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WINNING AT SELLING

Bill Hellkamp and Scott "Professor Plum"

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Welcome to the Winning at Selling Podcast. Your hosts Bill Hellkamp and Scott “Professor Plum.” This podcast is dedicated to the overall success in the sales channel. From the CEO to the front line salespeople, every role must be aligned, trained and committed, every day to achieve the desired outcome. This is not done without a commitment to ongoing career development in learning market-relevant techniques, overcoming conceptual barriers, applying proactive and productive behaviors and proj ...
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Welcome to The Bill Caskey Podcast, the show for company leaders, sales managers, and salespeople who are looking to take their sales game to the next level. Join your host Bill Caskey, renowned sales coach and strategist, as he shares modern sales strategies and leadership tips that will help you grow your sales team and increase revenue for your business. Each week, Bill brings a variety of guest experts and shares real coaching scenarios from his work with sales teams, providing valuable ...
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Hope isn't a strategy on the battlefield or in the boardroom, yet so many salespeople hope they'll make the next sale. In Bulletproof Selling, we're bringing the best minds and selling systems together each week so you can create more impact and more income in your sales! For more free sales systems, make sure you visit www.bulletproofselling.us or follow us at https://www.linkedin.com/in/shawnrhodes/
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Welcome to High Impact Sales Podcast for leaders ready to transform their sales experience and scale their revenue with help, impact, and integrity. It’s time for you to discover YOUR unique identity and how to connect with your audience. Listen to the latest episode with your hosts, Natalie Jill and Sinclair Kennally.
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Peak performance isn’t luck—it’s a choice. Top sales professionals don’t just work harder; they work smarter, optimizing their mindset, habits, and energy to consistently win. Today we will discuss science-backed strategies to stay motivated, handle rejection, and operate at your highest level. You will also discover how to manage your energy, buil…
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In this episode, Bill challenges the notion that selling has to be a struggle. Inspired by Stuart Wild’s philosophy, Bill shares five transformative principles that can make selling not just easier, but more fulfilling. From detaching from outcomes to mastering curiosity, he reveals how modern sales professionals can shift from the outdated “convin…
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The weekly sales meeting can be an effective tool for your team or a boring waste of time. As a leader, you choose how the meeting will go and if it will have the effect you desire. But if you leave it to chance, chances are it will suck! Grab your agendas, as Scott and I discuss The Weekly Sales Meeting and other magnificent metrics on Episode 653…
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Have you ever had a misunderstanding with a prospect? They committed, signed the agreement, and you started working together—only to discover they had completely different expectations about what you’d be doing. These misunderstandings often stem from unclear conversations and clever agreements. When expectations and obligations aren’t explicitly d…
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In this conclusion to the Million Dollar Seller Roadmap series, Bill Caskey reveals the final three steps to truly maximize your revenue potential. Learn how to pour gasoline on your foundation and interaction strategies with these game-changing approaches: ✓ Landing Larger Accounts: Discover how to position yourself as a thought leader and create …
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Hollywood has made clear their opinion of sales professionals. From the hard driver on Glengarry Glen Ross to the dishonest philanderers of Tin Men to the spastic incompetence of Tommy Boy. People can’t help but be influenced by these depictions. But we must also recognize the part actual salespeople play in swaying opinion. Each time a salesperson…
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In Part 2 of this powerful revenue-scaling series, Bill Caskey reveals the crucial interaction stage of the Million Dollar Selling Method. Building on the foundation from Part 1, discover the three key steps that will transform how you connect with prospects and convert opportunities: ✓ Pipeline Building: Learn why cold outreach isn't your only opt…
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Want to dramatically scale your revenue in 2025? In this first episode of our three-part series, Bill Caskey breaks down the crucial foundation stage of the Million Dollar Selling Method. Bill shares the first three steps to transforming your sales approach: ✓ Million Dollar Mindsets: Discover the game-changing perspective of detachment and unlock …
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We’ve all experienced the hiring process—whether as the candidate or the future supervisor. It’s a pivotal time when every piece of information and observation can significantly shape both parties' futures. Today, we’re diving into one of the most crucial elements of building a successful sales team: hiring the right salesperson. For business owner…
