• Sales Prospecting Sequences and ZoomInfo: Buy or Die Without Burning Bridges (Ask Jeb)
    2025/09/16
    Here's a question that'll keep you up at night: What do you do when you believe in "buy or die" but you're terrified of ruining future opportunities with annoying prospecting sequences? That's exactly what Angie Anderson asked during a recent Ask Jeb session, and it's a problem that's plaguing salespeople everywhere. Angie subscribes to the buy or die mentality but doesn't want to destroy her odds of winning in the future by becoming the prospect's worst nightmare. If you're nodding your head right now, you're not alone. The tension between persistent prospecting and respectful relationship building is one of the biggest challenges facing modern sales professionals, and getting it wrong costs you deals—both now and in the future. The Buy or Die Misconception That's Killing Your Pipeline Here's the brutal truth: Most salespeople completely misunderstand what "buy or die" actually means. They think it's about hammering prospects until they crack, but that's not persistence—that's harassment. Real buy or die mentality recognizes that the prospect is never not a prospect, but sometimes now is not the right time. The key is knowing when to push and when to pull back. Your sequence length and touch frequency should be driven by one critical factor: deal complexity and account size. Short Cycle Sales Need Short, Aggressive Sequences Run 10-14 touch sequences over 10-30 days with touchpoints every 2-3 days. These prospects have buying windows that are typically always open, and the stakes are relatively low. Complex Accounts Require Long-Term Relationship Building For massive, high-value accounts, you could run sequences that extend up to two years. Touch them monthly or quarterly to stay top of mind, waiting for the right opportunity window to open. The magic happens when you track meaningful engagement. In any properly executed sequence, 30-50% of prospects will give you some form of signal—yes, no, or even "go away." All of these responses give you something to work with. But here's the critical part: When you get complete radio silence from the other 50%, you stop. Pull them out of your sequence, slot in fresh prospects, and circle back in 90 days or six months. You have infinite time to go after them—use it strategically. Why Generic Messages Get You Blocked Every Time This brings us to the second major challenge facing modern salespeople: crafting relevant messages that actually resonate with busy prospects. James Baldwin perfectly captured this struggle when he asked about leveraging tools like ZoomInfo to create relevant messaging. He sees tons of information but doesn't know what to use or how to use it effectively. This is where most reps completely miss the mark, and it's costing them relationships. The Research Failure That Destroys Credibility Want to know the fastest way to get permanently blocked? Send a message that screams "I know nothing about you or your business." This happened to me recently with a rep from a major software company. They did everything technically right—multi-channel approach, proper timing, professional voicemails—but they failed at the most critical element: relevance. They prospected Sales Gravy without doing even basic research. My LinkedIn profile was right there. My content was everywhere. I've literally said thousands of times that if you mention my books when prospecting me, I'll almost always respond. But they were too lazy to look. That's not persistence—that's sales malpractice. How to Turn Data Overload Into Relevant Conversations The problem isn't lack of information—it's information overwhelm. Modern tools give you access to massive amounts of data, but most reps freeze up trying to figure out what matters. The solution is asking better questions of your data. Instead of just building lists, use AI-powered tools to ask specific questions: "What are three conversation starters that would make this CEO interested in talking with us?
