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The Sales Evangelist

The Sales Evangelist

Di: Donald C. Kelly
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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!Copyright 2025 © The Sales Evangelist Podcast Economia Gestione e leadership Leadership Marketing Marketing e vendite Ricerca del lavoro Successo personale
Episodi
  • How to Know if Your Deal is Going South Sooner than Later | Andee Harris - 2036

    How to Know if Your Deal is Going South Sooner than Later | Andee Harris - 2036
    Sep 11 2026
    Sometimes the best way to close more deals isn't by adding new people to your pipeline (though that's always a good thing.) Instead, the best thing is to address the issues that make a deal fail before they fail.In today's episode of The Sales Evangelist, I joined the CEO of Challenger, Andee Harris, to get her take on failed deals and how to address those issues directly with our prospects.Challenger is a sales training company:The Challenger Sale by Matthew Dixon and Brent Adamson explains many of the principles Challenger uses in their training.Early sellers might be timid, which usually leads to a failure to recognize when a deal isn't moving in the right direction.In Andee's experience, continuous feedback is a great way to course-correct throughout the sales process to tailor the experience and selling strategy to the specific prospect.Passive selling isn't the best form of selling for either party. Taking control of the purchase and helping the buyer buy the product is your job.Three ways to notify deals before they go south:Integrate an avenue for continuous feedback. If a buyer likes you as a sales rep, they'll want to share methods to improve their experience.Realize that one size doesn't fit all. What works for one client might not work for another.Constantly be learning. Be curious, and look to understand and be self-aware of your strengths and weaknesses.Andee's final takeaway? Understand that we're in a complex selling environment. Multiple factors influence the selling process, but it isn't impossible to create wins and do phenomenally well. To get in touch with Andee, visit challengerinc.com or connect with Andee on LinkedIn.Sponsorship OffersThis 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.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.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.CreditsAs 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.
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    29 min
  • Your Connection Rate Dropped 80% and Nobody's Talking About It | David Zeff - 2037

    Your Connection Rate Dropped 80% and Nobody's Talking About It | David Zeff - 2037
    Sep 14 2026
    Connection rates have dropped roughly five times since before COVID.If ten percent of your calls used to turn into a conversation, you're probably closer to two now.David Zeff, CEO of Whistle, runs an agency that makes cold outreach work for 350-plus B2B clients, and he broke down exactly what's changed, what hasn't, and the parts of outbound most people are too embarrassed to actually do.Why Connection Rates Have Collapsed Since COVIDDavid's headline stat: connection rates have dropped roughly five times since the early 2010s. If a rep used to get a conversation on ten percent of calls, that number is closer to two percent now.That drops compounds. Fewer conversations means fewer meetings booked from the same amount of effort, cutting a rep's effective output roughly in half even before factoring anything else in.He points out that most investors and boards setting revenue benchmarks don't actually understand how much this single number has shifted, which means the targets built on top of it are often unrealistic from the start.The Four Things Whistle Screens For Before Taking a ClientWhistle turns away clients the way a lawyer might turn down a case they can't win. David treats a signed client as the start of the real work, not the finish line.First: does the founder actually know their ICP? If they're still deciding between multiple very different buyer types, that's a major warning sign.Second: is the total addressable market big enough to support a real sales motion, since a market of a few hundred accounts with multi-year sales cycles isn't a fit for most outbound efforts.Third and fourth: is there real marketing support behind the sales effort, and does the product have any real moat, since neither one used to be a dealbreaker a decade ago the way they are now.The New Risk: Can Your Prospect Just Build It Themselves?David's newest red flag: prospects increasingly ask themselves whether they could just build a simple version of the product using AI tools instead of buying it.His own team has looked at some clients' products recently and had the same reaction: this looks like something built quickly with AI, which means the prospect is likely to think the same thing.Sellers need a clear, early answer to that question, since it's showing up at the very top of the funnel now, not just at the negotiation stage.Why Cold Email Copy Isn't the Real StoryProspects often ask David to see a sample of Whistle's email copy, expecting the wording itself to explain the results.His answer is always the same: seeing the email is like seeing the cheese and asking how that made the pizza. The copy alone leaves out everything that actually got the message opened and read in the first place.Highly personalized details, like referencing someone's favorite sports team, used to work well on their own. David is direct that this stopped being enough years ago, even though it still gets attention on LinkedIn as a screenshot-worthy tactic.Stop Separating the Brand From the PeopleDavid points to Gong as the company that got this right early: during the shift to remote work, they made individual employees visible instead of hiding behind the company logo, including putting reps on billboards.B2C brands have leaned on individual personalities for a long time. B2B is only catching up to that now, and companies that keep everything behind a logo are giving up a real advantage.Donald shared a reference point from a past guest at Chili Piper, who said roughly half the deals in their pipeline had some connection to her personal LinkedIn activity, not because she was directly involved in every deal, but because buyers had engaged with her content somewhere along the way.Build Community Before You Need ItDavid's third layer, beyond the basics and personal branding: building some form of community or network around your business, even a small one.A simple example from one of his own clients: a marketing VP asked if Whistle could bring their clients together to trade notes, which turned into a referral network of consultants and adjacent service providers.It doesn't have to be a massive branded community. Even something as basic as a small referral relationship, a shared cause you donate to together, or a network of people adjacent to your buyer who can talk about your space, counts and compounds over time.The Free Tactic Nobody Will Actually DoDavid's final, deceptively simple tip: export your personal contacts from WhatsApp or your phone, write one honest message explaining what you do and asking for a referral, and send it to twenty people a day.His prediction is that most people won't actually do this, precisely because it's free, easy, and has no clever trick to hide behind if it doesn't work.He's currently running an open deal that came directly from this exact method, reaching out to a personal contact who referred him to someone else who's now moving through the sales process."We're in sales. You're always desperate. That's the...
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    36 min
  • AI Didn't Kill Sales Strategy. It Exposed Who Never Had One | John Stopper - 2038

