Episodios

  • Stone Tablets, Trade Shows, and Telephones: 4,000 Years of Sales History

    Stone Tablets, Trade Shows, and Telephones: 4,000 Years of Sales History
    Feb 12 2026
    Imagine that you're so angry about a business deal gone wrong that you grab a chisel, find a slab of stone, and spend hours carving your complaint. That's exactly what a Mesopotamian merchant did in 1750 and made sales history. The merchant was furious because he'd been promised high-grade copper, but the final product was subpar. That angry customer complaint is now sitting in the British Museum, 4,000 years later. The tablet reads: "What do you take me for? That you treat someone like me with such contempt?" If you think dealing with issues in the sales process is a modern problem, you're off by about four millennia. Sales Hustle Is Ancient We talk about sales like it's a modern corporate invention. CRMs and automated sequences are new, but the art of the deal and dealing with angry customers? That’s been around since humans started trading. The copper merchant in 1750 BCE wasn't just selling copper. He was managing client expectations, handling logistics, and clearly failing at quality control. The core practices of B2B sales—promise, delivery, and relationship management—haven't changed. 1600s: Sales Becomes a Profession Fast forward to 1600, and you see the founding of the East India Trading Companies. They were some of the first corporations that allowed people to buy shares in a business. One of the East India Trading Companies was owned by "the 17 gentlemen"—a group of wealthy investors who funded global trade expeditions. They kept spices like nutmeg, pepper, and cinnamon flowing across continents. The spices were so valuable that they were practically currency. This was B2B sales at scale. Shareholders' expected returns. Merchants negotiated deals across continents. The stakes were massive, and so were the profits. This era established something critical to modern sellers: the separation between ownership and operation. The 17 gentlemen didn't sail the ships or negotiate every spice deal. They hired people to do it. Sales stopped being a personal trade and became a repeatable profession with accountability structures built in. 1851: Visibility and Competition Arrive The Great Exhibition in London in 1851 was the world's first massive B2B trade show in sales history. Thousands of exhibitors. Hundreds of thousands of attendees. A giant glass building called the Crystal Palace. Nearly 200 years later, sales pros still pack convention centers, set up booths, and fight to stand out in a sea of competitors. This is where B2B sales became visible. You weren't just competing against one or two local merchants anymore. You were standing next to dozens of alternatives, all promising similar value. Differentiation became mandatory. Following up meant writing a letter and waiting weeks for a response. Today, if you're not following up within 24 hours, you're losing to competitors who are. 1957: Reach and Leverage Scale Up The first inside sales team was formed at a company called Dial America in 1957. Before that, if you wanted to sell, you hit the road. Door-to-door, city-to-city, face-to-face. Every single deal required physical presence. The telephone changed everything. Suddenly, salespeople could work virtually, reach more prospects, and close deals without leaving the office. One seller could now have 20 conversations in a day instead of three. The math of sales productivity fundamentally shifted. Fast forward to today, and inside sales is the dominant model. The tools have evolved—Zoom calls, screen shares, digital demos—but the core principle remains: you don't need to be in the same room to build trust and close deals. From Stone Tablets to Instant Messages: Why Speed Matters Now Think about the effort that the merchant put into carving his complaint into stone. He didn't fire off a quick email. He didn't leave a one-star Google review. He created a permanent record that would outlive both him and the seller by thousands of years. Today, complaints are easy. Maybe too easy. A customer can blast you on LinkedIn, tank your review scores, or CC your entire executive team on an email thread—all before lunch. Every major shift in B2B sales increased speed. Trade shows multiplied visibility. Telephones let sellers reach 20 prospects a day instead of three. Email collapsed follow-up from weeks to hours. Social media made reputation instant and permanent. In 1750 BCE, you had time to respond. Now, you have hours—maybe minutes. Each acceleration rewarded the sellers who could execute fast without sacrificing quality. The ones who couldn't keep up disappeared. Why This Timeline Matters More Than You Think We’re in another massive shift in sales history. AI, automation, predictive analytics—the pace is relentless. It’s easy to think everything has changed. Zoom out 4,000 years, and the pattern emerges: speed accelerates, but the core practices stay the same. So the next time you get a harsh email from a customer, remember that stone tablet. You don’t have to worry about your ...
