Best Salesstrategies Podcasts (2025)

1
Embracing Remote Work: How Founders Build Freedom & Output 33:33

10h ago33:33

33:33

In this episode of Build Your Business: From Fear to Freedom, Matt Reynolds and Chris Reynolds dive deep into the powerful benefits of embracing remote work—and why they’ll never return to a traditional office setup. From unlocking personal freedom to building high-performing teams across time zones, remote work isn’t just a lifestyle change—it’s a…

1
Apr 2025 - Gaining Wallet Share from Current Clients 35:45

4h ago35:45

35:45

Is it better to prospect for new customers or get more business from our current clients? I don’t think one is necessarily better than the other, but it is certainly cheaper and should be easier to get business from those to whom we are already providing services. Unfortunately, those customers often get pushed off on delivery while the sales team …

1
Everyday Leads: How to Generate New Opportunities Without Burning Out 16:24

1h ago16:24

16:24

Bill introduces his concept of "Everyday Leads" - a framework for consistently generating new business opportunities through leverage rather than labor. He explains why traditional cold calling burns people out and introduces five key elements you need to implement an effective lead generation system: proper market positioning, clear external probl…

1
Apr 2025 - Define Yourself 32:06

10d ago32:06

32:06

During every election season, we see candidates rushing to define themselves in the view of their voter — before their opponent gets the chance. Why? Because the first impression often sticks. It becomes the lens through which everything is viewed. But let me ask you this: Who’s defining you? Is it your customers? Your coworkers? Your critics? Or i…

1
The Power of Thinking Time to Unlock Founder Potential 37:20

7d ago37:20

37:20

Quiet reflection might be the most powerful leadership tool you're not using. In this episode of Build Your Business, Matt and Chris explore how "thinking time" fuels strategic clarity, innovation, and sustainable leadership. Unlocking Founder Potential Starts with Thinking Time Intentional solitude creates space to lead, not just operate. Thinking…

1
The 2X Roadmap: 10 Habits of High-Performers (Part 2) 15:34

6d ago15:34

15:34

In this follow-up episode, Bill completes his breakdown of the 10 strategies that can double your business growth. Building on last week's fundamentals, Bill reveals five additional habits that separate top performers from the rest. These insights come directly from Bill's observations of million-dollar performers. Whether you're a sales profession…

1
Overcoming Founder Isolation: Break the Cycle of Overwork & Anxiety 41:29

17d ago41:29

41:29

Feeling like you’re carrying the entire business on your shoulders? You’re not alone. In this vulnerable episode of Build Your Business, Matt and Chris talk openly about the emotional weight of being a founder—and how to break free from the loop of overwork, anxiety, and isolation. 1. What Founder Isolation Really Feels Like More than being alone—i…

1
Apr 2025 - Special Guest - Pete Steege 33:58

13d ago33:58

33:58

Sales and marketing should work together closely to craft messages that engage customers and encourage them to consider a product or service. Unfortunately this is not always true! Quite often marketing is more interested in winning awards and sales doesn’t pay attention to the messages that marketing is sending out. This results in confused prospe…

1
The 2X Roadmap: 10 Habits of High-Performers (Part 1) 12:33

14d ago12:33

12:33

In this episode, Bill shares the first five habits that separate top sales performers from the rest. Recorded from a live client session, Bill reveals key strategies that can help you double your business growth. These actionable strategies come directly from Bill's observations of high achievers in the field. Tune in next week for Part 2, where Bi…

1
The Art of Sales Without the "Sales Tactics" 58:17

24d ago58:17

58:17

Sales doesn't have to feel sleazy or scripted. In this episode of Build Your Business, Matt and Chris Reynolds explore how to master the art of sales by being authentic, problem-focused, and client-centered. The Power of Authenticity in Sales The best salespeople lead with honesty and care. Build trust through real, meaningful conversations. Focus …

1
Apr 2025 - Who Defines the Marketplace? 31:22

20d ago31:22

31:22

Remember your first day on the job—full of enthusiasm, optimism, and ambition. But over time you start to become defeated and start to lose that initial drive. We start to make excuses and sell them up to leadership. Maintaining success requires a daily commitment to optimism, proactive beliefs, clear objectives, and intentional behaviors. Manageme…

1
The O-O-O-E Storytelling Framework 7:31

21d ago7:31

7:31

Tired of complicated storytelling advice with no practical framework? In this episode, Bill shares his straightforward O-O-O-E method for business storytelling that anyone can use right away. Learn how to craft compelling stories using three key observations followed by one powerful epiphany that resonates with potential clients. Bill illustrates t…

1
Apr 2025 - Special Guest Mike Weinberg - 5-year Anniversary Show 48:56

28d ago48:56

48:56

Thank you for joining us on this SPECIAL 5th ANNIVERSARY EPISODE of the Winning at Selling Podcast. I’m Professor Scott Plum of the Minnesota Sales Institute and with me is Bill Hellkamp of REACH Development Systems Sales managers have a tough job. Pressure from upper management to increase sales. Handling customer problems that have escalated. And…

1
Questions To Transform Your Sales Process 12:59

1M ago12:59

12:59

In this episode, Bill shares his proven method for starting new client engagements - a strategic 20-question assessment that identifies sales performance gaps and growth opportunities. Whether you're a VP of Sales, CEO, or frontline salesperson, these diagnostic questions help pinpoint exactly where your sales process needs improvement. Bill walks …

