The Sales Evangelist

Donald C. Kelly
  • 4.9 (264)
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I believe in doing BIG THINGS! You should be earning 6 figures easily as a sales rep. But chances are you are not...yet! Sales is the most important department in every company but many sellers are never taught how to effectively sell, much less how to earn their way to high-income status. My own career limped along until a company I worked for invested in sales training to help me succeed. Immediately afterward, I closed a deal worth 4X what the company spent on me and saw hockey-stick improvement in my performance. So I started a podcast to “Evangelize” what was working. Today I interview the world's best sales experts, successful sellers, sales leaders and entrepreneurs who share their strategies to succeed in sales right now: folks like Jeffrey Gitomer, Jill Konrath, Bob Burg, and Guy Kawasaki to name a few. They share actionable insights and stories that will encourage, challenge, and motivate you to hustle your way to top income status. If you’re someone looking to take off in your sales career and earn the income you deserve, hit subscribe and let’s start doing BIG THINGS!

  1. 6D AGO

    How to Unlock Your Earning Potential This Year

    Most sales outreach blends into the noise not because sellers lack effort, but because they approach prospects the same way everyone else does. In this episode, Ashley Winston breaks down why traditional outreach tactics fall flat and how sales professionals can stand out by leading with relevance, clarity, and genuine curiosity. We explore how to create conversations that feel natural, human, and worth responding to. Why Prospects Ignore Most Sales Outreach (00:02:10 – 00:03:35) Ashley explains that buyers aren’t ignoring messages because they’re rude, they’re overwhelmed. Generic outreach, vague value statements, and self-focused messaging give prospects no reason to engage. The real issue isn’t volume, it’s relevance. The Biggest Mistake Salespeople Make in Messaging (00:03:35 – 00:05:10) Most outreach talks about the seller instead of the buyer. Ashley shares why messaging that leads with credentials, features, or company history immediately creates disengagement. Prospects care less about who you are and more about whether you understand them. How to Personalize Without Overcomplicating It (00:05:10 – 00:06:55) Personalization doesn’t mean writing long messages. Ashley explains how small signals like role relevance, timing, and context, dramatically increase response rates without extra effort. Relevance beats creativity every time. Using Curiosity Instead of Pressure (00:06:55 – 00:08:30) Rather than pushing meetings, Ashley encourages sellers to spark curiosity. Open-ended questions invite conversation and reduce resistance, making prospects feel in control instead of sold to. Pressure ends conversations. Curiosity starts them. How to Earn Replies Without Chasing Prospects (00:08:30 – 00:10:05) Ashley breaks down why follow-ups fail when there’s no value added. Each touchpoint should introduce a new insight, observation, or reason to respond not just “checking in.” Silence is feedback. Adjust accordingly. What High-Performing Sellers Do Differently (00:10:05 – 00:12:10) Top performers focus on quality conversations, not activity metrics. Ashley explains how intentional outreach, patience, and consistency lead to better pipeline health and stronger relationships. Selling is about connection, not coercion. Key Lesson: Make It About Them, Not You (00:12:10 – 00:13:55) When outreach is centered on the buyer’s world, challenges, and priorities, responses come naturally. Sales success comes from empathy, relevance, and respect, not persistence alone. “If your message doesn’t immediately answer ‘Why should I care?’, it won’t get a reply.” – Ashley Winston Resources Want help applying these strategies directly to your pipeline and hitting your quota? Join The Sales Evangelist Mastermind, a 90-day program designed to help you close more deals and hit your number. Learn more at thesalesevangelist.com/mastermind Sponsorship Offers This episode is brought to you in part by HubSpot. With HubSpot Sales Hub, your data, tools, and teams come together on one platform to help you close deals faster. Try it at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Tired of prospects not responding? Get a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your LinkedIn outreach and land 3–5 appointments with our LinkedIn Prospecting Course. Visit a href="http://thesalesevangelist.com/linkedin" rel="noopener noreferrer"...