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    43 m
  • How Do You Stop Prospects From No-Showing Virtual Appointments (Ask Jeb)

    How Do You Stop Prospects From No-Showing Virtual Appointments (Ask Jeb)
    Feb 10 2026
    Here’s a question that’ll frustrate every salesperson reading this: What do you do when you prospect, set the meeting, block the time on your calendar, and then… your prospect no-shows? That’s the challenge Emily Weissmueller faces every single day. Emily is a former elementary school teacher who pivoted into K-12 edtech sales eleven years ago. She works with special education administrators, and like so many salespeople in 2026, her meetings are primarily virtual. She’s doing everything right: prospecting consistently, securing appointments, sending calendar invites. But when it’s time for the meeting? Hit or miss. Sometimes they show up. Sometimes she’s sitting there waiting while nobody logs on. If you’ve ever stared at a Zoom room alone wondering if your prospect forgot about you, you know exactly how this feels. And if you’re wondering whether confirmation emails help or hurt, you’re asking the wrong question entirely. The Virtual Meeting Paradox Let’s be honest about something: Virtual meetings are throwaway appointments for both sides. When you had to drive four hours to meet someone in person, both parties had serious skin in the game. You invested time, gas money, and effort. Your prospect blocked their calendar knowing you were making the trip. Neither of you would casually blow that off. But virtual meetings? They’re low commitment on both ends. No one’s driving anywhere. It’s just a calendar block that can easily get bumped by the next urgent thing that pops up. And when you’re selling into education like Emily is, where everything moves infinitely slow and decision-makers are incredibly risk-averse, you’ve got even more working against you. The question isn’t whether to send a confirmation email. The real question is: How do you stack the deck so heavily in your favor that prospects feel obligated to show up? The Commitment and Consistency Framework There’s a principle in human behavior called commitment and consistency. When people commit to something, they typically feel compelled to follow through. Otherwise, they feel guilty. And guilt is actually useful because you can leverage it to reschedule when someone doesn’t show. But the goal isn’t to make prospects feel guilty after they no-show. The goal is to engineer so many small commitments throughout the process that they show up in the first place. Here’s the system that works: Step 1: Confirm Verbally When You Set the Meeting When your prospect agrees to meet, always repeat it back: “Okay, so I’ve got you on Thursday, January 26th at 2:00 PM. Did I get that right?” When they say yes, that’s commitment number one. You’re putting it in their brain. You’re making it real. Then say this: “Let me grab your email and I’ll send you a meeting invite for your calendar just to make it convenient for you.” This does two things. First, it confirms you have the right email. Second, it gets another yes. That’s commitment number two. Step 2: Send a Meeting Invite That Actually Helps Most meeting invites are useless. They say “Meeting with Jeb Blount” or “Sales Call” and include seventeen different international dial-in numbers that nobody needs. Here’s what your meeting invite should look like: Title: Emily Weissmueller (Company Name) + Prospect Name (School Name) – Why We’re Meeting Location: Virtual Meeting (then paste the meeting link, nothing else) Notes: Keep it simple. Here’s the meeting link. If it’s a phone option, include just that number. Then add: “If anything changes, here’s my direct number and email.” When your prospect looks at their calendar the morning of the meeting and sees this, they know exactly who you are, why you’re meeting, and how to join. You own the moral high ground. Step 3: Send a Video (This Is Non-Negotiable) The next morning after you set the meeting, pull out your phone and record a 20-30 second video. Look at the camera. Smile. Sound excited. “Emily, this is Jeb at Sales Gravy. Thank you so much for agreeing to meet with me. I’m so excited to spend time learning about you and your mission for helping these kids. Just want to confirm our meeting is on January 26th at 2:00 PM. The invite is on your calendar. I can’t wait to see you.” Send that via email. Now think about what you’ve just done. You’ve made it personal. You’ve shown effort. You’ve demonstrated that you actually care about this conversation. It’s exponentially harder for them to no-show because they can see you’re a real human who invested time in this relationship. This philosophy is about going the extra mile to demonstrate that you’re different, that you care, and that this matters. Step 4: Leave a Voicemail the Day Before The afternoon before your meeting, when you know your prospect is likely gone for the day, call and leave a voicemail. “Hey Emily, this is Jeb. I’m so excited to meet with you tomorrow. I’ve been thinking about your ...
