WINNING AT SELLING

Bill Hellkamp
  • 4.6 (118)
  • Management
  • Updated Weekly

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 projecting a positive attitude. Whether you are defending first place in the market or dedicated to fighting for first place, each episode will deliver proven advice you can apply that day to improve your sales results.

  1. 4d ago

    #720 - I Fell Into Sales...Now What? - 10/9/2026

    Did you choose sales or did sales choose you? Stefani ran a LinkedIn poll. Nearly half of 496 people said they fell in. If that's you, this episode is going to hit differently. Because falling in is fine. Staying lost? That's a choice.". Structured Sales Process Implementation Stefani and Bill discussed the importance of having a structured sales process rather than relying on untrained "accidental salespeople" who wing it without a clear methodology. Stefani emphasized that a sales structure doesn't make you less human but actually frees you up to be more present and confident in conversations, while Bill shared insights about how poor processes can lead to lost sales opportunities when salespeople lose control of the conversation. They agreed that structure doesn't require throwing out existing successful patterns but rather adding a framework that allows for flexibility and adaptation when things don't go as planned. Golden Nugget: "Plans are useless, but planning is indispensable." — Dwight D. Eisenhower Resources: Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: www.reachdev.com Stefani Havel LinkedIn:  linkedin.com/in/stefanihavel Stefani Havel Website: www.stefanihavel.com

    #720 - I Fell Into Sales...Now What? - 10/9/2026

  2. 4d ago ·  Bonus

    You Might Also Like: The Oprah Podcast

    Introducing Why Is America Different Than Every Other Country When It Comes to Guns? from The Oprah Podcast. Follow the show: The Oprah Podcast BUY THE BOOK!  The American Way of Killing by Malcolm Gladwell ⁠https://amzn.to/4jvQMuE⁠  Malcolm Gladwell - one of America’s foremost thought leaders - examines our country’s obsession with guns and the devastating toll gun violence has taken on our communities. In his new book, The American Way of Killing: The Invention of an Epidemic, Malcolm challenges some of our most deeply held beliefs about American gun violence: what we’re missing about the root cause of most violence, how modern medicine is obscuring the reality of the problem, why the answer might be more police—not less—and how we’ve lost sight of the historical context surrounding the Second Amendment. Oprah and Malcolm speak with a Chicago based E.R. doctor who lost 15 close friends and family members to gun violence. He teaches students as young as fourth grade how to treat a gunshot wound. This episode also offers some common sense solutions to a seemingly intractable problem. 00:00:00 - Welcome Malcolm Gladwell, author of “The American Way of Killing” 00:04:20 - European vs. American police 00:08:50 - Stats around more police 00:09:50 - Malcolm’s experience with guns 00:13:30 - Welcome Dr. Pratt 00:16:33 - Talking to kids about gun violence 00:19:15 - Changing gun violence 00:21:00 - Treating gun shot wounds 00:25:13 - The 2nd amendment 00:29:00 - Crime vs. violence 00:33:45 - Instrumental vs. expressive violence 00:40:00 - Are we learning from our mistakes? 00:43:00 - The gun problem is not unsolvable Follow Oprah Winfrey on Social: ⁠https://www.instagram.com/oprahpodcast/⁠⁠ https://www.facebook.com/oprahwinfrey/ DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to team@podroll.fm.

    You Might Also Like: The Oprah Podcast

  3. Oct 2

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

    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 Success in Selling." He explained that the assistant buyer posture involves coming alongside clients to help them make decisions rather than pushing products, focusing on building trust and partnership rather than just being a "trusted advisor." Bill shared examples from Carnegie's work and Boettcher's book to illustrate the effectiveness of this approach, including the concept of getting physically or verbally aligned with prospects to build better connections. Client Partnership Building Strategies Jimmy and Bill discussed strategies for building partnerships with clients rather than treating sales as a transactional process. They emphasized the importance of using language that positions the client as having already made a purchase decision, sitting alongside rather than above clients during discussions, and asking questions to help clients reach conclusions on their own. The conversation included practical advice about physical positioning during client meetings and the importance of focusing on solving client problems rather than using sales techniques that feel manipulative. Golden Nugget: "A salesperson cannot know too much, but he or she can talk too much." Frank Bettger – Author of How I Raised Myself from Failure to Success in Selling Resources: Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: reachdev.com Jimmy Z LinkedIn: linkedin.com/in/jimmyzugschwert Jimmy Z Website: JimmyZSpeaks.com

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

  4. Sep 25

    #718 - Stop the Sales and Marketing Disconnect - 9/25/2026

    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 the relationship between sales and marketing teams, highlighting how poor communication and silos can lead to misaligned strategies and missed opportunities. They emphasized the importance of regular, open communication between sales and marketing teams, using an example of a successful salesperson named Marty who actively engaged with the marketing team to achieve better results. John stressed the need for alignment from the beginning and the value of sales feedback in shaping consistent brand messaging, while Bill noted the disconnect that can occur between director-level decisions and actual sales experiences on the ground.   Sales and Marketing Alignment Discussion Bill, John and Beau discussed the challenges of alignment between sales and marketing teams, particularly how different perspectives can emerge between management and front-line staff. They explored how marketing can effectively support sales by creating familiarity and pre-qualifying prospects before sales conversations, with Beau emphasizing the importance of understanding customer experiences and needs. The discussion concluded with insights about how modern marketing must adapt to the "zero click era" by creating valuable content that can be discovered through AI and large language models, with Bill recommending OrangeBall Creative as a resource for companies in the Midwest area. Golden Nugget: "If sales and marketing are telling different stories, the customer gets to decide which one to believe." Resources: OrangeBall.ai – Self-directed, AI enhanced marketing and branding services Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: reachdev.com Bill Hellkamp email: Bill.Hellkamp@reachdev.com