    33 min
  2. How Properly Conduct a Discovery Call & Not Scare Away Your Prospect

    12/22/2025

    How Properly Conduct a Discovery Call & Not Scare Away Your Prospect

    Traditional selling pushes prospects away. In this episode, Jeremy Miner breaks down why old-school persuasion no longer works and how modern buyers respond to questions that help them uncover their own problems and motivations. We explore how to reduce resistance, increase trust, and guide prospects to decisions without pressure by using a question-based, psychology-driven approach. Why Prospects Resist Being Sold (00:02:14 – 00:03:40) Jeremy explains that buyers are more informed than ever and can sense manipulation instantly. When salespeople push solutions too early, prospects naturally defend themselves by shutting down or disengaging. The key problem isn’t price or timing, it’s resistance created by the sales approach. Why Features and Pitches Kill Momentum (00:03:40 – 00:05:22) Most sales conversations fail because sellers talk too much about themselves. Jeremy shares why feature-dumping and early pitching overwhelm buyers and prevent emotional engagement. People don’t buy when they’re told, they buy when they discover. How Question-Based Selling Reduces Pressure (00:05:22 – 00:07:10) Instead of convincing, Jeremy teaches how to guide prospects with thoughtful, problem-aware questions. The goal is to help buyers verbalize: Their challenges The consequences of not changing The urgency to act When prospects say it themselves, belief and commitment increase. Helping Prospects Connect Emotion to Problems (00:07:10 – 00:08:55) Logical reasons start conversations, but emotional reasons close deals. Jeremy explains how to ask questions that uncover frustration, fear, or missed opportunity without sounding manipulative. Emotion creates urgency; logic justifies the decision. How to Talk About Solutions Without Sounding Salesy (00:08:55 – 00:10:30) Jeremy emphasizes delaying solution talk until the prospect fully understands their own problem. When solutions are positioned as answers to their words, not your pitch, resistance disappears. Timing matters more than wording. Preventing Ghosting by Creating Commitment (00:10:30 – 00:12:05) Ghosting happens when prospects aren’t emotionally invested. Jeremy explains how confirming commitment throughout the conversation instead of at the end, keeps deals moving forward. If there’s no internal urgency, follow-ups won’t matter. The Role of Neutrality in Closing More Deals (00:12:05 – 00:13:55) One of the most powerful ideas Jeremy shares is remaining neutral. When sellers stop needing the deal, prospects feel safer opening up and making honest decisions. Confidence comes from control not pressure. Key Lesson: Stop Convincing, Start Guiding (00:13:55 – 00:15:30) The biggest shift modern sellers must make is moving from persuasion to facilitation. When prospects feel understood instead of sold to, decisions happen faster and with less resistance. “The moment you stop trying to convince someone is the moment they start convincing themselves.” Jeremy Miner Resources Learn more about Jeremy Miner and his question-based selling framework at: 7thlevelhq.com Explore training on modern selling psychology and objection-free conversations. Want help applying these strategies directly to your pipeline and hitting your quota? Join The Sales Evangelist Mastermind, a 90-day program designed to help you close more deals and hit your number. Learn more at thesalesevangelist.com/mastermind Sponsorship Offers This episode is brought to you in part by HubSpot. With HubSpot Sales Hub, your data, tools, and teams come together on one platform to help you close deals faster. Try it at hubspot.com/sales. This episode is brought to you

    37 min
  3. You’re Closing Too Late, Here’s How to Fix It!

    12/19/2025

    You’re Closing Too Late, Here’s How to Fix It!

    You have a discovery call with a prospect, and they seem interested in your product—until it's time to follow up. After three attempts, you finally get the message: you waited too long to close the deal. What can you do differently to prevent this from happening again? Listen to my chat with Benjamin Dennehy, who explains why sellers often get stuck in a "matrix" and how it prevents them from closing deals at the right time. Meet Benjamin Dennehy · Meet Benjamin Dennehy, known as the UK’s most hated salesperson, all thanks to his amazing marketing campaign. · He shares how sellers often make the mistake of closing when prospective buyers are expecting them to. · Don’t forget that you’re the one with all the power when it comes to choosing the right time to close a deal. The Sales Matrix: Closing At The Wrong Place · When first starting in the industry, Benjamin discovered that most sellers live in a system they don’t realize they’re part of. This is another reason why sellers tend to close deals at the wrong time. · There are also two systems when sellers are out in the field: the buyer's system and the seller’s system. The problem arises when these two systems intertwine, making the buyer appear as the winner. · Due to conditioning, buyers are aware that if they say no to a seller, the seller won't stop. So, they think of other ways to try to keep sellers from continuing without actually saying no. · Benjamin delves into the list of reasons why prospective buyers give objections or deceive sellers to prevent a deal from moving forward. I'm sure you’ve heard plenty of these! · He also explains how the matrix is designed to prevent sellers from exerting control in closing deals, and how their buying habits lead them to sympathize with prospective buyers when they express their objections. How to Get Out of the Sales Matrix · To get out of the sales matrix, Benjamin shares that sellers must start closing at the beginning of the first meeting. When you try to close at the end, you give the buyer complete control over what happens next. · At the start of the meeting, Benjamin does three things to get a prospect to say no: o Get permission from them to say no. If they believe the product is of no use, then there's no point in continuing the conversation. This will also let you know if the person you're speaking to is the decision-maker. o When speaking with the CEO, he asks a series of questions to determine if he can actually assist their company with their problem. If there's no "no" in these answers, then he moves on to the third step. o This is when he'll discuss how they can move forward together to close a deal. · The method works because if prospects aren't logically saying no, then they have to agree to move forward. “We've been told a lie that the person with all the money has the power. But in reality, money only has power when someone wants it.” - Benjamin Dennehy. Resources Follow Benjamin on LinkedIn, YouTube, and Instagram. Don't forget to DM the code TSE for a link to his two free courses. You can also learn more about him on his website. Sponsorship Offers 1. This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a...