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  • Single-Contact Selling is Killing 34% of Your Deals (Money Monday)

    Single-Contact Selling is Killing 34% of Your Deals (Money Monday)
    Feb 8 2026
    You’ve got a champion. Someone inside the account who gets it. They love your solution, they’re fighting for your proposal, and they’re feeding you intelligence about the decision-making process. So you’re golden, right? Wrong. One reorganization, one promotion, one departure, and your deal could vanish overnight. Research from LinkedIn Sales Solutions analyzed thousands of enterprise deals and found something most salespeople refuse to believe: sales teams that build relationships with multiple stakeholders inside an account are 34% more likely to win. That’s the difference between hitting quota and missing it. Between a banner year and a brutal one. Why Single-Threaded Deals Die On average, 4-7 people influence a complex B2B buying decision. Even if you nail the pitch, you’re still just one voice in a conversation happening behind closed doors. A conversation where people you’ve never met are raising objections you’ll never hear. Where priorities you don’t know about are shifting the criteria. Your champion can be dismissed as “the person who likes that vendor.” But when you’ve got three advocates from different departments? Consensus wins deals. Your Champion Won’t Stick Around One in five of the people you’re counting on right now won’t be in their role twelve months from now. They’ll get promoted, reassigned, poached by a competitor, or laid off in the next restructuring. When that happens to your sole contact, your deal doesn’t just stall. It dies. The new person in that role has zero relationship with you, zero context on your solution, and zero incentive to champion something their predecessor started. But if you’ve built what top performers call “account insulation”—relationships with two, three, or four people across different departments and levels—the web flexes when someone leaves. It doesn’t break. Weak Ties Matter More Than You Think We’re trained to go deep with our primary contact. Build trust. Understand their pain points. Tailor every message to their specific needs. That’s not wrong. It’s just incomplete. In complex selling scenarios, influence often spreads through what researchers call weak ties—the casual, adjacent connections that link clusters of strong relationships. These are your amplifiers. A brief introduction. A shared article. A helpful insight that makes someone in operations remember your name when your solution comes up in a meeting you’re not in. These loose connections become the difference between a deal that stalls and one that scales. Think about how deals from referrals close. They close twice as fast as deals that start cold. Accounts with multiple contacts grow larger, stay longer, and refer more business. The pattern is clear. Get enough internal referrals, and you stop being the vendor someone works with. You become the partner everyone trusts. Five Mistakes That Keep You Single-Threaded Account multithreading fails most often before it ever really begins. Not because it is hard, but because salespeople sabotage it with impatience, poor judgment, or misplaced effort. If you recognize any of these behaviors, they are costing you leverage inside the account. Trying to build fifty superficial relationships instead of multiple deep, meaningful connections. Spray and pray doesn’t work in prospecting, and it doesn’t work in account multithreading.Asking for referrals before you’ve built credibility. You can’t extract value before you’ve created it.Failing to nurture the relationships you’ve already initiated. You can’t plant seeds and never water them.Ignoring the law of reciprocity. If you don’t offer value first—business insights, useful data, relevant introductions—people won’t feel any obligation to help you. You’ll burn through goodwill and get nothing back.Wearing out your welcome. If you’ve reached out multiple times with relevant insights and gotten silence, that’s a signal. Move on. How to Build Your Account Web With Multi-Threading Start by mapping the web of people connected to your account. Decision makers, influencers, skeptics, the quiet analysts whose opinions shape what the decision makers think. Write it down. Visualize the relationships you have, the ones you need, and the blank spaces in between. Then ask questions that open doors and show you recognize the decision is bigger than one person. “Who else on your team would have a point of view on this?” “Would it be helpful if I shared what other departments are doing with similar tools?” “Is there someone else who should see this?” Or use my favorite: “I need your advice on this.” That phrase invokes reciprocity and dramatically increases the probability they’ll give you the referral. When trust is formed, asking for a direct referral becomes an act of generosity rather than an intrusion. Frame it around value, not obligation. “Would you be willing to introduce me to your colleague in ...