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So here we are again – a NEW YEAR. And that gives us a feeling of a new start. Perhaps you already joined a gym or set a goal to lose a few pounds. Although the January 1st date is an artificial opportunity, there’s nothing wrong with using it as a time to renew ourselves. As a sales professional there are plenty of good habits that you need to be …
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We create fresh starts at different times of the year. For some, it’s January 1st, for others it may be the day after Labor Day. Regardless of when, a plan and process with passion are all necessary. Whether you're mapping out your career goals, focusing on personal growth, or chasing that fitness milestone, stay tuned as we explore common setbacks…
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If, as a salesperson, you find yourself trying to push a prospect into making a decision, you may be wasting your time. Perhaps you should consider that the person you hope to have as a customer has their own planned agenda. And if you try to force your agenda on them, you may lose the opportunity to move forward. So prepare to get customer centric…
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In this forward-looking episode, Bill Caskey shares three essential strategies to enhance your business outcomes in 2025. He emphasizes the importance of authentic communication in an AI-dominated landscape while drawing from his book "12 Bold Moves." The key strategies include: developing a clear A-to-B roadmap to guide customers from their pain p…
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What is the goal of the first meaningful conversation with a prospect? I often ask this question and the answer I hear the most is – I need to educate them on my products, my company and myself. Really? That’s the goal? I say there are other topics more important to discuss. Stick around, take some notes and be open minded, as Bill and I investigat…
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Selling and compassion. Do these two concepts really fit together? Should a sales manager be a compassionate leader and do they even have that capacity? These are interesting and difficult questions. If you want to find the answers, stay tuned as Scott and I welcome Dr. Andrea Hollingsworth award winning author to discuss, Can Compassion Fuel Sales…
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Covey stresses to begin with the end in mind. Does that apply to sales calls with prospects? You betcha. What is your plan for the first time you meet? Did you receive the outcome you wanted? What could you have done differently? What did you learn, what would you change? What would you not say? What did you forget to say? If you like these questio…
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In this episode, Bill Caskey reveals three powerful strategies to increase sales profitability without increasing workload. These profit amplifiers help sales professionals and business leaders leverage their existing assets more effectively. Key Points: Creating and following a 30-day action plan focused on key revenue-generating activities Design…
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We’ve all been told that people buy from people they like. So, many salespeople spend a lot of time developing a “likeable” personality. This can mean that when a customer tells them NO, they can take it as a personal rejection. Well, put away that crying towel as Scott and I discuss What to Do When You Get a No and other quisling questions on Epis…
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In a post-pandemic world where people are seeking life/work balance while experiencing a "new normal," feelings of emotional labor can arise in the workplace. This can lead to symptoms of anxiety, fatigue, stress and more. If you want to learn how to reduce or eliminate these symptoms - through the power of perspective and emotional grit… Stay tune…
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Famed psychologist William James once said, “Nothing is so fatiguing as the eternal hanging on of an uncompleted task.” And that really true isn’t it. We know that we should strive to get more accomplished but so often we find ourselves frustrated by an inability to get off our butts! Perhaps we just need some good advice. Don’t put this off any lo…
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Are your sales team's skills stuck in the past? In this episode, Bill reveals four critical modern sales capabilities that many teams are missing out on. He breaks down why video production, digital writing/social selling, digital assets for the buyer journey, and AI implementation are no longer optional skills - they're essential for sales success…
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In this episode, Bill shares three powerful strategies that helped one of his client companies double their revenue from $15M to $30M. Bill breaks down the importance of map building (both company-wide and individual), message refinement, and conversion rate optimization. He explains why great plans should focus on inputs rather than outputs, how t…
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Every sale or negotiation, someone must make the first move. Some think you should never go first, if that’s the case, how do you get what you want - if you don’t ask by going first. There is a way of starting off a sales conversation and negotiation by going first. If you want to get what you want, learn how to go first as Bill and I discuss, Who …
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How do you react when the pressure is on? When customers or your manager demand more than you are able to give? The chaos of life can move even the best of us to react rather than respond. And in today’s world life can easily get out of control. What can you do? Take a chill pill and listen in as Scott and I welcome trainer and keynote speaker Lena…
