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The Sales Evangelist

Donald C. Kelly

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!

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  • #2048
    Friday · 14 min

    4 Ways I’m Using AI in My Sales Process Right Now | Donald C. Kelly - 2048

    A year ago, I thought AI was mostly a research tool. That assumption didn't age well. In this solo episode, I walk through the four places AI actually earns a spot in my sales process today and where I still insist on doing the work myself. Finding the Right Prospects Without Guessing I use a tool called Zenith to research prospects on LinkedIn through Sales Navigator, pull up what they've recently posted, and queue up a relevant comment or connection request based on that content. A human still has to approve every message before it goes out. I'm not letting this run unsupervised, and I edit plenty of what it drafts before it reaches anyone. This process alone books around three appointments a week for me, and the difference comes from how relevant the outreach is, not just how much of it there is. Building Sharper Prospect Lists With AI Research I connect Claude to data platforms like Apollo and Lusha to build and enrich prospect lists for email campaigns with a level of precision that used to take hours of manual digging. A real example is finding publishers in a specific state who have a set number of books releasing this year and a newly hired director over content. That's the kind of narrow, specific research AI handles well. AI can find better prospects, but it isn't sending the emails or doing the relationship work on its own. The research has to be precise and relevant, and that precision is what actually moves the needle. Meeting Recaps, Follow-Ups, and Prep Emails Fathom joins my calls and takes the notes, then Claude turns those notes into a meeting recap with clear next steps that I can send straight to the prospect. That same process updates our in-house CRM automatically, logging notes and creating follow-up tasks on the account without me touching a keyboard. Before the next call, I can also get a prep email drafted that references the last meeting's action items and asks the prospect to confirm or add to the agenda, which saves a meaningful chunk of prep time. Drafting Proposals From Discovery Call Notes I can take the notes and conversation from a discovery call and have our AI agent draft a full proposal based on what was actually discussed, following our standard template. AI drafts it, then my team or I review and refine it before anything goes out, since it isn't perfect every time and can misstate an address or an offering if the original prompt wasn't clear enough. Human judgment is still required on scope and pricing specifically. AI has helped me think through pricing structures for different types of clients, but I'm the one making the final call. Keeping the CRM Honest AI logs my activity and updates CRM records and pipeline stages automatically, which keeps the data current without me manually entering it after every call. The accuracy still has to be mine to own. Whatever the pipeline shows is what I'm reporting up to leadership, so I double-check that it reflects reality rather than trusting the automation blindly. Dictation tools like Wispr Flow are pushing this even further, letting reps update records and direct their AI agents by talking instead of typing, which is only going to get more common. What AI Still Doesn't Replace AI doesn't replace the relationship, the judgment calls, or the actual conversation with a prospect, and that's exactly where I want to be spending more of my time. Research has shown reps spend a large share of their time, somewhere around 60%, on administrative work instead of actual selling, and that's the gap AI is closing for me. Some teams are taking this even further with inbound lead bots that hold full conversations and book meetings directly onto a calendar, with zero human touch until the call itself. "AI handles the admin so that I can spend more time actually selling." — Donald C. Kelly Leadership Advice, Books, and Quotes My challenge for you is: Write out or dictate your entire sales process to Claude or ChatGPT and ask it to identify exactly where AI or an agent could take something off your plate. Most reps underestimate what's possible here, mainly because it feels unfamiliar, not because the tools can't handle it. Resources Tell me what AI tools you're using, or why you're holding off, on LinkedIn. Check out Zenith for LinkedIn-based prospecting and outreach. Check out Fathom for automated meeting notes and recaps. Check out Wispr Flow for voice dictation that updates your tools directly. Check out Apollo and Lusha for prospect data and list enrichment. Sponsorship Offers 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. 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. 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.

  • #2047
    October 19 · 32 min

    Managing AI Agents Is Just Like Managing A New Employee | Kristie Jones - 2047

    Kristie Jones treats her AI agent like a four year old. Not as an insult, as a management strategy. The same way she taught her son "no touch" before he understood why, she's learned that agents need boundaries, check-ins, and correction, just like any new hire. Kristie, founder of Sales Acceleration Group and author of the upcoming book The Sales Leadership Gap: Leading Humans in an AI Augmented World, walked me through what it actually looks like to lead a sales team that's now part human, part automation, and part AI agent. Why Most Sales Teams Are Only Talking About AI, Not Using It Kristie's blunt read on the market: sales leaders are talking a good game on AI adoption, but very few are actually walking it. She calls the hesitation "freeze mode," people waiting for the technology to settle down before they commit to anything. Her pushback: the pace of AI isn't going to slow down, so waiting for the dust to settle just means a competitor gets the head start instead. From Pilot to Control Tower: Managing a Hybrid Team Kristie's analogy for what's changed: sales leaders used to be the pilot, flying the plane directly. Now the job is running the control tower. A modern sales team isn't just a group of humans anymore. It's humans, automation, and AI agents all working together, and leading that requires a 360-degree view no single seat inside the plane can give you. She hasn't seen a single sales leadership course that actually teaches this. Most leaders are being asked to figure it out on their own, in real time, while still being expected to hit quota. Treat Your Agent Like a New Employee (or a Four-Year-Old) Kristie's favorite framing, borrowed from someone else: manage your agent the way you'd manage a toddler, with simple, repeated boundaries, like teaching a child "no touch," some for safety and some just to prevent a mess. Building an agent isn't a "set it and forget it" project. Just like a new hire, it needs a handbook, but it also needs regular check-ins, since no handbook covers every exception. If your business is changing, and it always is, an agent that never gets revisited will quietly drift out of step with how your team actually works. Trust But Verify Kristie built an agent that reviews her AI notetaker every Friday at 4pm and delivers her to-do list by day. The first Friday it was supposed to run, it didn't. Her response mirrored exactly how she'd handle a new employee's mistake: no anger, just a direct conversation about what happened and how to prevent it next time. Her rule going forward: trust the agent to do the work, but verify the output regularly, the same discipline she'd apply to any new hire still earning full independence. Where to Start: Update Your Playbook Before You Automate It Kristie pushes back hard on the idea that sales playbooks are dead. They're not, but most of them are badly out of date, built once and handed to new hires without ever being revisited. Her recommended first step for any leader building agents: go back to the actual playbook, confirm it reflects how work really gets done today, then look at it again through a new lens, asking which of these tasks could be automated. Skipping this step means building automation around a process that's already wrong, which just makes the wrong process faster. Two Agents Kristie Actually Built Her first agent connects Claude Cowork to HubSpot, Granola (her AI notetaker), and Google. Every Friday at 4pm, it reviews her week's meetings and delivers a day-by-day to-do list of everything she committed to. Her second is a research agent, built to be extensive enough that she now teaches a class on building one at Sales Gravy University. Neither required a dedicated engineering team. She built both herself as a sales leader, which is exactly the point: if your company doesn't have a go-to-market engineer or enablement team, this becomes your job by default. Write a "Role Brief" for Every Agent Kristie's upcoming book outlines five leadership competencies and five AI competencies leaders will need, and one of the practical tools she recommends is what she calls a role brief. A role brief is a formal, written document for an agent, similar to a job description but for AI: what decisions it's allowed to make, what decisions always stay human, what the output should look like, and who owns checking it. Every agent a team builds should have one of these, the same way every human hire gets a real job description instead of a vague verbal understanding of the role. The Two Things That Make AI Dangerous If Left Unchecked First, AI is built to solve problems, which means if it can't find a real one, it may manufacture one to justify itself. Second, AI essentially never says it doesn't know, and it almost never asks for a leader's opinion. It delivers a confident answer even when the underlying accuracy is shaky. Both are reasons an agent can never be treated as fully autonomous. Someone still has to be checking the actual output, not just assuming the system is right because it sounds certain. We've Been Here Before: What the World Wide Web Panic Teaches Us Kristie points to the early internet as the closest historical parallel: people worried about losing control over where their information came from, the same fear now aimed at AI. Entire households once relied on a single printed encyclopedia set as the trusted source of information. That system eventually gave way, the same way old assumptions about static CRMs and manual workflows are giving way now. Her takeaway isn't to ignore the risk, but to recognize that fear of a major shift isn't new, and the companies that adapt early are the ones that come out ahead of it. What AI Fluency Actually Means Kristie is now asking about AI fluency directly in client hiring processes, and she defines it as a systems-level understanding of AI, not just knowing how to use one tool. That includes prompt literacy (can someone actually write a prompt that gets a useful result), output evaluation (how do you know if the agent's work is accurate or has quietly drifted), and tool selection (which AI platforms actually get adopted, standardized, and connected across the team). She's blunt with companies that call themselves "AI forward" but don't teach any of this during onboarding. Claiming the identity without building the actual skill doesn't hold up. Your First Step to Becoming AI Fluent Kristie's advice for any seller or leader who hasn't started: pick one tool, whether that's ChatGPT or Claude, and go build something small, like a custom GPT or a simple project. If you don't already use an AI notetaker, that's the bare minimum starting point, and she recommends having one in place within the week. Her closing advice is permission to fail: go make a mistake. Her own Friday agent didn't run the first time she built it, and that's a normal, expected part of learning the tool, not a sign it isn't worth doing. "I treat my agent like a four year old." — Kristie Jones Resources Connect with Kristie Jones on LinkedIn. Visit Kristie's site, Sales Acceleration Group. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. 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.