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  • Why Your Sales Team is Underperforming — Patrick Lencioni on Working Genius

    Why Your Sales Team is Underperforming — Patrick Lencioni on Working Genius
    Feb 5 2026
    “You know, at the core of Working Genius, what it does is it allows us to avoid guilt and judgment—guilt about ourselves and judgment of others.” That’s Patrick Lencioni, bestselling author and organizational health expert, talking about his breakthrough Working Genius productivity framework on the Sales Gravy podcast. If you’re leading a sales team, this explains why high performers thrive in some roles and burn out in others. Right now, you probably have high performers who are miserable, rockstars who’ve lost their spark, and top reps who suddenly can’t hit quota. And you’re wondering—did you hire wrong, did someone lose their edge, or do you need to have “the conversation”? What if the problem isn’t the person at all? The Real Reason Your Best People Are Struggling Not all work is created equal, and your sales reps aren’t wired to do all of it. Lencioni stumbled on this insight while reflecting on himself. He’d show up to work loving his job and the people he worked with, yet swing from energized to frustrated without understanding why. His colleague asked, “Why are you like that?” Over a few hours, Lencioni and his team pinpointed six distinct types of work. Depending on which type you’re doing, you’re either energized or drained. Five years later, over 1.5 million people have taken the Working Genius assessment. Why? Most organizations force talented people into work that drains them, then blame them when they struggle. Most sales leaders hire a closer for their ability to seal deals, then wonder why they can’t prospect. They promote a quota-crusher into management, then watch them implode under administrative responsibilities. Or move an account manager into new business development and act shocked when performance tanks. The talent was there all along, but their positioning was wrong. Six Types of Work—and Why Most People Only Excel at Two Patrick Lencioni identified six distinct types of work that exist in every organization: Wonder (W): Spotting opportunities, asking big-picture questionsInvention (I): Creating new solutions, processes, or systemsDiscernment (D): Evaluating ideas, figuring out what will workGalvanizing (G): Rallying the team, getting people movingEnablement (E): Supporting others, clearing obstacles, making things happenTenacity (T): Following through, finishing tasks, closing deals Here’s what matters: most people are strong in two, competent in two, and are drained by the remaining two. And there are no good or bad geniuses. Your closer with natural Tenacity isn’t more valuable than your strategic thinker with Wonder and Discernment. Your rep who rallies the team (Galvanizing) isn’t better than the one who quietly enables everyone behind the scenes. Different geniuses are valuable in different ways. The goal is to build a team where all six are represented, and people work in their areas of strength. Force someone into work that drains them, and sales team performance tanks. Leave them in their genius zones, and energy and results skyrocket. Stop Judging Your People (And Yourself) You’ve probably got a rep right now who frustrates you. Maybe they’re brilliant in client meetings but terrible at following up. Maybe they generate incredible account strategies, but can’t stand the daily grind of outbound prospecting. Maybe they close deals but never update the CRM. Your first instinct is to judge them. “They’re not coachable.” “They don’t care about the details.” “They’re lazy.” Working Genius removes that judgment. It shows you that their struggle isn’t about character—it’s about wiring. A rep isn’t bad at follow-up because they don’t care. They’re bad at it because Tenacity isn’t their genius. A rep isn’t a bad team player because they don’t remove obstacles for others. Enablement isn’t their strength. And here’s the part most sales leaders miss: you need to stop judging yourself, too. You feel guilty that you hate certain parts of your job. You think you should be better at forecasting, or administrative work, or whatever drains you. But guilt about your own limitations makes you harder on your team. When you accept that you’re not built to excel at everything, you can extend that same grace to others. You stop punishing people for being human and start positioning them for success. Start With Self-Reflection Which activities give you energy? Which leave you drained? I’ll be honest about my own wake-up call. I travel over 300 nights a year, giving keynotes and working with clients. Last summer, I got to the point where I thought I was going to have a mental breakdown. Days stacked with short calls, client check-ins, alignment meetings, and podcasts. I was furious when I got to the office, and furious when I left because those days completely destroy my brain. I’m a wonderer and a thinker. I need space to ideate. Without that time, I can’t function. So I implemented a new ...