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    14 分
  • How Charlie Kirk Disagreed Is More Important Than What He Believed
    2025/09/15
    I had intended for this Money Monday to be something powerful, a new message that would get you fired up for this week and this season. But last week, while delivering training to an amazing group of young salespeople with wide-open minds, I learned that Charlie Kirk had been assassinated. It disturbed me deeply and I feel compelled to deliver this message. The Assassination That Shook America On September 10, 2025, Charlie Kirk was fatally shot while addressing an audience at Utah Valley University in Orem, Utah. A young man, thirty-one years old with his whole life ahead of him, was killed for no other reason than someone disagreed with him. After learning about the assassination, I found myself incredibly disturbed that a person in the public square could just be shot and killed like that – murdered right in front of everyone. So I did what I always do when I want to understand something: I started learning. I watched hours and hours, dozens and dozens of Charlie Kirk's videos to learn more about the man, his message, and why someone would think it would be okay to assassinate him. I still haven't found the answer to that last question. This Isn't About Politics Before I go any further, let me be crystal clear: This is not a political message. This is not a religious message. It is about how we treat each other as human beings. If you know me, if you've been to my events or training, you know I never talk about politics or religion. If you look at my social media feeds on any channel, you won't find much that would help you understand what my politics or religion are. Do I have convictions? Yes. Do I believe certain things? Yes. But they're my beliefs, and I keep them to myself because my job is to train salespeople. I'm a sales author, trainer, expert, and consultant. That's my lane. I train salespeople no matter what they believe. I train salespeople no matter what their religion. I train salespeople and help salespeople no matter where they're from or what their walk of life is. I don't care where you come from because my entire purpose, my reason for being on earth, is to help you sell more, help you gain confidence, and be there to help you with your biggest sales questions and challenges. What Charlie Kirk's Example Taught Me What I discovered in watching those videos was something that transcends political beliefs. Charlie Kirk's example was his willingness to go sit down face-to-face with people who disagreed with him, sometimes vehemently, and just have a conversation. And do it respectfully. I noticed something remarkable in his videos: more than once, he said, "You know what, I stand corrected." Someone would come to him with a different set of facts, and he would say, "Okay, that sounds right. I agree with you." In many cases, he would shake the person's hand after a debate. He was respectful. It was never about the person. It wasn't personal. He didn't hate the person. He had conversations about their ideas. How Charlie Kirk disagreed mattered. That is what we need to get back to. Not someplace in the future – today, right now. The Human Cost I watched his wife Erica's message to the world, and I found myself on an airplane as a grown man with tears streaming down my face, trying not to let everyone see that I was crying. It was heartbreaking watching her pain. She has two kids – one is one year old, one is three. That assassin changed their lives forever. I can't imagine when one of them gets older and either finds the video of their daddy getting assassinated or someone puts it in front of them. If you step into that frame for just a moment with your human empathy, it will make you hurt. Charlie's children will be raised with stories instead of memories, photographs instead of laughter, and silence where their father's voice should have guided and loved them. The Conflict We All Face Everywhere in our lives with other people, we have disagreement.
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    12 分
  • The One-Question Revolution That Transforms Sales Discovery
    2025/09/11
    What if one simple discovery question could close your next big deal? Here’s the one I used: “Tell me what’s going on with your team?” Then I shut up and listened. The buying committee talked, debated, and worked their way toward their own clarity. By the end of the call, they had essentially closed the deal for me. I barely said a word. That’s not a fairy tale—it happened. And it proves why most sales discovery fails: reps focus on their checklist and pitch instead of helping the buyer gain clarity. The Certainty Crisis Killing Your Deals Dr. Lorenzo Bizzi joined The Sales Gravy Podcast and revealed a simple truth: Buyer uncertainty kills deals. Traditional sales discovery often increases that uncertainty. Rigid qualifying questions, seller-centric agendas, and shallow data gathering make buyers feel misunderstood and cautious. When you approach discovery this way, you’re eroding trust. Sure, buyers are evaluating your product—but they’re also evaluating whether you understand their world. And if you can’t help them gain clarity, even the best solution won’t move the deal forward. The Science of Deep Sales Discovery The most effective influence tactic isn't charm, rapport, or even product demos. It's clearly displaying the arguments and reasons why your solution works for their specific situation. But you can't build rational arguments until you truly understand the problem. And you can't understand the problem until you master deep discovery. Deep discovery operates on two levels: The Organizational Level: What metrics matter to the company? What are the measurable business outcomes they're trying to achieve? What's the cost of inaction? The Individual Level: What's at stake for each stakeholder personally? How will this decision impact their performance review, their standing with leadership, and their career trajectory? Remember: Organizations don't make decisions. People do. The Power of One Question The most powerful discovery conversations start with one well-crafted, open-ended question that invites the buyer to tell their story—not your story about how great your product is. The question I used—"Tell me what's going on with your team?"—worked because it was: Open-ended, with no leading assumptions. Centered on their world, not my product. Neutral, without judgment or bias. Broad enough to go anywhere. When you ask the right question and then listen, the buyer starts convincing themselves. They begin connecting the dots between their current situation and what they need to change. And here's the key: If the buyer says it, it's the truth. If you say it, you're just another salesperson spinning a pitch. Cognitive Empathy Is The Difference Maker Dr. Lorenzo Bizzi defines several types of empathy. But for salespeople, the distinction that matters is simple: affective empathy pulls you off course, while cognitive empathy keeps you sharp, connected, and in control. Affective empathy—actually feeling what your buyers feel—will drain your energy and cloud your judgment. When they're frustrated, you get frustrated. When they're uncertain, you become uncertain. Cognitive empathy is different. It’s the ability to recognize and understand what your buyer is feeling without taking it on yourself. You stay clear-headed and outcome-focused, while still connecting deeply with their situation. In discovery, cognitive empathy shows up in the emotional nuance most salespeople miss—a pause before they answer, a change in tone, or hesitation in their voice. That’s your cue to lean in, ask a clarifying question, and uncover what’s really driving their hesitation. "You paused when I asked about your current system. What's on your mind?" "I heard some frustration in your voice when you mentioned the timeline. Help me understand what's driving that." Deals get won in the emotional subtleties that surface-level discovery never uncovers.
