing: Teaching and compelling salespeople to pick up the damn phone and just have real-time human conversations.  So, let’s start with a reality check: The telephone is not old school.

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