    33 min
  4. Three Reasons Most Enterprise Deals Stall

    12/15/2025

    Three Reasons Most Enterprise Deals Stall

    In this episode of the Sales Evangelist podcast, Donald C. Kelly reveals the top three reasons why enterprise deals stall, offering listeners practical solutions to overcome these hurdles. Whether you're new to enterprise sales or struggling to close deals, this episode is packed with actionable insights that can elevate your sales game. Misalignment Within the Buying Committee ● Understand that decisions in enterprise sales are often made by committees, leading to internal misalignment among stakeholders. ● Use a mutual action plan to align all committee members, ensuring everyone is on the same page and clear about the project's importance. ● Leverage tools like digital sales rooms to facilitate communication and provide access to demos and materials for all committee members. Perceived Risk and its Impact ● High perceived risk can paralyze decision-makers; ensure to highlight previous successes with similar organizations to reduce apprehension. ● Customize demos to reflect the prospect's unique environment, showcasing specific processes to minimize perceived risk and create relevance. Providing Clear Value ● Focus on the most impactful features that resonate with each committee member to highlight your solution’s value effectively. ● Use stories, testimonials, and case studies to reinforce the solution’s benefits and drive home its ROI, ensuring buyers see the potential for personalization and growth. Homework Challenge or Action Steps ● Create a mutual action plan for your next enterprise deal to foster committee alignment. ● Focus on understanding each committee member's individual goals and challenges related to the project. "Don't sell on everything—sell on the thing that matters the most." ● Donald C. Kelly. Timestamps ● 00:00 ● Introduction ● 01:20 ● Misalignment Within the Buying Committee ● 03:44 ● Perceived Risk and its Impact ● 08:32 ● Providing Clear Value ● 10:58 ● Closing thoughts Resources ● Sales Evangelist Mastermind: [Join Here](https://thesalesevangelist.com/mastermind) ● Mutual Action Plan Guide: [Learn More](https://www.mutualactionplan.com) Sponsorship Offers 1. This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. 2. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. 3. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

    11 min
  5. Three Simple Questions To Stop Deals From Slipping

    12/12/2025

    Three Simple Questions To Stop Deals From Slipping

    Deals keep slipping through the pipeline? As Q4 pressure builds, many sales teams find themselves pushing deals forward without fully understanding what is stalling them. Bob Kocis, author of The President’s Club Mindset, joins the episode to share why deals stall and what top performers do differently.  Drawing from decades of experience in sales technology and executive leadership, Bob shares a practical framework built around three questions that help sales reps regain control of their pipeline and close with confidence. Meet Bob Kocis ·  Bob Kocis is the President and Chief Operating Officer of Aptean and the author of The President’s Club Mindset: Inside the Winning Strategies of Tech’s Most Successful Salespeople. ·  His career spans senior leadership roles across the tech industry, including Chief Revenue Officer at Continuum Managed Services, Vice President of Worldwide Sales and Customer Excellence at Ansys Inc., and Senior Division Vice President at PTC. ·  Bob is widely recognized for helping organizations build strong sales cultures where top performers thrive, teams navigate complex go-to-market models, and revenue growth becomes predictable through discipline and execution. The Three Critical Questions to Prevent Slippage ·  Bob introduces a simple but powerful framework centered on three questions every seller and manager should revisit throughout the sales process. o   First, why is the customer buying anything at all? This requires uncovering the true business problem, not just surface-level interest. Agenda-free listening helps reveal the real motivation behind the deal. o   Second, why are they buying from us? Sales reps must clearly articulate their unique value and help the customer envision success. This goes beyond features and focuses on meaningful differentiation. o   Third, why should they buy right now? Without a compelling event, deals drift. Building a mutual action plan creates urgency and gives internal champions a roadmap they can share. Bob Kocis’s Main Advice ·  Stay curious and keep asking better questions. When deals are grounded in these three fundamentals, forecasting improves, confidence grows, and pipeline slippage becomes the exception rather than the rule. “I like this idea of agenda-free listening, right? Where you’re really listening intently and you don’t actually have an agenda, so you’re really hearing what they’re saying.” — Bob Kocis Resources Get Bob’s book: The President’s Club Mindset  Connect with Bob Kocis on LinkedIn Join The Sales Mastermind at thesalesevangelist.com/mastermind. Check out Blue Mango Studios for podcasting production.  Sponsorship Offers 1.  This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. 2.  This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at...