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  • Why Cold Calling Will Never Die (Ask Jeb)

    Why Cold Calling Will Never Die (Ask Jeb)
    Feb 3 2026
    Here’s a question that hits every sales professional right in the gut: What do you do when your email prospecting tanks and you’re staring at response rates that are circling the drain? That’s the question Tara asked on a recent episode of Ask Jeb on The Sales Gravy Podcast, and it’s one I hear constantly from SDRs, account executives, and even sales managers who’ve convinced themselves that cold calling is outdated. If you’re nodding along, thinking email is the future and cold calling is dead, you need to wake up. Email efficiency is going down without bounds, and if you’re not picking up the phone, you’re leaving money on the table. The Hard Truth About Email Prospecting Let me be blunt: Your email isn’t failing because the channel is broken. It’s failing because what you’re doing is terrible. Before you blame the medium, look in the mirror. Did people ignore your email because you sent them something genuinely personalized and valuable? Or did they ignore you because you followed up thirteen times in five days? Did they ghost you because your seven colleagues already called them that same day? The brutal reality is that most salespeople treat email like a spray-and-pray numbers game. They blast generic messages, add zero personalization, and then wonder why nobody responds. Meanwhile, they avoid the one thing that actually works: picking up the phone and having real conversations. Why Cold Calling Will Always Matter Cold calling isn’t going anywhere. It never has been, and it never will be. You want to know why? Because sales is a human business. People buy from people they trust, and you can’t build trust through automated emails that sound like they were written by AI. A phone call gives you something email never can: the ability to prove you’re a real human being who’s genuinely there to help, not just to pitch and sell. When you call someone and say, “Hey, I sent you an email last week with this case study because I saw you talked about this at the Outbound Conference,” you’re showing them you did your homework. You’re not just another robot in their inbox. Here’s a line I love: “Would I be the worst salesperson in the world if I didn’t also try to call you?” It’s honest, it’s human, and it cuts through the noise. You Don’t Know What to Say? Make the Calls The number one excuse I hear from salespeople: “I don’t know what to say.” Here’s my advice: Make one hundred calls and talk to people. They’ll teach you. You’re going to learn what not to say. You’re going to start seeing patterns in how your prospects think, what problems they face, and what language matters to them. This is how you develop business acumen that separates you from the pack. You can’t learn it behind a keyboard. I was in an alignment call today with a new client, and they said, “You totally understand us.” Why? Last week, I was with a business adjacent to their industry, learned their language, and pulled that knowledge into the next call. Use Tools to Compress Your Learning Curve Use tools like ZoomInfo to accelerate your learning curve. At Sales Gravy, we use it every day to find information about people, see what they’re doing on our website, and get intent signals that build our lists automatically. You can use these tools to learn the language of industries you’re breaking into. You can see company news, understand their challenges, and show up on calls sounding like you belong. But here’s the key: The tool doesn’t make the call for you. It gives you the ammunition. You still have to do the work. Be Strategic and Resourceful Here’s a strategy most salespeople are too lazy to try: If you’re having trouble getting through to a decision maker, call someone else in the company who’ll actually talk to you. Selling HR services? Call a sales rep. They’ll talk your ear off about the company and might even make an introduction. Try this: “Hey, I know you’re in sales. I’ve been trying to get hold of Joseph for nine months. Is there any way you could help me out?” That’s not being cheesy. That’s being resourceful. But you have to be genuine. You can’t just ask for something without building rapport. Your Action Plan If you’re struggling with email effectiveness: Pick up the damn phone. Stop making excuses about why cold calling doesn’t work. It works if you work it. Get comfortable being uncomfortable. Introducing yourself to strangers will never be easy, but it’s the price of admission for being great at sales. Use data strategically. Build sequences that interweave multiple channels over 30, 60, 90 days. Email, phone, LinkedIn, video. Give yourself the best odds. Don’t oversell on the cold call. A little interest isn’t an invitation to vomit your pitch. Your job is to earn the next conversation. Make one more call. At the end of the day, when you’re tired, make one more call. That’s where discipline separates ...