  • #2046
    October 16 · 17 min

    Predicting the Hang Up: How Sales Fear Fulfills Itself | Donald C. Kelly - 2046

    The phone rings, they pick up, and before you've said a single word, you've already decided how this call is going to go. In this solo episode, I break down a pattern I see constantly in sales reps, including myself in the past. We walk into calls expecting rejection, and that expectation changes our behavior enough to actually cause it. The Prospect Isn't Reacting to Your Offer; They're Reacting to You Sociologist Robert K. Merton gave this phenomenon a name, "the self-fulfilling prophecy," a false belief that causes the exact behavior that makes the belief come true. Your expectation shapes how you act, and the other person responds to how you act, not to your actual intention or your offer. When a rep assumes a prospect is annoyed or uninterested based on nothing more than a hunch, that assumption changes their tone, their pace, and their confidence, and the prospect picks up on all of it. Where This Shows Up Most in a Sales Call Pricing is a major one. A rep starts offering a discount before the buyer has said a word about cost, which quietly signals the product isn't worth the full price in the first place. Email openers are another. Starting with "sorry to bother you" or "I know you're busy" trains the prospect to treat you like an interruption instead of someone trying to solve a real problem for them. Discovery calls suffer the same way. Reps skip the deeper questions because they assume the buyer won't want to answer them, and those deeper questions are usually exactly where the real insight lives. Follow-Up and Demos Take the Hit Too Some reps don't even book the follow-up call because they've already decided the prospect is going to ghost them, which kills the deal before it ever had a real chance. During demos, the same fear shows up as rushing through slides because a rep assumes the buyer is bored, when in most cases that assumption is just wrong. I had this happen recently on a client call. I assumed the prospects weren't engaged, but they were actually just muting themselves out of courtesy while discussing something privately on their end. Why We Do This to Ourselves Predicting rejection in advance is a defense mechanism. It hurts less when the rejection actually happens because some part of you already expected it. A bad call or two can quietly overgeneralize onto every prospect after it, even when the next person has nothing to do with what happened before. A lack of preparation makes this worse. Showing up to a call without enough research or practice leaves a rep feeling shaky, and that shakiness gets mistaken for a sign the call is doomed. How to Break the Pattern Separate the data from the story. Ask yourself what the prospect has actually said or done so far, and if the honest answer is "nothing yet," you're reacting to a story you made up, not to reality. If a prospect sounds off on the call, don't assume the worst. You can simply ask whether now is a bad time and offer a short version of your pitch instead, which hands control of the conversation back to you. Slow down on purpose. A calm opener earns far more attention than a rushed one, because rushing signals inexperience, while a steady pace signals quiet confidence. Prepare Like the Outcome Depends on It, Because It Does Know your opener and your first two questions so well that nerves never get the chance to take over, and practice them out loud until they feel automatic. Walk into every call expecting the best-case scenario instead of the worst, treating each prospect like they could become your best client, because that energy is genuinely palpable through the phone. Your prospect will often meet you at your own level of confidence, so the energy you bring into the call tends to come right back at you. The Five-Call Challenge On your next five calls, write down the negative outcome you're expecting before you dial, then write down what actually happens afterward. Most reps who try this find the gap between what they feared and what actually happened is much bigger than they expected. Once you can see that gap clearly, it gets a lot harder to keep walking into calls assuming the worst. "Stop writing the rejection, and start writing the progress." — Donald C. Kelly Resources Have a story about catching yourself in this pattern? Send me a message on LinkedIn and let me know how it worked out. Want coaching on building a repeatable opener and call process? Check out our Sales Mastermind. Sponsorship Offers 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. 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. 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.

  • #2045
    October 12 · 39 min

    4 Steps to Systematic Sales Growth | Jimmy Burgess - 2045

    "Broke, rich." That's the two-word test Jimmy Burgess uses to explain whether a sales career is working: phone up to your ear, you're rich; phone down, you're broke. Pulled from our archive, Jimmy, Chief Growth Officer at Berkshire Hathaway HomeServices Beach Properties of Florida, is with me as we discuss the four-step pattern he lays out for turning scattered activity into steady, repeatable growth that hasn't aged a day. Growth Follows a Pattern, and It Starts With Confidence Systematic growth runs through four connected stages: competence builds confidence, confidence leads to consistent repetition, repetition builds a reputation that earns more opportunities, and those opportunities turn into conversations that convert. Skipping any one of those stages, or doing them inconsistently, is why so many reps feel like they're working hard without seeing the compounding results they're after. The whole cycle starts with the individual seller, not the market or the lead source, because confidence is what makes every later stage possible. Step One: Always Be Learning, Not Always Be Closing The old "always be closing" mindset gets replaced with "always be learning," meaning the real advantage comes from becoming the most knowledgeable person in your field, not the most aggressive closer. Confidence works like walking into a dark room versus a lit one: uncertainty about your product or market makes you move cautiously, while real expertise lets you walk in boldly and handle whatever comes up. There's no excuse for staying stuck on a weak spot right now, since free training on virtually any topic is one search away, and the only real barrier is the discipline to keep learning instead of getting comfortable. Step Two: Repetition Builds Reputation Consistent, visible value, like a weekly video update or a regular check-in, is what builds a buyer's trust before they've ever had a real conversation with you. One real story drove this home: a stranger at a local event recognized a familiar face from a weekly video list, introduced himself, and said, "I'm on your mailing list, you're my guy," despite never once responding to an email. The accountability piece matters just as much as the consistency itself; running small weekly groups where people report their leading indicators, like a set number of conversations, keeps that repetition from quietly slipping. Step Three: Conversations Lead to Conversions Social posts and videos warm people up, but real trust and real deals still come from an actual conversation, which means picking up the phone remains non-negotiable. A blunt phrase sums it up well: hold an imaginary phone up to your ear and the choice is simple, "phone, rich" or "no phone, broke," because business still happens through direct conversation, not passive content. Confidence built through learning is what makes those calls easier, since a well-prepared rep isn't scrambling for answers mid-call, they're simply having the conversation they already know how to have. Step Four: Raving Fans Become Your Referral Engine Most reps put all their effort into winning the deal and then go quiet right after the transaction closes, which is exactly the moment real referral opportunity gets left on the table. Turning a client into a referral source means doing something genuinely unexpected tied to what matters to them personally, like giving a family's kids a small surprise gift at closing instead of another generic thank-you. A simple follow-up call weeks after the transaction, just checking that everything's still going well, keeps you top of mind and is what actually generates referrals, since referrals come from what happens after the sale, not during it. Growth and Comfort Cannot Coexist A personal story about a 13-year-old finishing third in his first cross-country meet became the closing message: real growth only happens when you choose to run into discomfort instead of away from it. The advice for reps avoiding the phone, avoiding a hard skill, or avoiding an uncomfortable conversation is the same: anyone can push through roughly seven minutes of discomfort, and what's on the other side is usually exactly what they wanted. Staying comfortable isn't neutral, it's actively dangerous for growth, since decline tends to follow closely behind any extended stretch of comfort in a sales career. "Growth and comfort cannot coexist." — Jimmy Burgess Resources Connect with Jimmy Burgess on LinkedIn. Check out The Real Estate Sales Podcast, where industry experts share strategies that apply well beyond real estate. Sponsorship Offers 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. 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.