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    37 分
  • How Emotional Regulation Impacts Sales Performance (Ask Jeb)
    2025/09/09
    Here's a question that'll make you rethink everything about sales performance: What happens when your team has all the skills, tools, and training they need, but they're still underperforming because they can't regulate their emotions under pressure? That's exactly what Natalie Brooks from Charlotte discovered when she noticed how drastically emotions were impacting her team's performance during tough selling days. Meanwhile, salespeople like Jordan from San Diego are making decisions they later regret—pushing forward on deals they know are wrong just because they look good on paper. If you're nodding your head right now, you're witnessing one of the most overlooked aspects of sales performance: emotional regulation. And it's costing you deals, talent, and revenue. The Dysregulation Problem: When Emotions Hijack Performance Here's the brutal truth: When you're emotionally dysregulated or your nervous system is hijacked by stress, focusing on anything becomes nearly impossible. Your best discovery questions go out the window. Your qualifying discipline disappears. Your prospecting consistency evaporates. Think about it. You can have the perfect sales process, but if your rep is in fight-or-flight mode from a string of rejections, they're not executing that process effectively. They're just going through the motions while their emotional state sabotages their performance. This isn't just about "feeling better." This is about creating the mental and emotional foundation that allows elite sales performance to happen consistently. Why Most Sales Leaders Miss This Completely The reason most sales organizations ignore emotional regulation is the same reason they obsess over talk time metrics—it's easier to focus on activities than outcomes. It's much simpler to say "make more calls" than to create an environment where your team feels safe enough to regulate their emotions and perform at their peak. But here's what happens when you ignore the emotional component of sales: Your reps start making fear-based decisions. They chase deals they know are wrong fits because they're afraid of having an empty pipeline. They avoid difficult conversations because rejection feels personal. They burn out because they're running on adrenaline instead of sustainable energy. Meanwhile, your top performers aren't just skilled, they've learned to manage their emotional state in a way that supports peak performance. The Three Pillars of Emotional Regulation in Sales Personal Regulation: The Foundation Everything starts with personal habits that support emotional stability. Your "why" becomes your anchor during tough moments. When you're tired, exhausted, or questioning what you're doing, that purpose pulls you through. But purpose alone isn't enough. Your daily habits outside of work create the foundation for emotional regulation at work. Sleep, nutrition, exercise, stress management—these aren't "nice to haves." They're the infrastructure that supports your ability to stay sharp and focused when deals get challenging. Team Regulation: Creating Safety As a leader, you have a responsibility to create psychological safety where your team can regulate together. This might look like mid-day resets where everyone takes a few deep breaths or does a quick activity to release tension from difficult calls. The key is consistency. When emotional regulation becomes part of your team culture—not just something you talk about during tough times—it shows that peak performance includes emotional wellness. Process Regulation: Trusting Your System Here's where emotional regulation meets sales discipline. When you have clear qualifying standards and you trust your process, you don't have to make emotional decisions about which deals to pursue. Ultra-high performing salespeople have probability discipline because they recognize they only have so many hours in the day. They create rules they can live by rather than relying on gut feelings in the mo...