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  • First Month Sales Results Gut Check (Money Monday)

    First Month Sales Results Gut Check (Money Monday)
    Feb 2 2026
    On this first Monday of the second month of the year, it’s time for a gut check. First, we need to check where we are against our new year goals. Next, we need to take stock of our first month’s sales performance and make adjustments. We’re just a little more than 30 days away from our New Year’s intentions, resolutions, and goals. A month ago, we set out into the new year with hope and ambition that this year would be our best ever and that we’d make positive lasting changes in our lives. It’s Easy to Slip Off the Track You’ll remember that discipline is sacrificing what you want now for what you want most. But as time goes by and sticking with new habits gets more challenging, it’s easy to forget what motivated us to make the changes in the first place. It’s easy to let down our guard and go back to our comfort zone. The farther away we get from our intentions, the more likely it is that we allow our discipline to slip and get off track. It’s just human nature. Small Slips in Discipline Can Add Up Quickly Let’s say you kicked off the new year determined to have your best sales year ever, and you knew that meant filling your pipeline daily by getting Fanatical about Prospecting. But upon reflection, you realize that days have passed since you picked up the phone, knocked on a door, or talked with customers. You’ve been making excuses to avoid the very activities that move you closer to your goals. I’ll admit that it happened to me just this past week. This month has been non-stop travel — 12 flights, 10 cities, 8 keynotes, 5 full days delivering training to sales teams. Toward the end of the week, I got tired, made excuses, and let my exercise and nutrition routine slide. This was something I promised myself I wouldn’t do when the year started. I know that if I don’t stop right now and recommit to my goals, then there is a good chance that I’ll continue down this negative path — because it’s easy. Revisit Your Goals and Resolutions This is exactly why NOW is a good time for a gut check and a look in the mirror. Pause and carve out time today to revisit your goals, resolutions, and intentions. Sit down and think about what you decided to achieve back in early January. Visualize what it was that motivated you. Picture what you want most and where you want to be at the end of this year. Go back and re-listen to the Money Monday episodes on building a personal business plan, reflection vs. regret, and why personal goals are essential for sales discipline. Then recommit to your goals. Remember the feelings you had when you set them, and make an intentional decision to get back on track. Evaluate Your First Month’s Performance Against Your Sales Goals Next, step back and evaluate your first month’s sales performance. As you do, you’ll likely find one of three scenarios: You Crushed It – You had a killer month and blew your goals out of the water.You Were Average – You hit quota or did “okay,” but you know you’re capable of much higher performance.You Bombed – You missed your number and ended the month worse than you hoped. Great Sales Month If You Crushed it, and you’re at the top of the ranking report, fantastic, congratulations! But be very careful not to let off the gas. It’s likely you worked very hard last month to achieve these results. There will be the temptation to take a breather. Trust me, if you do, this complacency will come back to bite you. Now is the time to recommit to doing the activity that fueled your success last month so you don’t end up with a lackluster February and a disastrous March. In other words, you’ve set the foundation for a huge year, take advantage of what you have accomplished, and keep the pedal to the metal! Average Sales Month If you had an average or just OK month — maybe you hit quota, maybe you came close, but you know you’ve got more in the tank — then it’s time for some honest self-reflection. Ask yourself: What held you back from greatness?What could you have done differently that would have resulted in higher sales productivity? Maybe you needed to prospect harder. Perhaps you could have pushed a little harder to close some of your pipeline opportunities. It could have been that your pipeline wasn’t big enough from the start, and you ended up scrambling to make your numbers, but otherwise, you did everything right. It’s okay, you haven’t hurt yourself. You are still in a good position to have a great year. But you’ll need to identify your performance gaps and plan to overcome them in February. This is a good time to sit down with your coach or mentor, break down your performance, and get guidance on where you can make tweaks and get better. If you don’t have a coach and you want to talk with someone, go to https://salesgravy.com/coach to get help. Bad Sales Month If you bombed, if your month was downright awful, then you’re going to need to move fast to make adjustments....