  • #2044
    October 9 · 33 min

    The Top Three Issues Killing Your Sales Deals | George Bronten - 2044

    You did everything right, or at least you thought you did, and the deal still fell apart anyway. This one is coming from the archives, and the principles hold up just as well today as they did when we first recorded it. George Brontén, founder and CEO of Membrain and author of Stop Killing Deals, broke down the three deadly assumptions that quietly sink B2B sales deals, and how to catch them before they cost you the close. The Three Assumptions That Quietly Kill Deals Deals rarely fall apart because of one dramatic mistake, they fall apart because of small, invisible assumptions that go unchecked from the first call all the way to the close. The first flawed assumption is believing salespeople are simply born with the right traits, which leads to hiring extroverted, competitive people regardless of whether those traits actually fit the sales environment being sold into. A transactional sale and a complex, multi-year B2B sale call for completely different skill sets, so hiring for one generic "salesy" personality type instead of the specific environment is a mistake that shows up later in lost deals. Why Buyers Don't Decide Rationally The second assumption is believing buyers will act rationally once they're shown a logical case for the product, when in reality people buy with emotion first and rationalize the decision with logic afterward. Proving a product is the better choice on paper doesn't guarantee a rational decision back, because the buyer's hesitation is usually tied to internal risk, politics, or past experience that logic alone can't resolve. Understanding that gap between what buyers say and how they actually decide changes how a rep should run a sales conversation, shifting it from a pitch toward a genuine discussion about what's really driving the decision. The Myth of the Naturally Disciplined Seller The third assumption is expecting salespeople to be naturally disciplined enough to do whatever it takes to hit a number, when discipline is actually a set of habits that has to be built deliberately, not a trait people are simply born with. A lack of discipline shows up in small, specific gaps, like failing to identify every stakeholder in a deal or skipping a promised follow-up, and those small gaps are what let a deal quietly stall. The fix isn't willpower, it's building daily habits and structure into the sales process itself, so discipline becomes the default instead of something a rep has to summon on a hard day. The Number One Deal Killer: Not Knowing How the Decision Gets Made The single biggest issue killing B2B deals is not understanding how the buying decision will actually be made, or who besides the friendly first contact needs to be involved before anything moves forward. A rep can have a great conversation with an enthusiastic champion and still lose the deal entirely, because that champion was never the one with the authority or budget to make the final call. The fix is asking directly, early in the first call, how this kind of decision typically gets made and who else needs to weigh in, instead of assuming the friendly voice on the phone speaks for the whole organization. Why Discipline Determines Whether Deals Survive A lack of discipline often shows up as avoidance, like a rep who knows there are more stakeholders to loop in but skips that step because the conversation feels uncomfortable. One real example was a sales team that avoided engaging technical stakeholders because those conversations felt intimidating, so those technical buyers later torpedoed the deal out of fear the product would automate away their jobs. Once that sales team was coached to have those uncomfortable technical conversations directly, framing the product as freeing people up for better work instead of threatening their jobs, their win rates tripled. "If you can always identify all the right stakeholders in every deal, and if you have a sales team and you just focus on that for one year, you're going to improve your results massively." — George Brontén Leadership Advice, Books, and Quotes George Brontén is the author of Stop Killing Deals: How to Avoid Deadly Assumptions and Achieve Sales Excellence, which breaks down the three assumptions covered in this episode in more depth, along with practical ways to diagnose which one is hurting your own pipeline. Resources Connect with Brontén on LinkedIn. Learn more about Membrain, the sales enablement CRM built to guide, coach, and support B2B sales teams through the selling process. Grab a copy of Stop Killing Deals. Sponsorship Offers 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. 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.

  • #2043
    October 5 · 29 min

    How to Reach Decision-Makers When Selling to Enterprises | Erik Kostelnik - 2043

    125 billion B2B emails go out every single day, and that number is exactly why decision-makers have stopped noticing any of them. This one is coming from the archives, and honestly it feels even more relevant now than when it first aired, because reaching the right person inside an enterprise has only gotten harder since. Erik Kostelnik, founder and CEO of Postal, joined me to break down why reaching enterprise buyers has gotten so much harder and exactly what sales reps need to do differently to cut through that noise. Why Decision-Makers Have Gone Numb to Outreach The real problem isn't that buyers are unreachable, it's that everyone selling to them is running the exact same automated plays, the same email sequences, the same LinkedIn messages, and the same call cadences. With roughly 125 billion B2B emails sent daily, that volume has hit a critical mass where prospects develop a visceral reaction to anything that looks like a template, so the content itself stops mattering. Even internal teams at the companies you're targeting are often running similar outreach sequences to their own prospects, which means the people you're emailing recognize the exact playbook you're using. Touches Have Doubled, and So Has the Timeline The old rule of five touches over 30 days to get a yes or no has shifted, and the better target now is closer to 10 touches spread across 60 days. That shift ties directly to buyer behavior during 2020, when prospects were slower to respond and more hesitant to commit, which stretched out both the number of attempts needed and the overall timeline. Reps need to stop treating the five-touch, 30-day sequence as a fixed rule and instead build in enough room for buyers who need more time and more contact before they'll engage. Personalization Beats Automation at Scale The fix is to throw out the generic, templated sequence and go back to persona-based selling, meaning reps need to understand what a specific buyer actually cares about before reaching out. Postal's own approach treats direct mail and gifting as a real part of the sequence now, not an afterthought, because a handwritten note or a physical touchpoint still converts at a noticeably higher rate than another email. The goal is to automate the offline channel the same way sales teams already automate email, so a gift, a direct mail piece, a LinkedIn touch, and a phone call all carry the same consistent message instead of feeling disconnected. What a Real Outreach Sequence Looks Like For C-level targets, a strong sequence opens with a gift email, something like offering a relevant book with a short personal note, sent as part of a tracked outreach flow. If the prospect doesn't accept that first gift, the sequence continues with a LinkedIn touch, a phone call, and a follow-up email, then repeats with a different offer, like a direct mail brochure, if the second attempt also goes unanswered. This entire offline sequence runs in parallel with manual, non-automated emails and genuine engagement with the buyer's social content, and teams that combine offline and online touches see at least double the engagement. Why the Funnel Itself Needs to Flex Right Now Break the funnel into three parts, top, middle, and bottom, and diagnose which part is actually slowing deals down before trying to fix the whole process at once. At the top of the funnel, differentiation is what speeds things up, since standing out from competitors running the same automated plays is what gets a reply in the first place. In the middle of the funnel, flexibility matters most, which is why Postal leans into free trials even though a 12-month agreement is the ideal outcome, because buyers need an easier way to say yes during an uncertain stretch. "If you're not getting the right results, try something different." — Erik Kostelnik Resources Connect with Erik on LinkedIn. Learn more about Postal, the gifting and offline engagement platform. Sponsorship Offers 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. 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.