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In this episode, Bill shares his personal insights on why many of us "play small" despite having massive potential. Bill opens up about his own struggles with imposter syndrome and reveals five practical strategies to break free from self-imposed limitations. From embracing your divine purpose to treating physical fitness as a business strategy, li…
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In this entertaining episode, Bill Caskey speaks with content marketing veteran Erik Deckers about the plague of corporate jargon in today's business world. Deckers, owner of a content marketing agency and longtime humor columnist, shares his insights on why phrases like "let's double click on that" and "value prop" are undermining clear communicat…
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As the adage goes, “You don’t have a second chance to make a first impression.” Just like when you invite employees to join your team, you must onboard them the best way possible for everyone to be successful. Let’s set the bar high as Bill and me as we discuss, Successful Onboarding and other motivating material on episode 638 of the Winning at Se…
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A famous quote by Albert Einstein states, “We cannot solve our problems with the same thinking we used to create them.” According to my dad (and probably yours, “Hey kid, what doesn’t kill you makes you stronger.” Whatever the case, as professionals we will have to deal effectively with problems to be successful. So let’s find some solutions as Sco…
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Bill challenges the conventional wisdom that sales training alone is the key to success. He introduces a multi-faceted approach to achieving excellence in sales, covering crucial areas often overlooked by traditional methods. From the importance of strategic planning and mindset mastery to understanding marketing principles and honing communication…
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If you’ve ever had to step away from your sales desk for a vacation or family emergency, you know how stressful it can be to return. Overflowing in boxes in overdue tasks make it difficult to pick up the pieces and restart deal momentum. There is a way to ensure that your deals progress even when you can’t be there to sell, and that’s what we sat d…
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As sales professionals we are inundated with “how to” selling advice. There are hundreds of sales books in print and even more sales blogs and podcasts. For example, the Winning at Selling podcast has over 200 weekly shows spanning more than 4 years. But is all of this advice useful or even true? Decide for yourself by joining Bill and me as we wel…
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Many salespeople fall into the habit of being quick to respond to every prospect sentence or question. The best salespeople, however, take the time to pause and assess what the best response might be. To learn how we can leverage the power of the pause to move further in our sales conversations, we sat down with Jeanette Bronee, a culture strategis…
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We’ve all seen it. Perhaps it’s the baseball pitcher who gives up 5 runs in the 2nd inning and of the sudden his arm is too sore to continue. Or maybe it’s the marathon runner who sees that she is too far behind to win and suddenly comes up lame. These are examples of the loser’s limp, the athlete who exaggerates an injury when they are facing defe…
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In sales, time is the one resource we can’t create more of. Too many salespeople spend their days simply checking tasks off a list without assessing which tasks will get them to their goals the fastest. To learn how we can better prioritize our sales time, we sat down with Ben Fiechtner, CRO of Clari. He showed us how he guides his sales team to be…
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After you deliver the best presentation possible you receive a "think it over," This happens when a prospect, instead of making a decision during a sales conversation, asks for more time to consider the offer. This response can often signal hesitation, uncertainty, or the need for more information. It can also be a polite way of avoiding a direct "…
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In this episode, Bill delves into the often misunderstood world of lead generation. He challenges traditional cold-calling methods and introduces a fresh perspective on building meaningful connections with prospects. Bill breaks down three crucial levels of connection: the Acquaintance Connection, the Contribution Connection, and the Shared Experie…
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If you’ve ever had a hard time communicating the value of what you sell to potential prospect, you might want to look in the mirror. Sales people often struggle to convert prospects because they are speaking to the wrong types of buyers. To ensure we are targeting the right audience, we sat down with Dr. Yaniv Zaid, author of the 21st Century Sales…
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The great coach John Wooden said, “True leaders accept responsibility for the outcomes of their decisions and actions.” And leadership expert, John Maxwell stated that, “A leader who doesn’t take accountability for their actions is like a ship without a captain.” While we know that accountability is important, we don’t always know how to make it th…
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