1
Mar 2025 - Why Enter it into the CRM? 36:50

1M ago36:50

36:50

How many conversations can you keep track of in your head? How about with your files on your desk? What about your notebook or journal? Maybe 3? That’s too low. You're not alone — I struggle with this too! How do we determine what is most important today? What do you want to be known for by our customers, clients, and colleagues? How can we reduce …

1
10 Strategies to 2X Your Revenue 13:59

1M ago13:59

13:59

In this episode, Bill Cakey shares 10 proven strategies that have helped his high-achieving clients (those earning $150K-$500K annually) double their revenue and increase their market impact. Bill walks through each strategy in detail, from crafting a compelling personal and corporate story to developing an economic philosophy that shifts conversat…

1
Mar 2025 - Top 5 Negotiating Skills for Salespeople 40:09

1M ago40:09

40:09

At the end of most proposal or quote presentations there is the chance of a negotiation breaking out. Being unprepared is not a good option and will probably prompt an unplanned reaction such as a price reduction. The professional salesperson is prepared and ready to respond, saving the sale and maintaining profitability. You’re going to have to sh…

1
The Modern Seller's Mindset: 5 Mental Shifts for Success 12:04

2M ago12:04

12:04

In this episode, Bill shares five powerful mindset shifts that can transform your sales performance in today’s rapidly changing marketplace. Drawing from his exclusive monthly Insider group sessions, Bill reveals half of his coveted “10 Mindsets” framework that helps sales professionals, CEOs, and entrepreneurs excel at customer acquisition. He exp…

1
Mar 2025 - Don't Be a Sales Jerk 32:48

2M ago32:48

32:48

We’ve all met a creepy salesperson. Someone who, after our conversation, makes us feel like taking a shower. They are slimy and dishonest. Self-interest oozes from every pore and every statement is taken with caution. They don’t need a checkered sport coat and gold chains – they advertise their insincerity with their opening handshake. We hope this…

1
Mar 2025 - Special Guest Peter Beaumont 33:05

2M ago33:05

33:05

Business owners often feel overwhelmed, struggling to focus on their true passions while distractions pull them away from their goals. Breaking free from this cycle is difficult alone—and finding a skilled, supportive team can be just as challenging. So, who can help? Join Bill and me as we welcome back Peter Beaumont to explore practical strategie…

1
Building Your Sales Engine 13:35

2M ago13:35

13:35

In this episode, Bill challenges the traditional labor-dependent approach to sales growth and introduces his framework for building a sustainable sales engine. He explains why relying solely on personnel leads to inconsistent results, forecasting difficulties, and vulnerability to staffing changes. Instead, he presents a paradigm shift: “You don’t …

1
Feb 2025 - Seven Assumptions 31:16

2M ago31:16

31:16

Our perception of a situation is shaped by past experiences, judgments, beliefs, and biases. These elements mixed, each weigh differently, to form our unique perspective. No two people see reality the same way. But is our perception of reality true? It’s real—yes. No one can take away your reality. However, what’s real may not always be true. This …

1
Crafting Your Signature Story: A Framework for Authentic Connection 19:31

2M ago19:31

19:31

In this episode, Bill shares a comprehensive framework for developing your signature story that resonates with prospects and customers. Through his own personal journey from struggling salesperson to successful sales coach, Bill breaks down the essential elements of compelling storytelling: situation, challenge, desire, decision, breakthrough, and …

1
Feb 2025 - Quote Versus Proposal 34:48

2M ago34:48

34:48

A customer calls and asks you to send them a quote. Do you do it or do you ask for an appointment to find out more about their needs? If I just send over a quote, how can I be sure that it will really address their issues? But is a full blown proposal really necessary and will it help or hurt my chances to make the sale? What’s a salesperson to do!…

1
Feb 2025 - Special Guest Scott Welle 31:48

3M ago31:48

31:48

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…

1
The Joy of Selling: 5 Ways to Remove the Struggle from Sales 17:22

3M ago17:22

17:22

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…

1
Feb 2025 - The Weekly Sales Meeting 35:26

3M ago35:26

35:26

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…

1
Jan 2025 - Uncovering Your Prospect's Expectations 32:28

3M ago32:28

32:28

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…

1
Revenue Mastery (Part 3 of 3) 7:19

3M ago7:19

7:19

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 …

1
Jan 2025 - Special Guest Steve Keating on Ethics in Selling 36:17

3M ago36:17

36:17

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…

1
The Key Interactions (Part 2 of 3) 7:15

3M ago7:15

7:15

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…

1
Building the Foundation (Part 1 of 3) 8:03

4M ago8:03

8:03

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 …

1
Jan 2025 - The Hiring Process 34:24

4M ago34:24

34:24

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…

1
Jan 2025 - 5 Ways to Jump Start the New Year 36:01

4M ago36:01

36:01

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 …

1
Dec 2024 - Special Guest Frank Gustafson 35:06

4M ago35:06

35:06

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…

1
Dec 2024 - How to Leverage the Buyer’s Journey 37:06

4M ago37:06

37:06

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…

1
Your First 3 Moves in 2025 7:58

4M ago7:58

7:58

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…

Podcasts Worth a Listen

Salesstrategies Podcasts

Podcasts Worth a Listen