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 ...
Sep 16, 2025•14 min
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 Sept. 10, 2025, Charlie Kirk was fatally shot while addressing an audience at Utah Valley Universit...
Sep 14, 2025•12 min
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 cla...
Sep 11, 2025•37 min
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...
Sep 09, 2025•20 min
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 tomorr...
Sep 04, 2025•32 min
A 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 p.m., 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 ...
Sep 02, 2025•9 min
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 tea...
Aug 28, 2025•23 min
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 s...
Aug 26, 2025•19 min
Sales activity is the lifeblood of your career. But for too many salespeople, it’s the very thing holding them back. You’re generating a ton of activity, your calendar is packed, your inbox is overflowing, and by the end of the day, you’re drained. But your numbers aren’t moving. You’re not gaining ground; you’re just driving in circles. As Ron Karr, author of Velocity Mindset , says, the difference between amateurs and top performers isn’t how fast they move, but whether they’re moving with a c...
Aug 20, 2025•40 min
Here’s a question that’ll flip your understanding of cultural intelligence in sales upside down: How do you win over a room full of skeptical Spanish teenagers when you’re the obvious American outsider who barely speaks their language? That’s exactly what Spencer Birmingham from Arkansas faced when he called into Ask Jeb. Fresh out of college with a marketing degree and an internship at International Paper under his belt, Spencer was heading to Spain for eight months as a language teaching assis...
Aug 19, 2025•21 min
In today’s economy, being the account manager who keeps clients happy and renewals steady simply isn’t enough. Every budget line item is under the microscope. Customers want proof of ROI, so you have to show measurable value while driving growth. Reva Pellerin, the #1 enterprise account manager at Vidyard, puts it bluntly: “If you simply renew your book of business at 100%, that’s not your target. Your target is to grow the customer base.” The best account managers aren’t just order-takers. They...
Aug 14, 2025•35 min
Overcoming call reluctance starts with understanding why even seasoned sales pros freeze up when it’s time to pick up the phone. They’re paralyzed by one simple fear: interrupting a prospect’s day. That’s exactly what Kirk Roberts from Richmond, Virginia, brought to the table. Kirk’s problem wasn’t about not knowing what to say or how to pitch—it was the mental block around the very idea of interruption. He hated being interrupted by low-quality sales calls himself. And even though 99% of the ti...
Aug 12, 2025•18 min
In 1960, two brothers scraped together $900 and bought a failing pizzeria in Michigan, launching what would become a cautionary tale about sales incentive programs gone wrong. Within months, one brother traded his half of the business for a beat-up Volkswagen, leaving Tom Monaghan alone with his ambitions. By 1965, with three stores under his belt, Tom faced a naming crisis. He couldn’t legally keep using the original name, DomiNick’s, so an employee suggested “Domino’s.” The logo? Three dots, o...
Aug 11, 2025•14 min
The transition from closer to coach is where most new sales leaders struggle. You’ve put in the work, made the calls, and closed the deals. Your numbers speak for themselves. You were the rainmaker. The top dog. The one everyone pointed to as the example of what a salesperson should be. Finally, you’ve earned the promotion you’ve been chasing: Sales Manager. The very habits that made you successful as a top-performing rep (moving fast, working independently, and ignoring administrative tasks) ca...
Aug 07, 2025•31 min
Here’s a question that’ll drive you absolutely crazy: How do you sell professional services without giving away everything for free? That’s the burning question from Laura and Adam, attorneys who are struggling with the classic professional services dilemma. Their intake team and attorneys want to showcase their expertise by giving away everything for free during sales conversations. Meanwhile, they’re also trying to figure out what kind of salesperson they need to hire to sell high-value legal ...
Aug 05, 2025•14 min
If you’re only showing up in one place, you’re not showing up at all, which is why top sales reps are making multi-channel prospecting a priority and leveraging LinkedIn to get ahead. “The reality of buying and selling is that everyone has different preferences, and as a salesperson, we need to use as many tools as possible. If you are only making calls or sending emails, you’re missing [prospects] that don’t answer calls or reply to emails,” says Daniel Disney, one of the world’s leading social...
Jul 30, 2025•41 min
Should you use sales scripts to close more deals? That’s the question I get from salespeople who are struggling to hit their numbers and looking for that magic bullet that’ll transform their results overnight. They want to know if there’s a perfect set of words that’ll make prospects say yes every time. Here’s my answer: No. Not just no, but hell no. If you’re using scripts, you’re using a crutch that’s actually crippling your ability to build the one thing that closes deals: trust. And worse, y...
Jul 24, 2025•12 min
You know the feeling. You’re mid-pitch, and you watch your prospect’s eyes glaze over—their mind somewhere else entirely. It’s exhausting, demoralizing, and it’s killing your close rate. But what if you didn’t have to push so hard? What if you could create the kind of pull where prospects actually leaned in and said, “How do I get started?” In this episode of the Sales Gravy podcast, high-performance coach Kristin Andree shared her perspective: “If we put ourselves out there and let people know ...