    AI Didn't Kill Sales Strategy. It Exposed Who Never Had One | John Stopper - 2038
    Sep 18 2026
    AI is changing sales fast. But is it actually replacing salespeople, or is it exposing the sellers who never developed real strategy skills? That’s the question I explore in this conversation with John Stopper.John and I get into the difference between sales tactics and sales strategy, why AI can sometimes give sellers the wrong picture of a buyer, and why getting closer to the people involved in a deal can make the difference between winning and losing. We also talk about how sales teams can use AI to identify deal risks instead of simply using it to write more emails.Why AI Makes Sales Strategy More ImportantAI can teach people sales tactics, but strategy requires a deeper understanding of the situation.Tactics focus on how to sell, while strategy focuses on who, what, when, where, and why.AI can help sellers execute many tactical tasks, but sellers still need to decide which approach fits the buyer and the situation.Strong sales strategy starts with understanding customers and what will actually compel them to buy.The goal is to choose the right strategy based on the conditions of the deal.Tactics vs. Strategy: The Baseball Analogy — 03:38Knowing how to throw every pitch does not mean you know which pitch to throw.A baseball pitcher may have four or five pitches available.The right pitch depends on the batter, pitch count, runners on base, and inning.Sales works the same way. The skill is not just knowing the sales playbook but knowing which strategy to use in the moment.Choosing the right strategy can improve your position, accelerate velocity, and compress time.The Principle of Reality: Don't Trust Every AI Answer AI can give both buyers and sellers information that does not accurately reflect the current situation.Buyers can use AI to research a salesperson or company before the first conversation.Sellers can also build their account research around outdated or incomplete information.A polished AI summary can create false confidence if it does not reflect what is actually happening.Sellers should verify their assumptions instead of treating AI research as unquestionable fact.How to Surface Reality With Better Questions The first sales conversation is an opportunity to check whether both sides are working from the right information.Ask the buyer what their AI research has shown them about your company, product, or you.Share what your research has shown you about their company and ask whether you have it right.Use the conversation to identify what is missing from your research.Verify the situation before choosing your sales strategy.Different Buyers Require Different StrategiesThe right message depends on the person you are selling to.End users often care about doing their jobs faster, better, or cheaper.Managers may care more about how a solution affects their team and the risks involved.Executives are more likely to focus on strategic growth and business outcomes.Sellers need to understand the buyer's role before deciding what value to emphasize.The Principle of Proximity: Get Closer to the Buyer “Proximity sells” because sellers need to understand the buyer's world deeply enough to bring useful insight.Proximity is not about becoming the buyer's friend.It means understanding the buyer's business and seeing things from both inside and outside perspectives.Sellers should get close to the people who can influence the deal, not only the person who can approve it.Outside experience can help sellers bring insights the buyer may not have considered.Find the People Who Can Say No A deal can have strong champions and still fail because someone else inside the organization has the power to stop it.Identify the people who may resist the purchase.Ask your champion who in the organization could have concerns about the solution.Reach out to those people directly instead of waiting for their objections to appear later.Address potential resistance before it becomes a deal-ending problem.Use AI to Identify Deal Risk AI can be useful when it helps sellers think through what could go wrong.Ask AI to research the people and roles that may resist a purchase.Identify possible objections and resistance points before they appear.Continue updating the research as the deal progresses because new risks can emerge.Use AI to help build a deal strategy around what could prevent the deal from closing.Bridging Strategy: Build Relationships Across the Account One salesperson should not have to carry every relationship in a complex B2B deal.Sales managers can connect with the buyer's manager.Product leaders can connect with the buyer's technical leaders.CEOs can connect with other executives when the situation calls for it.Each person can carry a message that matches their role and expertise.Multiple relationships can help both companies become more familiar with each other.Why Executives Still Have a Role in Selling Executive involvement can be part of the sales process, especially when selling complex ...
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    34 min
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