  • #2042
    October 2 · 24 min

    How I Handle Every Price Objection | Donald C. Kelly - 2042

    “It’s too expensive” may be the answer a prospect gives you, but it may not be the reason they are saying no. The real issue could be that they do not see the value, they already have another solution, or they have another concern they have not told you yet. In this objection-handling conversation, I break down two ways to get past the surface response, find the real reason behind an objection, and connect your solution to what the prospect actually values. The Real Reason Behind a Price Objection A prospect who says a $100 water bottle is too expensive may not really have a problem with the $100. They may simply be comparing it to a $10 bottle and not seeing what makes the more expensive option worth it. The value changes based on the buyer. For someone working outside in South Florida, a bottle that keeps water cold all day, has a built-in filter, and reduces trips away from a job site can solve problems that a cheaper bottle does not. That is why dropping the price is not always the answer. If the prospect does not see the value at $100, they may still not see it at a lower price. The salesperson's job is to find out what matters to that specific buyer and connect the solution to that need. Use the Socratic Method to Get to the Root Issue The Socratic method uses questions to help prospects think through their own problems and understand why a solution may be in their best interest. The questions should not be random. They should focus on the prospect's challenge and help uncover what is behind the first objection. A prospect may start with “I can get a water bottle for $10.” Keep asking questions and you may discover that the cheaper bottle means buying more water, buying ice, leaving the job site, and losing time that could have been spent quoting more work. Thank the Prospect Before You Challenge the Objection The first step is to thank the prospect for raising the concern and show genuine empathy. A $100 purchase is a bigger decision than a $10 water bottle, so the concern deserves to be taken seriously. From there, ask what they mean when they say it is expensive. Are they comparing it with another product? Have they never paid that much for a water bottle? Or do they simply believe the product is not worth $100? Those questions help reveal what the prospect is really thinking instead of forcing the salesperson to guess. Once the real concern is clear, the salesperson can educate the prospect around the value they were not seeing. Turn Lost Time Into a Business Case The water bottle example becomes more valuable when the conversation moves from the product itself to the time it can save. A construction worker who has to leave a job site for water or ice is losing working time. If that person can get even 30 minutes back in the day, that time could be used to quote more jobs. When one new job is worth thousands of dollars, the value of the solution looks very different. The salesperson is no longer selling a water bottle. They are selling convenience, time, and the chance to create more revenue. The same principle applies to other products and services: find the business problem behind the feature and show the prospect what solving it is worth. The Menu Method Gives You a Shortcut The second approach is the Menu method. Instead of asking a long series of questions, give the prospect a few common reasons other buyers have raised the same objection and ask if one applies to them. The options should come from real sales conversations. For example, the prospect may think the product is too expensive because it will not last, because they already have another solution, or because they are not interested in working with the company. This gives the prospect an easier way to explain what is really stopping them without having to come up with the answer from scratch. If none of the options apply, that is useful too. Ask them to explain what the real issue is and keep digging. Make the Prospect Empty Out Every Objection A prospect may have more than one concern. They might start with price and then reveal that they also think the product is fragile. That is why asking, “Is there anything else?” matters before moving into the solution. The goal is to get every concern on the table. Once the prospect has explained everything, you can address each issue instead of solving one objection and discovering another later. The approach is simple: find the root cause, explain how your solution addresses it, and then give the prospect a clear reason to believe the result is possible. Use Proof Before You Ask for the Sale After uncovering the objection, the next step is to educate the prospect and use a testimonial or case study from someone with a similar problem. One example in the conversation involves a company that bought the bottles for its team because employees were leaving job sites to get water. Those trips were linked to accidents, lost time, and other problems. The company saw roughly $300,000 in value from keeping its team on site, reducing accidents, getting more work done, and dealing with fewer health-related problems. That kind of proof can change the way a prospect sees the purchase because the conversation is now tied to a result they care about, not just the features of the product. Start Small Instead of Asking for the Whole Deal Once the value has been established, there is no need to ask the prospect to make the biggest possible commitment immediately. Instead of asking a company to buy 50 bottles for its entire team, start with one or two and let them see what happens. If the solution produces the result discussed, there is a clear reason to expand the purchase. The same approach can work with software, licenses, professional services, and other offers. Give the prospect a way to test the solution instead of asking them to take a large risk. The smaller commitment can make it easier for the prospect to move forward while giving you a chance to prove the value. "You don't need to talk about all the features. If you could just get help them with understand the one feature or one offering, one solution that can best help them, then money in the bank all day long." — Donald C. Kelly Sponsorship Offers 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. 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. 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.

  • #2041
    September 28 · 23 min

    How to Future Proof Against Getting Ghosted | Donald C. Kelly - 2041

    Nearly half of all B2B sales conversations end with no decision at all, and that number keeps climbing. This solo episode breaks down the discovery call framework built over years of carrying a bag as a software sales rep, now taught to clients to stop deals from going quiet. The Real Cost of No Decision A study of 2.5 million sales conversations by Matthew Dixon and Ted McKenna found that 40 to 60 percent of B2B deals end in no decision, not a loss to a competitor, just silence. Of those no-decision deals, 44 percent come from the prospect of sticking with their status quo, while the other 56 percent come down to indecision and analysis paralysis. Step 1: Build Rapport With Something That Matters to Them Small talk gets replaced with something specific and current about the prospect's business, like a recent win or a stat about their market share, so the conversation centers on them, not the seller. This shows the prospect that homework was done before the call, and it gets them talking about something they're proud of right from the start. Step 2: Set the Rules Before You Play the Game Early in the call, the prospect hears that the last five minutes are set aside to make a decision together, whether that's moving forward or agreeing it's not a fit. The prospect also gets permission to end the call early if it's clear they're not a match, which takes off the pressure and builds trust instead of suspicion. Step 3: Run Discovery So They Talk More Than You Do Before anything gets demoed, the prospect is asked what they want to learn from the call, then asked what else, so the exact proof they need becomes clear. Data from Gong backs this up: sellers should talk 30 to 40 percent of the time while buyers talk 60 to 70 percent, and that ratio is what keeps a deal moving instead of stalling. Step 4: Use the Last Five Minutes to Get a Real Decision Every call closes with a menu of next steps for the prospect, like bringing in a technical stakeholder, so there's a clear path forward instead of a vague "let me think about it." Getting the prospect's direct cell number and permission to text also gets added in, which makes it much harder for a deal to quietly disappear. "Set the rules before you play the game." — Donald C. Kelly Resources Learn more about the research behind this episode: jolteffect.com Sponsorship Offers 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. 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. 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.

  • #2040
    September 25 · 30 min

    Selling a Must-Have vs. Nice-to-Have: How to Win in a Competitive Market | Mark Van Oppen - 2040

    Selling a must-have product sounds easier than selling a nice-to-have. But even when your solution is critical to a customer’s business, you still have competitors fighting for the same deal. So, what makes a buyer choose you? In this episode, I talk with Mark van Oppen, CRO of SecureAuth, to talk about what it takes to sell a must-have solution in a competitive market. Selling a Must-Have vs. a Nice-to-Have Mark explains why sellers should first identify whether their solution is truly critical to their ideal customer. A product should solve a real business problem rather than forcing urgency where none exists. Finding the right Ideal Customer Profile (ICP) can determine whether a product becomes a must-have. Mark prefers selling solutions that are foundational to the customer’s business because they create stronger customer relationships. Why Buyers Ultimately Buy Trust Having a must-have solution does not automatically mean a buyer will choose you. When multiple companies can solve the same critical problem, trust becomes a major differentiator. Sellers build trust by doing what they say they will do. Trust also comes from demonstrating expertise and understanding the customer’s specific business problem. Every interaction should reinforce the buyer’s confidence that you can solve the problem. Understand the Customer's Business, Not Just the Industry Sellers need to understand how a problem appears inside a specific customer’s business. Different companies can experience the same technical problem in very different ways. Instead of using the same presentation for every prospect, sellers should tailor their conversations to the customer. Deep research helps sellers speak directly to the customer’s situation instead of making the customer explain everything from scratch. This level of preparation can demonstrate expertise and build credibility. Use AI Without Losing the Human Side of Selling It's possible that AI-powered sales tools would simply hide lazy sales behavior. He later became a supporter of tools such as Gong, call recording, automated notes, and follow-up summaries. These tools can help strong sellers increase their effectiveness while reducing missed details. AI should support good selling habits, not replace attention, preparation, or customer empathy. Manual note-taking still matters when automated tools are unavailable. The Three E's: Energy, Excellence, and Experience The three qualities Mark considers when hiring: Energy: The enthusiasm and commitment someone brings to the work. Excellence: A demonstrated history of committing to and delivering high-quality work. Experience: Knowledge gained through time and exposure to a specific role or industry. Mark puts them in that order because he believes experience can be developed, while energy and a demonstrated commitment to excellence are harder to teach. The "Say-Do-Say" Approach According to Mark, the phrase “say-do-say” describes another way of building trust. First, clearly explain what you are going to do. Then, actually do it. Finally, show the customer what you accomplished. This creates a clear connection between the customer’s expectations and the outcome you delivered. It also helps sellers reinforce their credibility throughout the sales process. Using a Mutual Action Plan Mark’s team uses a Mutual Action Plan (MAP) during complex sales. The MAP includes: The customer's problem statement and pain points. A list of tasks that need to be completed. Stakeholders responsible for each task. Specific delivery dates. Progress updates as tasks are completed. A commercial review covering the business side of the deal. The goal is to create a shared plan where both the buyer and seller understand their responsibilities and can track progress together. Building Trust Through Execution A seller's job does not stop after making a promise. Following through on commitments gives the customer evidence that they can depend on you. Documenting agreements makes expectations clear and reduces confusion. Consistent execution becomes especially important when your product sits in the customer's critical path. Popular Quote: "The buyer ultimately buys trust from their vendor." — Mark van Oppen Resources Learn more about SecureAuth: secureauth.com Reach Mark van Oppen: mvanoppen@secureauth.com

