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PODCAST

WINNING AT SELLING

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

business management

All Episodes

35:03

#719 - The Posture of Partnership - 10/2/2026

WINNING AT SELLING ·

2026/10/02

People don't like to be sold; they like to buy. Lasting relationships come from being a valued partner to your clients. Unfortunately, not all sales professionals see it this way. Many of them are transactional and just looking to close the next deal. But if you are a valued partner the deal doesn't close, the relationship opens. Assistant Buyer Success Strategies Jimmy discussed his approach to becoming an assistant buyer, inspired by Frank Boettcher's book "How I Raised Myself from Failure to

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36:23

#718 - Stop the Sales and Marketing Disconnect -...

WINNING AT SELLING ·

2026/09/25

Sales wants marketing to create demand, open doors, and make conversations easier. Marketing wants sales to take that momentum and turn it into revenue. But when the two teams operate in silos, sales ends up asking for things marketing never planned to create, while marketing creates things sales never uses. So how do we get sales and marketing working together in a way that actually helps both teams win? Sales-Marketing Team Alignment Challenges Bill, Beau and John discussed the challenges in

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38:01

#717 - Overcoming the Stall - 9/18/2026

WINNING AT SELLING ·

2026/09/18

You've made a great connection with your prospect, helped them identify their need and motivation, and guided them to a solution that makes sense for them only to run into hesitation. Today we get to unpack what your prospect's stall or objections are telling you and how to respond in a way that makes it easy for them to buy TODAY. Handling Sales Objections Positively Erik discussed how a pause or objection from a prospect during a sales process should be viewed as a positive sign indicating the

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38:28

#716 – Why Prospects Ghost You: Interest Isn't...

WINNING AT SELLING ·

2026/09/11

A prospect tells you the meeting was great, asks for a proposal, and seems genuinely interested. Then, they suddenly disappear! Ghosting isn't always a follow-up problem. Often, something was missed earlier in the sales process. We'll look at the difference between interest and real commitment, and the warning signs around trust, value, qualification, decision process, and next steps that salespeople may be overlooking. Sales Prospect Ghosting Solutions Bill and Brian discussed the common sales

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25:42

#715 - The Identity Problem: Why Talented People...

WINNING AT SELLING ·

2026/09/04

It's not skill. It's not knowledge. It's identity. When someone doesn't see themselves as a "salesperson," they unconsciously self-sabotage—underpricing, over-delivering before the sale, and avoiding the ask. Changing behavior without changing identity never sticks. Sales Failure Analysis Discussion Bill and Stefani discussed examining and learning from sales failures to identify mental blocks, with Bill emphasizing the importance of reviewing their processes. Bill shared his experience teaching

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33:39

#714 - The Decision Collision - 8/28/2026

WINNING AT SELLING ·

2026/08/28

In sales, there can be a wide variety of pressure points. You may have a customer that claims they just want the lowest price. Your company may be demanding you sell more of one product over another. How do these factors influence the decisions you make in selling? Are you more concerned about your needs or the needs of your customer? On today's episode, we will consider the following question: When the pressure to produce and the responsibility to serve the customer collide, what guides your

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31:49

#713 - Guest: Erik Therwanger - The Ponder Principle...

WINNING AT SELLING ·

2026/08/21

Although studies show that buying is an emotional decision, most salespeople tend to stay in the realm of logic. To move a prospect into emotional territory the seller needs to induce them to "think", to "ponder". And getting the prospect to ponder, can revolutionize your selling process. Causing Prospects to Ponder Erik and Bill discussed the importance of causing prospects to "ponder" rather than just hear or listen during sales presentations. Erik explained that when sales professionals make

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37:22

#712 - The Power of the Plan - 8/14/2026

WINNING AT SELLING ·

2026/08/14

Are you letting sales be done to you or are you planning and accounting for them so there are less surprises? With proper planning you can effectively have each quarter WON by the time it starts instead of waiting to see what happens at the end! Golden Nugget: "By failing to prepare you're preparing to fail." Benjamin Franklin Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: reachdev.com Bill Hellkamp email: Bill.Hellkamp@reachdev.com Erik Haugen

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28:42

#711 - Why Every Great Sales Meeting Starts with an...

WINNING AT SELLING ·

2026/08/07

One of the simplest things salespeople can do to improve their meetings is also one of the most overlooked: a well-planned agenda. In less than two minutes, you can establish credibility, show you're prepared, involve the prospect in shaping the conversation, and set expectations for what happens next. The agenda isn't just about organizing a meeting, it's about earning the right to lead it. Golden Nugget: "Success is nothing more than a few simple disciplines, practiced every day." ~ Jim Rohn

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31:32

#710 - The Follow-Up is the Sale - 7/31/2026

WINNING AT SELLING ·

2026/07/31

Most salespeople quit after one or two touches. But research says most decisions happen after five to twelve. This episode is about what to say on follow-up #3, #5, and #7. How do you add value instead of "just checking in". Sales Follow-up Strategies Discussion Stefani discussed the importance of effective follow-up in sales, emphasizing that it's not about being pushy but about serving the client by staying relevant, adding value, and deepening trust. She shared a structured follow-up

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28:50

#709 - Establish a Connection Right Away and the...