Jul 24, 2025•29 min
Here’s a scenario that’ll hit close to home: What do you do when you were crushing your numbers just months ago, but now you can’t seem to close anything and your confidence is in the gutter? That’s exactly what happened to Dhruv, a business development rep from Saint Louis. After figuring out his rhythm in Q1 and hitting strong performance numbers, he found himself in a two-month slump with low attainment and shattered confidence. If you’re nodding your head right now, you’re not alone. Every s...
Jul 22, 2025•14 min
Will AI steal your sales team’s jobs? It’s the question haunting every sales floor conversation and keeping leaders up at night. But here’s the crucial insight: The biggest threat to your team’s sales careers lies in misinterpreting AI’s role. While the debate rages over robots replacing salespeople, forward-thinking organizations are already embracing “Agentic AI.” This isn’t your typical automation that just speeds up email sequences. It’s a completely different approach that turns AI into you...
Jul 17, 2025•23 min
How can one comp plan mistake sabotage your sales team before they even start? That’s the challenge facing Adam and Laura from the Rossen Law Firm in Florida. After attending one of our Dallas workshops, they made the bold decision to transition to a non-attorney sales team. Six weeks later, they’re all in on the strategy but hitting a wall on one critical issue: compensation structure. The problem? Like most law firms making this transition, they’re stuck in the traditional legal mindset when i...
Jul 15, 2025•12 min
How many times do you actually attempt to reach out to a prospect before you give up? On the Sales Gravy Podcast, Jessica Stokes calls out a common sales reality when prospecting: “We all know the average salesperson typically stops after three, maybe four attempts before moving on. We assume they’re not interested. We want to find a juicier lead.” This common behavior defines The 3-Call Fallacy—the flawed belief that if someone doesn’t respond after a few tries, they’re not interested. It’s whe...
Jul 10, 2025•52 min
Here’s the hard truth about social media for sales: You’re already behind, and it’s going to be a grind. That’s the reality Margarita from Dallas discovered when she called into our podcast. She’s a seasoned realtor with 20+ years of experience, built her entire business on referrals and warm market relationships, and suddenly realized she needs to master social media to stay competitive. Sound familiar? You’re not alone if you’re staring at this digital mountain wondering how the hell you’re go...
Jul 08, 2025•16 min
You think you’re being helpful. Your clients think you’re being annoying. Early in his career, Justin Goldstein learned this lesson the hard way. He admits, “I thought that picking up the phone and calling a client to talk about almost everything was the right way to go. I personally hate communicating over email. I’d rather just talk to you and figure it out.” The reality hit hard: clients viewed his frequent outreach as a burden rather than a benefit. Weekly update calls meant to show dedicati...
Jul 03, 2025•22 min
Here’s a question that’ll keep you up at night: What do you do when your emotions are sabotaging your sales performance? That’s the exact challenge posed by Kurt O’Donnell and the sales team from Joyland Roofing in Lancaster County, Pennsylvania. They’re crushing it—doing $10 million in revenue with individual reps generating $2 million each—but they identified a critical weakness that could derail their ambitious goal of hitting $100 million in 10 years. Kurt put it perfectly: “We need to actua...
Jul 01, 2025•17 min
The second quarter of 2025 delivered some incredible conversations on the Sales Gravy podcast. From discipline strategies that separate winners from wannabes to the psychology of selling that most reps completely miss, here are the five most powerful insights that can transform your sales results immediately. 1. Focus on Activity, Not Outcomes The Problem: Most sales reps get discouraged when they don’t book meetings, causing them to change their approach daily. The Solution: Cynthia Handal , wh...
Jun 27, 2025•18 min
Here’s a question that’ll make your blood boil: Why do most sales leaders spend their pipeline reviews asking about dollar amounts and close dates while completely ignoring whether their reps actually have real deals? That’s the brutal reality I see in sales organizations every single day. Leaders are obsessing over MEDIC, BANT, and other qualification frameworks while their pipelines are stuffed with dead deals that will never close. Meanwhile, their forecasts are consistently wrong, deals keep...
Jun 24, 2025•15 min
Ben Hogan, who was arguably the greatest ball striker the game of golf has ever known, taught that if you wanted to improve your swing you should focus on the cause rather than the result. This was good advice for golfers and brilliant advice for sales professionals. Because in sales, if you want to sell more it pays to become obsessed over your behaviors, techniques and processes rather than your outcomes. Most Sellers Obsess Over Outcomes Most salespeople are focused on winning or losing indiv...
Jun 24, 2025•10 min
You know the drill. The quota clock is ticking, the pressure is mounting, and there’s that relentless urge for a quick win. Every sales professional has felt that impulse to rush the process, to push for the immediate “yes,” because, well, the numbers demand it. But here’s the tough question you need to ask yourself: What if that very pressure is actively sabotaging your long-term success? What if chasing the fast buck is actually costing you the lucrative, lasting relationships that define an e...
Jun 20, 2025•28 min
That’s the question every sales leader, CEO, and HR department is wrestling with as A I tools flood the market with promises to automate everything from prospecting to closing deals. Meanwhile, salespeople are panicking, wondering if their jobs are about to disappear to some algorithm that can write emails faster than they can type “Dear Valued Customer.” If you’re losing sleep over this, take a deep breath. The fear is real, but it’s also completely misplaced. Here’s the brutal truth: AI isn’t ...
Jun 18, 2025•17 min