  • #2039
    September 21 · 31 min

    Is It You or Your Product? The Truth About Product-Market Fit | Collin Stewart - 2039

    Product-market fit isn't a yes or no question, and treating it like one is what trips up most founders and sales leaders. That's the core idea Collin Stewart, co-founder and CEO of Predictable Revenue and host of the Predictable Revenue Podcast, brought to this episode, and it reshaped how I think about why some go-to-market motions take off and others stall no matter how hard the team works. Product-Market Fit Isn't Binary, It Has Strength Most founders treat product-market fit as something you either have or don't, which makes the conversation almost impossible, because any founder with paying customers can point to that as proof they already have it. Instead, Collin described product-market fit as existing on a scale, from barely there to overwhelming, which means two companies can both have "a product in market" while one sells at a fraction of the speed of the other. That distinction matters because it shifts the question from a debate over whether fit exists to a real conversation about how strong that fit is and what would make it stronger. The Uber Eats Story That Proved the Point Collin shared that his old cold email agency normally booked around ten meetings a month for a client using the same process and the same team. When a former client joined Uber to launch what's now Uber Eats and asked Collin's team to run the exact same playbook, that single campaign of a thousand outreach emails booked 327 meetings in one month. The rep running the campaign hadn't changed and the process hadn't changed, so Collin concluded product-market fit acts as a multiplier on go-to-market effort, and Uber's fit was roughly 33 times stronger than anything else his team had worked on. Strengthening Fit Starts With Customer Development Interviews The fastest way to raise the strength of your product-market fit is to run structured customer development interviews with your pipeline, your existing customers, and people in adjacent markets. The key question to ask is what problem you'd solve for them if you could solve anything, then follow it with two scoring questions: how satisfied are they with how they currently solve it, and how important is solving it to them. The sweet spot is a problem that scores high on importance and low on satisfaction, because a painful, unsolved, high-stakes problem is what founders should build around, not a nice-to-have improvement. Why Working Harder Without Direction Backfires Collin compared weak product-market fit to riding a tricycle with the brakes clamped down, where grinding out more calls and more outreach just burns energy without covering more ground. He said the instinct to just work harder is the wrong move, because a founder who pauses to fix the product and the direction first will out-pace a founder who never stops to check if they're racing toward the right finish line. For sales leaders specifically, Collin's advice is to track whether a consistent process with consistent inputs is producing results that are out of line with a rep's past performance, because that gap is the signal that the product, not the person, needs the fix. How to Build a Case When the Founder Isn't Convinced If a founder isn't open to hearing that product-market fit is weak, a sales leader should still go run customer development interviews across five or six verticals on their own. Because that data builds the case no argument alone can win. He stressed that every customer development call should end with booking the next call while you're still on the phone, since the entire feedback loop breaks down without that habit and waiting to follow up later multiplies the work. Collin kept a sticky note on his monitor that read "don't forget to book the meeting" for years, because that one small discipline is what turns a single interview into a repeatable feedback loop with a prospect. What to Do About Outbound When Fit Is Still Weak The first move when fit is weak is to keep sending customer development interview requests instead of sales pitches, because the goal at that stage is learning, not closing. He walks prospects through a loop that moves from a discovery interview, to feedback on a paper prototype, to feedback on an MVP, to the question of what it would take for them to pay, and finally what it would take for them to refer three friends. Collin was direct that this only works if you book the next touchpoint before the call ends, because without that step you lose the momentum and have to restart the relationship cold every time. Leadership Advice, Books, and Quotes Collin Stewart recommends The Terrifying Art of Finding Customers, his book on connecting customer development to sales. Which he describes as part how-to guide and part honest account of the mistakes he made building his own companies. Resources Connect with Collin Stewart on LinkedIn. Learn more about Predictable Revenue, the company Collin co-founded and leads as CEO. Check out Predictable.ai, Collin's newer tool for running plays like customer development and social listening; it's in beta, and interested listeners can email Collin at his first name at predictablerevenue.com for details. Subscribe to Collin's newsletter at foundersed.co for more on the book and his other projects. Grab a copy of The Terrifying Art of Finding Customers. Sponsorship Offers 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. 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. 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.

  • #2038
    September 18 · 34 min

    AI Didn't Kill Sales Strategy. It Exposed Who Never Had One | John Stopper - 2038

    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 Important AI 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 — 03:38 Knowing 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 Strategies The 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 solutions. Executives have revenue responsibilities too. A salesperson can prepare an executive with the person's profile, the situation, the message to communicate, and the information to bring back. AI can take more operational work off the team's plate. That creates more room for leaders to spend time with customers and support revenue-generating conversations. Salespeople Need to Become Strategists As AI makes more sales information and tactics available, the ability to create useful insight becomes more important. AI has reduced the advantage that once came from simply knowing sales tactics. Sellers need to know how to use information, not just access it. The goal is to tell buyers something they do not already know. Strategy determines what insight to deliver, when to deliver it, and who should deliver it. Human-to-Human Selling Still Matters AI and digital tools should not replace direct conversations with buyers. At minimum, sellers should use video calls when meeting in person is not possible. Direct conversations can help uncover what digital research misses. Meeting a buyer in person can build trust and show a willingness to make an effort. Sales still depends on human relationships, especially when decisions are complex. Key Quote from the Episode “AI has commoditized a lot of that advantage. So now to me, selling and strategy is about how can I tell them something they don't know?” — John Stopper Resources: John Stopper: johnstopper.com John's website also offers a free, no-obligation deal strategy report. Submit a company you are trying to sell to, and he will run it through his COMPASS system and provide a deal strategy report. Email: J Stopper at Northstore.com LinkedIn: John Stopper Sponsorship Offers 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. 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. 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.

  • #2037
    September 14 · 36 min

    Your Connection Rate Dropped 80% and Nobody's Talking About It | David Zeff - 2037

    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 COVID David'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 Client Whistle 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 Story Prospects 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 People David 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 It David'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 Do David'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 job." — David Zeff Resources Connect with David Zeff on LinkedIn. Visit Whistle to learn more about their outsourced sales development services. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers 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. 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. 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.

  • #2036
    September 11 · 28 min

    How to Know if Your Deal is Going South Sooner than Later | Andee Harris - 2036

    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 Offers 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. 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. 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.