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    20 分
  • The 4-Step Lead-Generating Podcast Strategy Sales Pros Swear By
    2025/09/04
    While your competitors are stuck in voicemail purgatory, a small group of top performers has unlocked a secret pipeline of qualified sales leads. They've discovered how to stop chasing and start attracting, all by generating warm leads through podcast interviews. Not by starting their own shows, but by treating every podcast appearance as a lead generation machine built on conversation and credibility. As Molly Ruland, CEO of Heartcast Media, puts it, "You don't need a hundred new clients tomorrow. Two people who really like you and understand your business talking about you in rooms you're not in can change your pipeline." This mindset shift transforms how you approach every conversation so that it compounds into trust, referrals, and revenue. The Real Problem with Your Pipeline You’re sending out hundreds of emails, making dozens of cold calls, and hoping something sticks. It’s exhausting—and it rarely produces the kind of relationships that lead to real opportunities. Your prospects don't want to be sold to. They're sick of transactional relationships. They want genuine conversations and solutions from people they trust. This is where most salespeople fail to find a qualified sales lead. They're focused on the sale, not the connection. So what’s the alternative? It’s learning to treat every podcast appearance as more than just an interview. Done right, podcasts become a warm stage where you can demonstrate expertise, build credibility, and start relationships that turn into pipeline. To make this work, you need a simple, repeatable system—a four-step process that transforms a single podcast conversation into a flow of qualified leads. Step 1: Finding the Right Stage The process is about being smart, not getting famous. You don’t need to get on the biggest podcast in the world. You need to get on the right podcast. The right podcast is where your ideal customer profile (ICP) is already gathered, listening, and learning. A show with 50 listeners who are all in your target market is a thousand times more valuable than a show with 50,000 listeners who will never buy from you. How do you find the right podcasts? Ask your best clients what they listen to. Research key influencers in your space. Look for shows that specifically address the problems you solve. Your goal is simple: Find and get on shows hosted by industry connectors, aggregators, and experts who have already earned the trust of your prospects. This allows you to skip the cold outreach and get a warm introduction to your next qualified sales lead. Step 2: The Introduction That Doesn’t Sound Like a Pitch Once you’ve identified your target shows, the next step is getting invited. This is a crucial moment. A generic email won’t cut it. You have to craft a message that offers value, not asks for a favor. Your outreach needs to be personalized and direct. Don’t talk about how great you are. Talk about the host’s audience. Explain why your expertise, insights, or unique perspective will provide undeniable value to their listeners. Reference a specific episode or a past guest to prove you’ve done your homework. And don’t limit yourself to email. LinkedIn is one of the most effective platforms for securing podcast invitations. Sending a thoughtful, personalized LinkedIn message—paired with a strong profile that showcases your expertise—positions you as a credible guest. When a host sees you consistently sharing relevant insights on LinkedIn, your ask feels natural instead of opportunistic. When you offer to help them provide a great episode, you position yourself as a partner. You’re not begging for airtime. You’re offering a valuable conversation. This approach immediately sets you apart and begins the relationship-building process that is essential to finding a qualified sales lead. Step 3: Mastering the Conversation The interview itself is not a sales call. Your goal is to be a helpful,
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    32 分
  • How to Overcome Sales Burnout and Stop Crashing During Long Days (Ask Jeb)
    2025/09/02
    Day in the life of a rep heading toward sales burnout: You wake up ready to crush your sales goals, skip breakfast to get an early jump on calls, grab fast food between appointments, and by 2 PM you're mentally checked out, struggling to focus on that critical prospect meeting. That's the reality facing Angela Mendez from Austin and Marcus Taylor from Denver. Angela's crashing every afternoon when she skips meals or eats on the go. Marcus is burning out fast juggling a packed pipeline and back-to-back Zoom meetings. If you're nodding your head right now, this article is your wake-up call. Because the energy crisis and burnout epidemic in sales isn't just about being tired—it's costing you deals, destroying your performance, and stealing your edge when you need it most. Why Sales Reps Experience Afternoon Energy Crashes and How to Fix Them Let's start with the brutal truth about energy management: Your brain is an engine, and like any engine, it needs the right fuel to perform. When you skip meals or grab whatever's convenient, you're essentially putting sugar water in a Ferrari and wondering why it's sputtering. Here's what happens when you don't fuel properly: Your blood sugar crashes, your focus evaporates, and your personality literally changes. You become irritable, indecisive, and ineffective—exactly when you need to be sharp, confident, and persuasive. The solution isn't complicated, but it requires preparation and discipline. Start with breakfast—period. This isn't negotiable. You need something that gives you a slow burn: oatmeal with fruit, protein like eggs, something that keeps you steady until lunch. If you don't eat protein in the morning, you'll be hungry by 10 AM and making poor food choices. Pack your day the night before. Get a cooler. Fill it with real food: apples and almond butter, walnuts, dried fruits without added