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  • Why Founder-Led Sales Teams Struggle to Scale

    Why Founder-Led Sales Teams Struggle to Scale
    Jan 29 2026
    “Buyers want a machine, a sales machine, not a mystery. If the sales machine only works because of the founder, it’s not that valuable. It’s actually quite risky.” Chris Spratling, founder of Chalkhill Blue Limited and author of The Exit Roadmap, shared this on a recent episode of the Sales Gravy podcast. He works with business owners preparing to sell their companies, helping them get operations, finances, and sales engines ready for new ownership. That insight cuts straight to the reason so many founder-led businesses hit a ceiling they can’t break through. If you are a founder who still carries most of the revenue, or you have a founder-led sales team that depends on you to close critical deals, this is bigger than exit planning. It determines whether your business can grow beyond your personal capacity. The Golden Handcuffs Problem You built the business. You know the product better than anyone. You can sell it without thinking. That is exactly where the risk starts. When major clients only trust you, when your sales process lives in your head, when new reps struggle to replicate what comes naturally to you, you aren’t running a sales operation. You are running a one-person engine with a support team around it. Spratling calls this the “golden handcuffs.” It looks like success from the outside, but underneath, it creates dependency. Every time you step in to save a deal, you reinforce the idea that the business only works when you are involved. Most founders focus on how this affects valuation at exit. Fewer recognize the more immediate cost. That dependency limits how fast the company can grow right now. https://www.youtube.com/watch?v=VEBLyaOy9XQ Where Founder-Led Sales Breaks Down The transition from founder-led sales to a functioning team is where momentum often stalls. You hire your first salesperson. They do well. Then a second. Then a third. Suddenly, deals slow down, messaging gets inconsistent, and you find yourself pulled back into conversations you thought you had delegated. They don’t sell the way you do. They miss cues you catch instinctively. They hesitate where you would push forward. So you jump in, coach through objections, and close deals yourself. What feels like instinct is actually a method you developed through hundreds of conversations. The problem isn’t that your team lacks talent, but that your approach has never been translated into something they can use without you standing next to them. As long as that stays true, scale will remain out of reach. Turning Intuition Into a Usable Process The hardest shift for founder-led teams is codifying what the founder does without thinking. You know which deals are worth pursuing. You know when to apply pressure and when to step back. You know how to redirect a conversation when resistance shows up. That knowledge is pattern recognition built over time, and it can be used to create a process. Start by defining how deals actually move through your pipeline. Not a generic framework pulled from a template, but the real stages your customers pass through, with clear criteria for each transition. What has to be true before a lead is qualified? What information must be present before a proposal goes out? Then look at discovery. What questions do you ask every time? What do you listen for before positioning your solution? Which objections show up consistently, and how do you respond when they do? The goal is to document the structure beneath the conversations so that someone else can navigate the same terrain with confidence. Why Your CRM Is Not Pulling Its Weight Most founder-led teams have a CRM, but they only use it to track contacts and deal size. However, a functioning, high-performing sales system treats the CRM as a learning tool. That means capturing more than surface-level data. It means recording what buyers actually say, why deals move forward, where they stall, and who influences the decision. When that information is tracked consistently, patterns become visible. You see which prospects convert fastest, which objections actually kill deals, and where momentum typically breaks down. That insight does more than improve forecasting. It gives you a concrete way to train new reps based on real deals you have closed, not abstract theory. Three Steps to Build a Sales Engine That Does Not Depend on You The objective isn’t to remove yourself from sales completely. It’s to make your involvement a choice rather than a requirement. Step 1: Define Clear Qualification Criteria Your team needs to know which leads are worth pursuing and which ones are a waste of time. If you’re constantly redirecting their focus, you haven’t defined “good fit” clearly enough. Get specific—industry, company size, buying triggers, decision-making structure. Step 2: Create Documented Playbooks How do you handle discovery? What’s your approach to proposals? How do you navigate the closing process? Your team needs a ...