  • #2035
    September 7 · 36 min

    Stop Selling and Help People Solve Their Next Biggest Problem | Keith Gillispie - 2035

    A former Marine who did eight combat deployments in eight years now spends his time teaching people to stop pitching and start asking better questions. Keith Gillispie, founder of REI Automated, left the Marines in 2020 to build a real estate investing and coaching business that's helped more than 1,200 people, with close to 580 of them closing their very first deal. He broke down exactly how he qualifies, questions, and consults his way to the close. Why "Selling" Is the Wrong Mindset (Stop Being House Horny) Keith's blunt term for pushy sellers: house horny, chasing the deal so hard that they force the wrong solution onto someone just to close it. His fix is simple: stop selling, and start asking great questions that guide the prospect to the answer on their own. He reviews sales calls with his own team every week, and the biggest issue he catches with newer reps is a used-car-salesman energy that shows up the moment they stop asking and start pitching. Qualify for the Right Industry First Keith gets over a hundred Facebook messages a day, and his team has to pre-qualify people before he ever gets on a call. A recent example: a rep flagged someone as "qualified" who actually wanted coaching on commercial real estate, which Keith doesn't teach at all. Same broad label, completely wrong fit. Even inside a niche that sounds close enough, being in the wrong specific industry wastes everyone's time. Qualify for the Right Problem: Your Core Competency Must Match Their Core Constraint Keith's rule: everyone has problems, but that alone doesn't make someone a fit. What he's good at has to be exactly what the prospect is bad at. He calls this matching your core competency to their core constraint. If there's no real gap for him to fill, there's no real reason for the two of them to work together. This is what separates a win-win engagement from a sale that shouldn't have happened in the first place. Qualify for the Right Money (Or Every Call Becomes Charity) Even with the right industry and the right problem, a prospect still has to be able to afford the solution, or the call turns into free coaching. Keith shared a recent example of two prospects who badly wanted to join his program but couldn't spend even $300, when his coaching runs into the thousands. He's direct with his own team about this: sending him financially unqualified leads turns every call into charity work, which isn't sustainable as a business, even though he's genuinely happy to hand out free value when it makes sense. Diagnose Before You Prescribe Keith estimates that more than half of the people who come to him think they know what they need, and they're wrong. His example: prospects ask for automation when they don't even have leads coming in yet, or don't know how to structure a deal. Automating a broken process just scales the chaos faster. He compares it to a patient self-diagnosing before seeing a doctor. The seller's job, like a doctor's, is to ask enough questions to find the real issue before recommending anything. Get Comfortable Asking Uncomfortable Financial Questions Keith walks straight into questions like current income, whether that number is gross or net, and total debt, early in a call, because he can't build a plan without knowing where someone actually stands. He compares it to Google Maps: you need a point of origin and a point of destination before you can build the route in between. Roughly one in twenty-five or thirty people push back on how direct these questions are. Keith's response is straightforward: if they can't handle these basic questions now, the program itself is going to be a rough fit. Build Yes Momentum With Small Asks Keith structures his qualifying questions to build what he calls yes momentum: each small, reasonable question makes the next one easier to answer. He starts broad, what do you do, how long have you done it, before narrowing into income, debt, and financial specifics, so the conversation earns its way to the harder questions instead of opening with them. That same sequence doubles as training. The financial questions he asks on a discovery call mirror the exact questions his students will later need to ask sellers and private lenders. Ask Questions, Don't Make Statements Keith's rule for himself: don't make a statement for the first 60 percent of any sales call, aside from short softening statements like "I'm glad you asked that." The only exception is a brief acknowledgment before turning right back around and asking another question. Whoever is asking the questions is steering the conversation, and Keith treats that as true for the entire first half of every call he runs. Never Fully Answer a Question Without Asking One Back Keith borrows from Socratic questioning: when a prospect asks a direct question, like how fast he can close on a house, answering too quickly and too specifically can blow up the deal in either direction. Instead, he gives a partial, honest answer, then asks a question that uncovers the real reason behind their question, like whether they need to move fast or need more time. That extra step means his eventual answer is actually calibrated to what the person needs, instead of a generic response that might scare them off or fail to meet an urgent situation. Become a Lifelong Student of Your Craft Keith has taken more than ten thousand sales calls over eleven years and still says the more he learns about sales psychology, the more he realizes he doesn't know. His advice for anyone serious about improving: invest in a coach or mentor who can review real calls and point out specific gaps, rather than trying to learn everything for free through trial and error. His framing: you'll pay for the lesson either way, either in money to a mentor, or in wasted time and missed opportunity learning the hard way. "People don't care how much you know until they know how much you care." — Keith Gillispie Resources Connect with Keith Gillispie on LinkedIn. Visit REI Automated to learn more about Keith's education, software, and coaching community for real estate investors. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers 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. 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.

  • #2034
    September 4 · 26 min

    Your Sellers Are Motivated By WAY More Than Money | Sindre Haaland - 2034

    37 reps who got the least recognition on one 153-person sales team averaged 62 percent quota attainment. The team average was 107 percent. That gap is the whole argument Sindre Haaland, CEO and founder of SalesScreen, makes for why comp plans alone don't explain sales performance. Why Identical Comp Plans Produce Wildly Different Results Sindre's core observation: two reps can work under the exact same comp plan and produce completely different results, which means money alone isn't the daily driver of performance. Comp plans set the structure and tell a rep what they need to do to get paid, but engagement is what determines whether they actually do it consistently. An engaged rep will outperform a disengaged one with the identical incentive on the table, every time. Know Your Sales Math Sindre's first question to any rep: have you actually broken your quota down into what you need to do today, not just what you need to hit by year end? Reps who treat sales as a series of repeatable, data-driven daily activities have a far more predictable path to their number than those relying on charisma alone. Even with a full pipeline of data, the numbers only matter if a rep has the motivation to actually execute the plan. That's the gap gamification is built to close. The Four Player Types on Every Sales Team Sindre borrows a framework from game theory to describe four types of sales reps: killers, achievers, explorers, and socialites. Killers are driven by being number one and seeing their name at the top of the leaderboard. Achievers care about personal bests, regardless of where they rank against everyone else. Explorers enjoy the process itself, testing new tools and new angles. Socialites, the majority of most sales teams, are driven by recognition, visibility, and feeling like their effort is seen. The TV and Music Moment That Changed Sindre's Career Sindre described watching a sales floor the first time his team replaced a whiteboard with TVs that played music and visuals every time a rep closed a deal. People were jumping on their desks. That reaction is what convinced him sales motivation itself, not another feature, was the real business to build. A rep's win becoming a shared, visible, celebrated moment does something a quiet bank deposit never will. Three Rules for Running a Contest That Moves the Needle Timing matters more than most leaders assume. Contests started on a Wednesday consistently outperform ones started on a Monday, since early-week motivation has usually faded by midweek. Shorter is better. Month-long contests tend to create a "valley of disengagement," with excitement in week one, a dead middle, and a scramble at the end. One-day sprints create urgency without the letdown. Change the format so more than the top performer has a real shot. A lottery-style contest, where every meeting booked or deal closed earns a ticket, gives the middle of the pack a genuine "I might actually win this time" feeling. Get Creative: Pairing, Envelopes, and the White Elephant Game Pairing a high performer with a lower performer on a team-based contest naturally creates coaching and mentorship, without ever calling it that. Simple physical mechanics work too: envelopes on a wall that reps can pick from after hitting an activity, some holding a dollar, some holding a bigger prize. Sindre's favorite: a white elephant style game where prizes range from real rewards to silly forfeits, and reps can steal from each other until the contest ends, creating genuinely memorable moments on the floor. The Recognition Stat That Proves the Point Sindre shared data from a 153-person sales team where they measured how often each rep received recognition in a month. The 37 reps who received the least recognition averaged 62 percent quota attainment. The team average was 107 percent. Recognition and quota attainment move together closely enough that Sindre treats recognition frequency as a leading indicator, not just a nice-to-have. Where to Start as a New Sales Leader Sindre's starting point for anyone new to this: interview your top performers and find out what they actually do every day, not just what the official process says they should do. Frequently, top performers are doing things nobody explicitly asked them to do, or doing an already-known behavior far more consistently than everyone else. Cross-check those behaviors against the rest of the team. Wherever the gap is real, that's where a leader's next contest or incentive should be aimed. "A motivated person will do better than a disengaged one, even with the same comp plan." — Sindre Haaland Resources Connect with Sindre Haaland on LinkedIn. Visit SalesScreen, the world's leading sales gamification platform. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers 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. 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. 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.