    30 min
  6. Turn LinkedIn Connections Into Sales Conversations (Even If You're Scared)

    12/08/2025

    Turn LinkedIn Connections Into Sales Conversations (Even If You're Scared)

    It’s getting close to the end of the year, and every connection feels like it needs to turn into a deal. But how can you close a deal when prospects keep ghosting you, especially when money enters the conversation? Here are five tips to help prevent prospects from ghosting after you send a proposal. The Real Reasons Prospects Disappear ·  Here are two root causes of why ghosting usually happens: o  The prospect isn’t truly committed to solving their problem. o  The pricing isn’t aligned with their expectations. ·  Try to differentiate between prospects who are simply gathering information and those who are genuinely committed to taking action. This helps address the root causes of ghosting. Discuss and Establish the Budget Upfront ·  Never skip the money conversation. Sales is ultimately an exchange of money for value, so start the discussion openly and early.  ·  Provide a price range rather than simply asking if they have a budget. This helps anchor the conversation and makes the topic less awkward. Understand the Buyer’s Decision-Making Process ·  Ask how decisions are made, when they happen, and who is involved. Go beyond generic questions like, “Are you the decision maker?” Instead, ask about their process: o  Are they evaluating price only, or are features and other factors involved? o  Do they use a scoring system or other internal criteria? o  Who else will be part of the decision ·  Probing these areas helps you avoid surprises and ensures you stay involved throughout the process. Use a Mutual Action Plan ·  Create a mutual action plan that outlines tasks, milestones, deadlines, and responsibilities for both sides.  ·  This doesn’t require fancy software. A simple spreadsheet works just fine. Having a shared plan reduces ghosting by making next steps clear and mutually agreed upon. Set a Proposal Review ·  Instead of emailing a proposal and hoping for the best, schedule a meeting to review it together.  ·  Even a ten-minute call can make a difference. This allows you to explain details, clarify pricing, address questions, and confirm alignment before moving forward. “Sales is where you’re exchanging money for a product or a service. Why would that be awkward when that is the most important part of the whole process?” — Donald Kelly Resources Join my Sales Mastermind to get real-world feedback, accountability, and proven strategies from fellow sellers and myself. If you need help creating content for your business, my podcast production agency, Blue Mango Studios, can help.  Sponsorship Offers 1.  This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. 2.  This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at a href="https://business.linkedin.com/sales-solutions/cx/20/09/sales-navigator-podcast?src=re-pod&trk=tse&veh=tse&mcid=6897323946090332160" rel="noopener noreferrer"...

    19 min
  7. Stop Avoiding Price Conversations: Say This Instead

    12/05/2025

    Stop Avoiding Price Conversations: Say This Instead

    Talking about price doesn’t have to feel awkward or cost you deals. In this episode, I break down how to bring up pricing early and confidently without sounding pushy or salesy. Building on insights from a previous episode on ghosting, I explain why delaying the price conversation creates friction, buyer anxiety, and stalled deals, and how transparency actually builds trust. Why Salespeople Avoid Talking About Price (00:02:28 – 00:03:32) Most salespeople delay price because it feels uncomfortable. They wait for the buyer to bring it up or hold it until the very end, hoping everything works out. The problem is simple: buyers don’t like surprises. When pricing isn’t clear, anxiety grows and momentum slows. The Risk of “Showing Value First” (00:03:32 – 00:05:12) Many sellers believe they need to prove value before talking about cost. But if a buyer can’t afford the solution, no amount of value will make the deal work. Selling a $10,000 solution to someone looking for a $1,000 fix creates unnecessary friction and wasted time. When to Introduce Pricing in the Sales Process (00:05:12 – 00:06:58) Pricing should come up during discovery after you understand the problem, impact, and urgency. Early alignment helps both sides decide quickly whether it makes sense to continue the conversation. How to Share a Price Range Without Sounding Salesy (00:06:58 – 00:08:18) Instead of hiding the number, be transparent and give a realistic range: “Based on what you’re sharing, clients who partner with us typically invest between $16,000 and $19,000. Is that within the range you’ve discussed internally?” This keeps the conversation collaborative instead of transactional. What to Do If the Price Is Too High (00:08:18 – 00:10:04) If a prospect says the price is too high, don’t rush to discount. Acknowledge it, stay transparent, and ask: “What number have you all discussed internally?” You’ve shared your number, now invite them to share theirs. Tie Price to Outcomes, Not Features (00:10:04 – 00:11:17) Price makes sense when it’s tied to results. Focus on outcomes like revenue impact, conversions, or efficiency gains rather than features. When buyers see ROI, the investment feels justified. Locking in Alignment With a Mutual Action Plan (00:11:17 – 00:13:38) Once budget and outcomes are aligned, confirm next steps: Proposal review dateDecision timelineOnboarding plan A mutual action plan removes ambiguity and reduces ghosting. Resources Want help applying these strategies directly to your pipeline and hitting your quota? Join The Sales Evangelist Mastermind, a 90-day program designed to help you close more deals and hit your number. Learn more at thesalesevangelist.com/mastermind Sponsorship Offers This episode is brought to you in part by HubSpot. With HubSpot Sales Hub, your data, tools, and teams come together on one platform to help you close deals faster. Try it at hubspot.com/sales. This episode is brought to you in part by LinkedIn. Tired of prospects not responding? Get a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. This episode is brought to you in part by the TSE Sales Foundation. Improve your LinkedIn outreach and land 3–5 appointments with our LinkedIn Prospecting Course. Visit a...

