WINNING AT SELLING

Bill Hellkamp
  • 4.6 (118)
  • Management
  • 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. 6d ago

    #723 - The Sales Leadership Gap with Kristie K. Jones - 10/30/2026

    AI isn't just changing the way we sell, it's changing the way we need to lead those that sell. Activity metrics are improving and sales are following and so we congratulate ourselves on innovative leadership. In reality the system isn't healthy and this is where experienced sales leaders are misinterpreting the situation. They are treating AI adoption as a workflow problem when it is really a leadership problem. AI Transformation in Sales Leadership The podcast focused on Kristie's upcoming book, *The Sales Leadership Gap*, and the impact of AI on sales leadership. Bill and Kristie discussed how AI is changing the sales profession, moving beyond simple tools like AI note-takers to research agents and strategy partners. Kristie explained that AI adoption is a leadership problem, not just a workflow problem, and that leaders must shift from "flying the plane" to a "control tower" perspective. She outlined four core competencies for sales leaders: systems thinking, workflow design, decision leadership, and accountability clarity. They also discussed the changing buyer's journey, where marketing may own the early discovery and demo stages, leaving sales to handle a "validation" stage with more informed buyers. Kristie emphasized the need for reps to use objective judgment rather than blindly copying AI output. The conversation also touched on the risks of using non-enterprise AI tools and the importance of AI fluency and skepticism for both reps and leaders. Golden Nugget:  "It's time for sales leaders and founders to stop flying the plane and get their a** in the control tower!" – Kristie K. Jones Resources: LinkedIN:  https://www.linkedin.com/in/kristiekjones/ YouTube:  https://www.youtube.com/@kristiekjones Website:  https://kristiekjones.com/ Bill Hellkamp LinkedIn: linkedin.com/in/billhellkamp Bill Hellkamp Website: reachdev.com Bill Hellkamp email: Bill.Hellkamp@reachdev.com

    #723 - The Sales Leadership Gap with Kristie K. Jones - 10/30/2026

  2. Oct 23

    #722 - Handling Objections 101 - 10/23/2026

    Sales Objection Handling Strategies Erik and Bill discussed strategies for handling customer objections in sales. They agreed that objections indicate customers are still reasoning through their decision and not rejecting the idea outright. Bill emphasized the importance of listening carefully to understand what customers really want and avoiding quick, canned responses. Erik shared a personal example of how effective questioning and empathy helped his sister make a decision about selling property. They concluded that the key is to make customers feel good about asking questions, clarify their needs, and present solutions that highlight what's possible while maintaining authenticity and quality. Golden Nugget: "An objection is not a rejection; it is simply a request for more information." — Bo Bennett 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

    #722 - Handling Objections 101 - 10/23/2026

  3. Oct 16

    #721 - Would You Hire You? Sales Interview Mistakes to Avoid - 10/16/2026

    Salespeople spend their careers convincing prospects to buy, but many struggle when it comes time to sell themselves in an interview. Drawing from years of interviewing sales candidates, we'll look at the red flags sales leaders notice, the mistakes even experienced salespeople make, and how to prepare for your next interview with the same discipline you would bring to an important sales call. Sales Interview Preparation Strategies Brian shared five key things salespeople should focus on before interviews to demonstrate their skills effectively. He emphasized the importance of knowing and explaining their sales numbers and success stories, preparing thoroughly about the company and role, taking appropriate control during interviews by asking relevant questions, bringing evidence to support claims rather than just making statements, and closing interviews by seeking commitments and next steps. Bill agreed with these points, particularly highlighting the value of preparation and respect shown through proper research and questioning. They discussed how these principles apply not just to job interviews but also to sales conversations with clients. Golden Nugget: "Success occurs when opportunity meets preparation." — Zig Ziglar Resources: Show Website: www.winningatselling.net 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

    #721 - Would You Hire You? Sales Interview Mistakes to Avoid - 10/16/2026

  4. Oct 9

    #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

  5. 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

  6. 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

  7. 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

  8. 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
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4.6
out of 5
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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
    99
  • Rating
    Explicit
  • Copyright
    © winningatselling.com
  • Show Website
    WINNING AT SELLING

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