  • #2033
    August 31 · 31 min

    Beyond the Mail Merge: How to Master True Relevance in B2B Sales | Leslie Venetz - 2033

    Only 10 percent of sales messages actually explain why something should matter to the buyer. The other 90 percent are just decoration on a generic pitch. That stat comes from Leslie Venetz, who audits thousands of sales messages every year and just released her USA Today bestseller, Profit-Generating Pipeline. She broke down what real relevance looks like, and the exact method she uses to build it. What Relevance Actually Means (And Why Most Sellers Miss It) Leslie defines relevance simply: a message has to be relevant to the person receiving it, not to the seller sending it. The biggest problem she sees is that most outreach centers on the seller's process, product, and company goals instead of the buyer. When she audits sales messaging, and she reviews thousands of messages a year, only about 10 percent actually explain why a piece of information should matter to the prospect. The Mail Merge Era: When "Fake Personalization" Felt Like Magic Back around 2012, Leslie ran a basic mail merge strategy that felt groundbreaking at the time. Prospects were genuinely impressed just to see their name and company pulled into an email. That tactic hasn't disappeared. It's evolved into things like mentioning a prospect's new job title or congratulating them on a funding round. The problem is the same one it's always been: something can be true about a prospect without being relevant to them right now. Personalization Versus Relevance Leslie draws a clear distinction: personalization is a fact about the prospect. Relevance is why that fact should matter to them today. I shared my own experience of digging through my inbox after the pandemic and realizing most pitches weren't even relevant to my actual role, let alone my actual problems. The real gap, in Leslie's words, is that most sellers never get into the buyer's emotional state, the specific pressure a person is under right now, not just their job title or industry. The Earn the Right Philosophy: De-Centering Yourself From the Pitch Leslie's core philosophy is called Earn the Right: before asking for a meeting, a call, or a contract, a seller has to earn the right to that person's attention. That means shifting language away from "I'm an account executive at [Company] and we sell [Feature]" toward messaging built entirely around the buyer's specific situation and outcome. The shift shows up in something as simple as word choice. Leslie says the biggest difference she sees in client messaging is emails that stop being about I, we, and our, and start being about you and your. The Five-Filter Segmentation Method Leslie's starting point for anyone new to territory planning is the five-filter method: four firmographic filters plus one demographic filter, layered together to turn a broad list into a hyper-specific one. She recommends starting with the demographic filter first, since narrowing a title, like going from "IT executives" down to just "CIO," forces a seller to ask what that exact role actually cares about. That one change alone, narrowing from a broad title to a specific one, has increased reply rates by more than 12 percent for her clients. A Real Client Example: Narrowing a Healthcare IT List Leslie walked through a real example from a global software company: a list originally aimed at "IT executives in healthcare" got narrowed down using all five filters. The firmographic filters included US-only, hospitals specifically, revenue between 100 million and a billion dollars, and customer service departments over 100 people. They also added a signal: whether the hospital had missed a recent best-of list. That detail alone reframed the entire pitch around better patient outcomes and service rankings, instead of generic product features. Shorter Emails, Longer Cadences A common mistake Leslie sees even after sellers embrace outcome-focused messaging: trying to cram everything they want to say into a single email. Her fix is to trust the cadence. Spread the story about a buyer's likely outcomes across multiple touches instead of one dense pitch. That shift also means holding off on a hard call to action early in a sequence, and letting later touches carry more of that weight. Why "More" Isn't a Strategy When results slow down, Leslie sees most teams reach for the same lever: hire more reps, send more emails, make more calls. Her pushback is direct: more is never the answer on its own, because it skips the harder work of understanding who you're actually talking to. Good segmentation is what makes every other activity, calls, emails, cadences, actually worth doing in the first place. The Marriage of Art and Science in Sales Leslie pushes back on using AI as a way to fully remove the seller from the process. If a prospect is expected to give their time and attention to a reply, the seller owes them a message that was actually written with care. The science side is the data: confirming you're talking to the right person, at the right account, about the right thing. The art side is judgment: knowing that just because something is technically personalized, like mentioning a promotion, doesn't mean it's the most relevant or human thing to say next. One Thing to Do Right Now to Get More Relevant Leslie's starting point for any sales leader: audit your current sales messaging and count how often it uses I, we, my, and our instead of you and your. That audit gives you real data on how self-centered your outreach actually is, even if it doesn't feel that way from the inside. From there, use AI for research instead of mass automation. Learn what a specific persona at a specific type of account actually cares about, then build that into the message. "More is not a strategy." — Leslie Venetz Resources Grab Leslie's book, Profit-Generating Pipeline: A Proven Formula to Earn Trust and Drive Revenue. Visit Leslie's company, The Sales-Led GTM Agency. Connect with Andy Paul, Leslie's mentor and host of The Win Rate Podcast, on LinkedIn. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. 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.

  • #2032
    August 28 · 33 min

    How We 2x Sales Revenue & Reduce Sales Cycle By 50% | Pieter Leenhouts - 2032

    Imagine doubling your close rate and cutting your sales cycle in half. That's not a hypothetical. It's exactly what Pieter Leenhouts and his team did at Tax Guard, a Cogency Global company that sells to banks and financial institutions. Pieter walked me through exactly how they pulled it off, and it wasn't magic. It was math, structure, and a relentless focus on the front end of the pipeline. Why Their Sales Cycle Was So Long To Begin With Tax Guard's solution was new to the financial institutions they sold to, so reps had to spend real time educating buyers before those buyers even understood why they needed it. That education requirement, combined with deals that stalled out with the wrong contacts, created a long sales cycle and a lower close rate. Fixing it started with the pipeline itself, not with pushing reps to work harder. Give Every Rep the Right Size Pipeline, Not Just More Deals Pieter's team found that around 120 opportunities was the right pipeline size for most of their account executives, though the number flexes based on how efficient a rep is. Instead of leaving reps to self source every opportunity, the team loads a portion of that pipeline for them, so reps spend more time working real opportunities and less time hunting for net new business. Their market of five to ten thousand financial institutions is well defined, which makes it possible to plan pipeline size with real precision instead of guessing. Split the Pipeline: 70 Percent Pre-Handraiser, 30 Percent Post-Handraiser Of those 120 opportunities, about 70 percent sit in the pre-handraiser stage, where reps are still working to connect with people. The remaining 30 percent sit in the post-handraiser stage, where there's already an active, ongoing conversation with the customer. That split keeps reps focused on outreach without starving the deals that are already moving. Marketing and Sales Load the Pipeline Together Pieter is careful to point out that loading the pipeline isn't a sales-only effort. It's a collaboration between sales leadership and marketing leadership. Marketing helps identify and prioritize which accounts and departments actually fit where Tax Guard's solution applies. That partnership is part of why the team can hand reps a healthier mix of fast cycle and slow cycle opportunities instead of leaving it to chance. Why They Kept AEs on the Full Buyer Journey Instead of Handing Off to BDRs Because their solution requires ongoing education, Pieter's team decided against using BDRs or SDRs to book appointments and hand off to AEs. The same person a buyer starts talking to needs to stay with them as a trusted advisor through the entire education process. Pieter is clear that this only makes sense because of how complex and unfamiliar their solution is. A more transactional sale can absolutely work with a BDR handoff. The Cadence: 17 Touches Over 70 Days Each opportunity in the pipeline follows a defined cadence, roughly 17 touches over 70 days, with three to five contacts tied to each account. That structure turns follow-up into a math exercise. Once you know the number of opportunities, steps, and contacts, you know almost exactly how many activities a rep needs to complete each day. The cadence isn't automated. Reps still show up and do the work themselves, which keeps the process personal instead of robotic. Personalization Is What Makes the Math Work Pieter gets five to six hundred pitches a day himself, so he knows exactly what gets ignored: generic, unpersonalized outreach. His team uses AI to gather background information quickly, but the personal touch, referencing where someone went to school or what they care about, still has to come from the rep. That combination of structure and personalization is what actually breaks through the noise instead of just adding to it. How They Catch Reps Who Are Gaming Activity Numbers To catch reps who rack up huge activity numbers without real substance, like hanging up before voicemail or blasting the same email to everyone, Pieter's team looks past raw activity totals. They review call recordings and email engagement to see whether real conversations are actually happening, not just whether the activity got logged. The goal isn't to catch people doing something wrong. It's to find the reps who are getting real engagement and figure out what they're doing differently so the whole team can replicate it. Weekly and Monthly Rhythms Keep the Team Accountable Every rep gets a weekly one on one that covers both big strategic issues, like what's happening in the market or with competitors, and specific opportunities that need a plan to close. Once a month, Pieter's team reviews the front end metrics as a group: how many people are in cadence, how many emails are opening, how many real conversations are happening. They also track Net Promoter Score to measure how the sales experience actually felt to the buyer, not just whether a deal closed. Their Tech Stack: Salesforce, Gong, Gong Flows, and Delighted Salesforce is their core CRM, and Pieter says most of what makes it powerful is what gets plugged into it. Gong records and analyzes sales conversations, which lets the team track things like how often pricing objections come up and coach reps faster than they could otherwise. Gong Flows adds structured outreach sequences with AI built in, and Delighted measures NPS so the team can see how the buying experience felt from the customer's side. The Numbers Pieter's Team Watches Every Week Close rate and pipeline velocity are the two headline numbers Pieter checks first, since they show whether the whole system is working. Underneath those, his team tracks how long deals sit in each of their seven pipeline stages, with alerts when something sits too long. They also watch the quality of the opportunities reps are given and how well each rep prospects into the right people, since strong activity numbers mean nothing if they aren't pointed at the right accounts. "Activities create opportunities, opportunities create sales. The only thing we control is our activity level." — Pieter Leenhouts Resources Connect with Pieter Leenhouts on LinkedIn. Learn more about Tax Guard, a Cogency Global company. Keep track of your sales activity and boost your results with the Prospect Pro sales tool. Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals. Visit Blue Mango Studios for help creating podcast production content. Join our LinkedIn cohort and learn to prospect the right way. Sponsorship Offers 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. 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. 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.