sugar, vegetables and hummus. Keep fresh fruit and vegetable juices without added sugar in small bottles. This isn't about being a health fanatic—it's about maintaining peak performance when deals are on the line. Here's the game-changer: Don't wait for fatigue or extreme hunger. Stay ahead of it. The moment you feel your energy dipping, that's too late. You should be fueling consistently throughout the day, not rescuing yourself from a crash. And here's a pro tip that might sound simple but works: carry apples everywhere. When you start getting hungry and your personality begins to shift, an apple gives you just enough sugar and energy without the crash that comes from processed snacks. It's your emergency reset button. How Back-to-Back Meetings Create Sales Burnout and What to Do Instead Now let's talk about Marcus's burnout problem, because this one hits close to home for every salesperson drowning in Zoom fatigue and calendar chaos. Here's the hard truth: Being on camera wears you out way faster than face-to-face meetings. If you're scheduling yourself back-to-back-to-back without recovery time, you're your own worst enemy. There's no formula that's going to solve the problem of walking from one meeting directly into the next meeting into the next meeting. Your brain can't handle it, and your performance will suffer. Take control of your calendar. I know this sounds obvious, but how much of your scheduling nightmare did you do to yourself? How often do you say yes when you should say no? How many meetings do you accept because of FOMO—fear of missing out—when the meeting is actually superfluous? Audit your last 30 days of meetings. Really look at them. How many could you have declined? How many were necessary for moving deals forward versus just making you feel busy and important? Here's what's really happening: You're filling your calendar to prove your value and demonstrate how busy you are. But a packed calendar isn't a badge of honor—it's a recipe for burnout and poor performance. It takes confidence and self-ownership to say,
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    9 分
  • 5 Sales Leadership Skills You Can’t Fake
    2025/08/29
    Leadership is the single most important factor in a sales team’s success. You can have talented reps, strong products, and a solid sales process, but without effective leadership, performance stalls. As Duff Tucker, Sales Trainer, puts it on this episode of the Sales Gravy Podcast: "You have to model the behaviors that you want your team to live out. When you model those, you get a lot of credibility. You have respect. You have influence.” In today's hyper-competitive sales environment, your team has choices. Top performers can work anywhere. Average reps will coast if you let them. But the teams that consistently crush quotas, retain top talent, and create cultures where everyone wants to win all have one thing in common: a leader who has mastered the fundamental skills that turn potential into performance. Here are five leadership skills every sales manager must master to drive their team to the next level. 1. Clear Communication: No Confusion, No Excuses Sales teams don’t fail because of a lack of talent—they fail because of unclear expectations. Leadership starts with communication. If your reps don’t know exactly what you expect, how you measure success, or where they’re falling short, you’re setting them up to miss the mark. Clarity means: Defining priorities: What activities matter most (calls, meetings, proposals) and why. Eliminating ambiguity: No mixed signals, no “read between the lines.” Giving feedback in real time: Don’t wait for quarterly reviews to correct course. Practical tip: After every meeting, send a short recap of agreed actions and timelines. It reinforces expectations and removes excuses. Vague leadership creates vague results. 2. Goal Setting & Vision: Building Direction, Not Just Numbers A sales leader isn’t just a scoreboard watcher. Your job is to give your team something bigger to aim at than just “hitting quota.” Without a clear vision, teams drift into reactive mode and lack initiative. People perform better when they’re chasing a clear, meaningful vision. Effective goal setting requires more than revenue targets. It’s about: Tying team goals to organizational strategy. Breaking big objectives into manageable activity benchmarks. Painting a picture of what winning looks like so reps can see themselves in it. Practical tip: Start every month by walking your team through why their goals matter and how success impacts the company, the customer, and their own careers. When reps buy into the vision, they push harder to achieve it. 3. Coaching: From Boss to Builder Micromanagers kill momentum. Coaches create it. Leadership in sales means shifting from telling people what to do to building people who can do it themselves. Great sales coaching involves: Observation: Ride-alongs, call reviews, pipeline inspections. Targeted feedback: Specific, actionable, focused on behaviors, not personality. Development mindset: Every interaction is a teaching moment. Practical tip: Block weekly one-on-one coaching sessions that focus on skills and pipeline health. Ask questions that uncover roadblocks instead of delivering lectures. Consistently coached reps outperform those left to figure it out alone. 4. Adaptability: Leading Through Change Markets shift, customers evolve, and strategies that worked yesterday won’t guarantee tomorrow’s success. The best leaders view challenges as opportunities. Adaptability looks like: Adjusting sales strategies with confidence. Staying ahead of industry trends, not reacting late. Modeling resilience when things don’t go according to plan. Practical tip: Hold monthly “market pulse” sessions where you and your team discuss shifts in buyer behavior, competitor activity, and emerging tools. This keeps your team agile and ready to move, rather than stuck waiting for direction. 5. Accountability & Recognition: The Performance Balance Leadership is about balance, not being a cheerleader or tyrant.