WINNING AT SELLING ·

2026/07/25

As a salesperson it's easy to get excited about your product or service. So much so that you can find yourself explaining about the great benefits before you even know much about the prospect. In essence, we want to tell our story before we listen to their story. Instead, resist the urge to tell and allow their stories to guide you to a valuable solution. Active Listening in Sales Techniques Jimmy discussed the importance of active listening in sales, emphasizing the need to listen to

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35:32

#708 - Guest: Steve Keating – Turning a Great...

WINNING AT SELLING ·

2026/07/17

The sales profession can be a very lucrative career. You can grow a client that buys regularly and provides a hefty commission. Or you might be a hunter who is especially suited to developing new clients which might pay even better. No matter which type of sales professional you are, you likely measure your success by how much you make; but the top sales professionals measure their success by how much of that money they are able to keep. In this episode Bill Hellkamp welcomes sales leadership

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41:22

#707 - Are you making it easy for your customer to...

WINNING AT SELLING ·

2026/07/10

Are you making it easy for your customer to buy? The job of Sales, in its simplest form, is to ask, say, and do things that make it easy for your prospect to say yes to your product/service/solution TODAY! Yet, it seems that some salespeople blather on about features long before they know which ones really connect with the prospect. In sales cultures that are so focused on selling we are being counterintuitive to why people buy! Telling is selling and people don't like being sold but they love to

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27:22

#706 - Your Prospect Isn't the Final Decision...

WINNING AT SELLING ·

2026/07/03

Have you ever finished what you thought was a great sales call only to hear, 'This looks good, but I need to run it by my boss?' Most salespeople breathe a sigh of relief because they think the deal is still alive. Sometimes it is. But what usually happens is you've just been removed from the most important part of the sales conversation." In this episode, Bill is joined by guest host, Brian Maas. They discuss winning strategies and key questions to avoid getting trapped by a prospect who needs to

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31:56

#705 - Stop Winging It. Start Winning! - 6/26/2026

WINNING AT SELLING ·

2026/06/26

Most salespeople who struggle with confidence think it's a personality problem. It's not. It's a structure problem. When you don't know what comes next, your brain fills the gap with anxiety, and that anxiety shows up as hesitation, over-explaining, or caving on price. Here's what I want every listener to hear: confidence is not something you either have or you don't. It's not a personality type. It's not a gift some people are born with. Confidence is manufactured, through preparation,

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38:00

#704 - How to Have a Great First Meeting - 6/22/2026

WINNING AT SELLING ·

2026/06/22

The first time we meet with a prospect is exciting and challenging. The whole opportunity waits for us to uncover it. But it is also fraught with dangers. Will we get along? Do we have a solution that meets their needs? Will I be able to understand the core issues the prospect needs to solve? This is such a valuable topic, because we all want to get started on the right foot in our first meeting with a new client. More than just a great first impression, we want to make a real connection. Over my

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32:10

#703 - A Tribute to Scott "The Professor" Plum -...

WINNING AT SELLING ·

2026/06/16

On Tuesday January 13, 2026, Scott "The Professor" Plum, my good friend, business partner and the co-host of the Winning at Selling podcast died suddenly. After 5 years and over 300 weekly conversations a great advocate for the selling profession went silent. In this episode I attempted to find some of the fun and interesting conversations and diatribes that give the best profile of what he believed and stood for.

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33:23

#702 – Why Discipline Beats Distraction Every Time -...

WINNING AT SELLING ·

2026/01/08

January has a way of forcing clarity. Some people lean into that through Dry January, which is about far more than alcohol. It's about recognizing the distractions we use to numb discomfort, delay discipline, and avoid our best work. In sales—and in life—success rarely breaks down because of a lack of talent. It breaks down because distractions keep winning. Today's conversation focuses on how discipline allows us to control ourselves, influence others, and make a meaningful difference. If you're

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35:19

#701 – The Value of Ranking Your Customers

WINNING AT SELLING ·

2026/01/02

Not all customers are created equal—and treating them as if they are is one of the most common and costly mistakes organizations make. Companies often pride themselves on "great service for everyone," yet fail to recognize that limited resources require intentional allocation. Consider how you might categorize your companies service philosophy as Scott and I discuss The Value of Ranking Your Customers and other terrific tidbits on Episode 701 of the Winning at Selling podcast. Johnny Franchise -

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35:57

Dec 2025 - Ten Greatest Selling Questions

WINNING AT SELLING ·

2025/12/26

Welcome to show number 700! For Bill and me this is show #300. Every week for the past 5 years, 8 months and 24 days Bill and I have worked to deliver the latest sales advice, strategy and tactics so you can win at selling. Asking the right questions is a key capability of the sales professional. So let us answer your questions with our questions as Bill and I reveal the Ten Greatest Selling Questions and other incredible information on Episode 700 of the Winning at Selling Podcast. Handout:

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