    #718 - Stop the Sales and Marketing Disconnect - 9/25/2026

  5. Sep 18

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

    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 customer has moved into the reasoning stage of the buying cycle. He emphasized that salespeople should resist the urge to immediately go into sales mode and instead allow the prospect time to think and consider the information presented. Bill agreed with this approach, referencing a previous episode with Erik Thurwanger about The Ponder Principle and emphasizing the importance of letting prospects think without filling silence with unnecessary talk. Customer Pause Sales Strategies Erik and Bill discussed strategies for handling customer pauses during the sales process, focusing on the four-step buying cycle and how to address customer hesitation in the reasoning stage. They explored techniques for uncovering objections, including asking questions about concerns and presenting customers with two clear options: either the solution hasn't been fully developed or the price point isn't where the customer hoped it would be. Bill emphasized the importance of not automatically dropping prices and suggested that salespeople should better address the "why, now, and why you" questions that customers naturally ask.  Golden Nugget: "If you want to go fast go alone, if you want to go far go together." African Proverb Resources: Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: reachdev.com Bill Hellkamp email: Bill.Hellkamp@reachdev.com Erik Haugen LinkedIn: linkedin.com/in/erikrhaugen Erik Haugen Contact: erik@propcoachingandconsulting.com PROP Coaching and Consulting website: www.propcoachingandconsulting.com

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

  6. Sep 11

    #716 – Why Prospects Ghost You: Interest Isn't Commitment - 9/11/2026

    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 challenge of prospects "ghosting" after showing initial interest. They identified several key reasons for this phenomenon, including lack of trust built during the sales conversation, failure to understand the prospect's true needs, and insufficient qualification of opportunities. The discussion emphasized the importance of asking the right questions to uncover decision-making processes and gain genuine commitments rather than sending proposals without proper follow-up or meeting arrangements. They concluded by encouraging salespeople to reflect on four key questions before leaving prospect meetings: whether trust was established, if there's a real reason for change, understanding the decision process, and securing actual commitments for next steps. Golden Nugget: "The quality of your life is a direct reflection of the quality of the questions you are asking yourself." — Tony Robbins   Resources: Brian Maas LinkedIn: linkedin.com/in/brianmaas Brian Maas Contact: brian@intentionalselling.com Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: www.reachdev.com

    #716 – Why Prospects Ghost You: Interest Isn't Commitment - 9/11/2026

  7. Sep 4

    #715 - The Identity Problem: Why Talented People Underperform in Sales - 9/4/2026

    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 public speaking, noting that fear often stems from past negative experiences, and described how he helped students overcome these fears by reviewing their videos positively to create new, more positive mental associations. Sales Course Visualization Techniques Stefani discussed her eight-week sales course that focuses on mindset and identity before covering the sales process, emphasizing the importance of addressing mental barriers first. She explained her teaching on visualization techniques where salespeople close their eyes before sales calls to envision positive outcomes, which she described as rewiring the brain through neuroplasticity. Stefani used the analogy of water flowing around rocks to illustrate how consistent visualization can create new neural pathways. Overcoming Sales Mental Blocks Bill and Stefani discussed three steps for overcoming sales mental blocks: removing emotion from failures, identifying smallest changes that could have made a difference, and inserting positive energy into negative situations. Stefani then presented on identity as a key factor in sales performance, explaining how talented salespeople underperform due to incorrect beliefs about themselves and their role as guides rather than pushy salespeople.   Golden Nugget: "Whether you think you can or you think you can't—you're right."-- Henry Ford   Resources: Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: www.reachdev.com Stefani Havel LinkedIn:  linkedin.com/in/stefanihavel Stefani Havel Website: www.stefanihavel.com Convert Guide: SalesStrategyNetwork.com/Convert

    #715 - The Identity Problem: Why Talented People Underperform in Sales - 9/4/2026

  8. Aug 28

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

    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 decision? Decision Collision in Sales Jimmy discussed the concept of decision collision in sales, explaining how pressures from companies to meet goals can conflict with serving customer needs. He described how sales professionals often face multiple directives that can distract from focusing on what customers truly need. Bill agreed with this perspective, sharing his experience with problematic commission and incentive programs that can lead salespeople to make unethical decisions to meet short-term goals rather than generate genuine new business. Sales Ethical Decision Framework Discussion Jimmy and Bill discussed the challenges sales professionals face when managing conflicting pressures between company goals and customer needs. They identified three key collision points: recommending solutions that benefit the company more than the customer, not fully representing product features and benefits, and omitting important information that could affect customer decisions. Jimmy presented a decision framework using the four Ws (who benefits, what is being chosen, why the recommendation is being made, and when it would be defensible) to help salespeople maintain ethical standards while meeting production goals. Golden Nugget: "In your daily interactions with others, you might think the question in everyone's mind is, Do I like you? but the more important question, and the question everyone is actually asking is, Can I trust you?" David Horsager, from his book, Trust Matters More Than Ever. Resources: Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: reachdev.com Jimmy Z LinkedIn: linkedin.com/in/jimmyzugschwert Jimmy Z Website: JimmyZSpeaks.com

    #714 - The Decision Collision - 8/28/2026
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4.6
out of 5
118 Ratings

About

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 projecting a positive attitude. Whether you are defending first place in the market or dedicated to fighting for first place, each episode will deliver proven advice you can apply that day to improve your sales results.

Information

  • Creator
    Bill Hellkamp
  • Years Active
    2011 - 2026
  • Episodes
    100
  • Rating
    Clean
  • Copyright
    © winningatselling.com
  • Show Website
    WINNING AT SELLING

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