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    23 分
  • 5 Ways to Stop Sales Territory Disputes From Destroying Your Team (Ask Jeb)
    2025/08/26
    Here's a question about sales territory disputes that'll make your head spin: What do you do when overlapping territories and shared relationships turn your sales team into a collection of lone wolves fighting over who owns what? That's the exact predicament faced by Kayla Lujan, VP of Sales at Down to Earth Landscape and Irrigation, in Orlando, Florida. Her team manages defined territories, but their business model creates inevitable crossover with HOA managers who oversee multiple properties spanning across different reps' territories. As she put it: "I've really seen the team kind of lose focus on working as one or team selling and more of … a what's mine versus working together." If you're nodding your head right now, you're not alone. Territory disputes are one of the most destructive forces in sales organizations, and they're costing companies their collaborative culture and their best deals. The Psychology Behind Sales Territory Wars Salespeople are wired to win. And when territories overlap, that competitive drive turns inward, creating internal battles that hurt everyone. I learned this lesson the hard way when I was a VP of sales managing local and regional account executives. We had big regional accounts sitting in local territories, and the fighting was relentless. Local reps would work around the system, hide opportunities, and go through back doors to protect "their" accounts. The result? We lost major deals because the wrong person with insufficient skills was working them solo, or we'd win the business only to have explosive commission disputes after the fact. But here's what shocked me most: When we gave people the choice between money or credit on the ranking report, they fought harder over the credit than the commission. They'd forgo 100% money but wage war over who got recognition for closing the deal. That tells you everything you need to know about sales psychology. It's not just about money—it's about winning, recognition, and status. The Real Cost of Territorial Thinking Territory disputes create uncomfortable team meetings and destroy your sales effectiveness in three critical ways: Lost Deal Value: When the wrong rep works a deal alone because they're protecting their turf, you lose the collective expertise that could close bigger opportunities. Relationship Damage: Customers get confused when multiple reps approach them without coordination, making your organization look disorganized and unprofessional. Top Performer Exodus: Your best salespeople get frustrated with the politics and infighting, leading them to seek opportunities at companies with better team cultures. The companies that figure this out win big. The ones that don't hemorrhage talent and revenue to organizations that actually know how to build high-performing sales teams. The Solution: Strategic Commission Pools and Clear Ownership For Kayla's HOA challenge—and similar overlapping territory situations—here's the framework that actually works: Assign Relationship Ownership: The rep with the core relationship (the HOA headquarters contact) owns account retention and expansion. They're responsible for keeping that account long-term and get compensated accordingly. Create Local Opportunity Roles: Local reps in each territory focus on building relationships with on-site contacts—facility managers, groundskeepers, community center staff. They get compensated for new project acquisition and spot opportunities within their geographic area. Implement Commission Pools: Instead of fighting over who gets what percentage, create a commission pool for each major account. The pool gets divided based on roles and contributions, not territorial claims. Force Up-Front Agreements: Here's the crucial part: Make involved parties agree on commission splits before any work begins. Post-deal disputes are exponentially harder to resolve than pre-deal agreements. The Leadership Mindset Shift
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    19 分