    16 min
  8. Why Prospects Ghost After Your Quote (And How to Stop It with Price Commitments

    12/01/2025

    Why Prospects Ghost After Your Quote (And How to Stop It with Price Commitments

    We all know the feeling. You think an inbound deal is good to go, and out of nowhere a competitor pops up and takes it. In this episode, I walk you through why this happens more often than you think and what you can do to stay ahead when prospects quietly start shopping around. Facing the Reality of Multiple Vendors (00:02:29 – 00:05:26) ●    Most buyers are not talking to only one company. In fact, almost every inbound lead is comparing several vendors before they make a decision. ●    I break down the numbers and talk about why you should always assume you are one of many. Even when the lead comes from a referral, there is usually another option on the table. Overcoming the Wait and Hope Pitfall (00:05:26 – 00:09:11) ●    Too many sellers wait and hope the deal closes. That approach usually backfires. In this part of the conversation, I share the exact language you can use to bring up competitors in a confident and natural way. ●    You will also hear how to set a follow up call for a true apples to apples comparison once the buyer has done their research. This helps you stay in control and positions you as a real guide in the process. Stats That Influence Your Strategy (00:07:24 – 00:08:46) ●    92% of buyers already have at least one vendor in mind before they ever talk to you. Most stick with that initial list. ●    I explain how this shapes your outreach, your social presence, and the way you show up early in the buying journey. Scripts and Tactics to Win (00:09:11 – 00:16:27) ●    Here is where we get practical. I share simple scripts to help you confidently ask which vendors they are comparing, how they are evaluating pricing, and what steps they want to take next. ●    I also walk through how confidence, professionalism, and a quick thank you follow up can help you stand out and keep the deal alive. “92% of buyers start the process with at least one vendor in mind, and 90% of them end up choosing from their initial consideration list.” - Donald Kelly. Resources ●    Don’t forget to connect with me on LinkedIn. ●    Check out my LinkedIn Prospecting Course to change your level of thinking and master LinkedIn outreach. ●    If you need help creating content for your business, Blue Mango Studios can help. Sponsorship Offers 1.   This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales. 2.   This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse. 3.   This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three...

    17 min
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About

I believe in doing BIG THINGS! You should be earning 6 figures easily as a sales rep. But chances are you are not...yet! Sales is the most important department in every company but many sellers are never taught how to effectively sell, much less how to earn their way to high-income status. My own career limped along until a company I worked for invested in sales training to help me succeed. Immediately afterward, I closed a deal worth 4X what the company spent on me and saw hockey-stick improvement in my performance. So I started a podcast to “Evangelize” what was working. Today I interview the world's best sales experts, successful sellers, sales leaders and entrepreneurs who share their strategies to succeed in sales right now: folks like Jeffrey Gitomer, Jill Konrath, Bob Burg, and Guy Kawasaki to name a few. They share actionable insights and stories that will encourage, challenge, and motivate you to hustle your way to top income status. If you’re someone looking to take off in your sales career and earn the income you deserve, hit subscribe and let’s start doing BIG THINGS!

Information

  • Creator
    Donald C. Kelly
  • Years Active
    2013 - 2025
  • Episodes
    2K
  • Rating
    Clean
  • Copyright
    Copyright 2025 © The Sales Evangelist Podcast
  • Show Website
    The Sales Evangelist

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