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  • Jeb Blount’s 3 Non-Negotiables for Modern Sales Success (Ask Jeb)

    Jeb Blount’s 3 Non-Negotiables for Modern Sales Success (Ask Jeb)
    Jan 27 2026
    Here’s a question that’ll change how you think about this profession forever: What’s the one moment that reveals you’re built for sales success? For most people, that moment never comes. They stumble into sales, struggle with the stereotypes, and either quit or spend their entire career fighting against what they think selling is supposed to be. But for those of us who get it, there’s a moment of clarity so powerful it changes everything. Mine happened in high school when I was chasing a girl and ended up on the yearbook staff. Thirty days later, I handed over $3,800 in checks while everyone else struggled to hit their $300 quota. The Sales Crack Moment When Mr. Hall at Hall’s Hardware Store wrote me that first check for a yearbook ad after I had done little more than ask outright for the money, something clicked. This wasn’t complicated. Walk in, shake hands, present value, and people give you money. While my classmates were paralyzed by the same stereotypes you hear today (“I’m not a salesperson”), I was out there having conversations. That’s all prospecting really is. Talking to people. The gasp in that room when I revealed my numbers? That was better than the money. That was the competitive fire igniting. That was me realizing I could outwork, outsell, and out-earn anyone if I just committed to the process. https://www.youtube.com/watch?v=J7dOBVvYHCs The Discipline Problem Most Sellers Miss Here’s what nobody tells you about sales success: It’s not about talent. It’s not about charisma. It’s about the ruthless execution of proven processes. By the time I was 21 or 22, I was making $300,000 in the early nineties. That’s equivalent to making close to a million today. Not because I was special, but because I understood something fundamental that most people never figure out: The more people you talk with, the more you sell. And here’s the beautiful part. There are lots of people to go talk with. The pipeline never runs dry if you’re willing to fill it. The Three Non-Negotiables for Modern Sellers The future of selling is blending. Not choosing between video and phone and in-person. Blending all of them based on one critical question: What communication channel gives me the highest probability of capturing my desired outcome at the lowest cost of time, energy, and money? When I started selling, we had two channels. Maybe three if you count snail mail. Phone and in-person. That’s it. Today? You’ve got a dozen ways to connect. WhatsApp lets you text, call, and video chat almost instantly. The options are endless. But here’s where Gen Z sellers (and honestly, every generation) screw this up: They get single-siloed. “I’m only good at email.”“I only do video calls.”“I hate the phone.” That mindset is killing your income potential. You need to be good at everything. Master every channel. Because the channel doesn’t matter. The outcome does. Synchronous Beats Asynchronous Every Single Time Here’s the second non-negotiable to sales success: Stop hiding behind asynchronous communication. We do deals in a synchronous world. Real-time conversations. Phone calls. Video meetings. Face-to-face interactions. If you think you can close business through email threads and text messages, you’re delusional. Why? Because robots can write better emails than you can. AI can craft more persuasive text messages. But sales is the ultimate human career in the age of AI precisely because of the human connection required in synchronous conversations. Lead with phone calls. Get face-to-face when the deal size justifies it. Use video when it makes sense. But always, always prioritize real-time conversations over digital hide-and-seek. Ask Questions and Actually Listen The third non-negotiable is mastering the art of asking great questions and listening to the answers. People make five decisions before they buy from you: Do I like you? Do you listen to me? Do you make me feel important? Do you get me and my problems? Do I trust and believe you? Notice what’s not on that list? Your product features. Your company’s awards. Your clever sales pitch. They’re evaluating you. Your ability to connect. Your capacity to understand. Your commitment to making them feel important. And the only way to get five affirmative answers to those questions is through synchronous conversations where you ask intelligent questions and actually listen to what they’re telling you. The Make It Rain Principle When Mr. Rouse made me editor of the yearbook after I brought in $3,800, I learned something that shaped my entire career: When you can make it rain, you can get anything you want. That principle holds true whether you’re selling yearbook ads in high school or enterprise software to Fortune 500 companies. Revenue solves problems. Performance opens doors. Results create opportunities. Most people in sales stumble into it. They took the job because it was available. They stick with it ...
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