  • #2031
    August 24 · 29 min

    Are You Too Nice to Close the Deal? | Connie Kadansky - 2031

    Connie Kadansky was a highly motivated, highly goal-oriented salesperson, and she was still taking naps at two in the afternoon instead of prospecting. That contradiction sent her down a research rabbit hole that turned into a 29-year career studying sales call reluctance. Connie broke down for me why being too nice is one of the most expensive habits a seller can have, and what to do about it instead. The Napping Salesperson Who Became a Call Reluctance Expert Years ago, Connie was a highly motivated, highly goal-oriented seller who kept finding herself taking naps at two in the afternoon instead of prospecting. That contradiction led her to a book called The Psychology of Sales Call Reluctance, written by two behavioral scientists, and eventually to their fear-free prospecting workshop and eight weeks of coaching. She's been a licensee with that research organization for 29 years, and still uses the same assessment to diagnose call reluctance in sellers today. Being Too Nice Is a Real, Named Problem: The Yielder Connie's research identifies 16 types of sales call reluctance, and the most costly one is called the yielder. Yielders are great with people. They can open a conversation and build rapport easily, but they struggle to move a conversation past that rapport into the next real step. The belief driving it: the nicer I am, the more they'll like me, and the more likely they are to buy. Connie is direct that this isn't true, and it leads yielders to back off and hope the prospect closes the deal for them. The Three Types of Yes You'll Hear in a Sales Conversation A committed yes means the prospect is genuinely engaged and agreeing to a real next step. A counterfeit yes sounds positive but has nothing behind it, things like "send over some information" or "call me in two months." A confirmation yes happens when a prospect confirms something concrete, like who else is involved in the decision. Yielders are the most likely to accept counterfeit yeses at face value and build their forecast on them. Nice Versus Kind Aren't the Same Thing Connie draws a clear line: nice is agreeable and comfortable. Kind is asking a question the prospect has never considered, and actually working to solve their problem. Her definition of selling is solving people's problems for a profit, and staying kind means keeping the conversation pointed at the actual problem instead of just keeping things pleasant. If there's no real problem to solve, no amount of niceness changes that. The relationship alone was never going to be what closed the deal. Stop Overinvesting in Rapport Spending too much time on small talk, weather, sports, general connection, feels productive to a yielder, but it isn't what closes business. Connie points out that most people don't buy because a rep shares their taste in baseball. They buy because the rep solved a real business problem. Her fix: be friendly, be kind, but get to the point quickly, and have real, prepared questions ready to move the conversation rather than lingering in rapport building. Understand the Objection, Don't Just Try to Overcome It Connie's approach breaks from the standard sales training instinct to power through and overcome objections. Instead, she teaches getting curious about the objection itself. Yielders tend to treat objections as conflict, and conflict is exactly what they're trying to avoid, so they steer around it instead of naming it directly. Her technique borrows from Chris Voss's negotiation work: label the emotional component behind the objection out loud, which takes practice but opens up a much deeper conversation. Get Curious to Go Beyond the Surface-Level Problem It's easy to stop at a surface-level answer, like a prospect saying they need a new CRM, and move straight to a quote without digging further. Connie recommends calibrated what and how questions, prepared in advance, to get past the surface answer to what's actually driving the frustration. Her rule of thumb: curiosity isn't intellectual, it's emotional. The best sellers can set aside their own agenda long enough to keep asking, sometimes with something as simple as "what else?" How to Actually Fix This in Yourself Connie's advice starts with getting genuinely curious as a practice, not just a technique, including reading about curiosity and noticing how much more interesting curious people's lives tend to be. She recommends writing the actual inner dialogue down on paper: naming the specific fears behind the hesitation, like fear of pushback on price or fear of a difficult implementation. The goal isn't to lose the warmth that makes yielders likable. It's pointing that same personality at pulling out the truth instead of avoiding it. "My definition for selling is solving people's problem for a profit." — Connie Kadansky Resources Connect with Connie Kadansky on LinkedIn. She publishes an article on sales call reluctance about once a week. Visit Connie's company, Exceptional Sales Performance, to learn more about her coaching and the SPQ assessment. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers 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. 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.

  • #2030
    August 21 · 34 min

    Stop Overthinking Your Sales Calls (Do This Instead)" | Adam Lowther - 2030

    An architect plans every brick before laying one. An archaeologist starts digging and adjusts based on what turns up. Adam Mark Louther says most sales reps try to sell like architects when the job actually calls for an archaeologist's mindset. Adam built his first sales skills knocking on doors selling exterior cleaning services, and today he coaches founders and sales teams on turning conversations into paying clients. We talked about why overthinking kills deals, how the first five minutes of a call sets the frame for everything after, and the two-call process he uses to close more business. Stop Overthinking and Take Action Adam's biggest message: sales gets overcomplicated. Most people already have enough information to move, but they stall out gathering more instead of acting on what they have. People stuck in analysis paralysis are the ones who need every detail mapped out before they'll take a single step, and that costs them in a fast moving environment like sales. The reps and leaders who win aren't the ones with the perfect plan. They're the ones who execute, look at the results, and adjust from there. Think Like an Archaeologist, Not an Architect Adam's framework, borrowed from his mentor: an architect needs total certainty before building, since every measurement has to be right before anything gets built. An archaeologist works the opposite way. They dig in one spot, see what's there, and adjust based on what they find, since nobody knows exactly what's underground until they start. Sales works like archaeology, not architecture. You have a general idea of where to focus, then you test, learn, and adjust instead of waiting for certainty that never comes. There's No One Right Sales Process Adam pushes back on the idea that there's a single correct sales methodology to follow, whether that's MEDDIC, Challenger, or anything else. What matters is consistently doing the fundamentals: finding the real issue, talking to the right person, and building enough value that price stops being the objection. Getting stuck choosing the "perfect" framework is its own form of analysis paralysis, and it keeps people from ever getting real reps in. The First Five Minutes Sets the Frame A call handled poorly in the first few minutes can cost the entire sale, because that's when the frame and the agenda get set. Whoever asks the questions controls the call. Without setting that frame early, a buyer with a strong personality will take over the conversation entirely. Adam learned this the hard way early in his career, watching experienced buyers steer his calls before he had a structure in place to prevent it. Three Parts of Opening a Call: Icebreaker, Frame, Agenda The icebreaker is genuine, unscripted small talk. It should feel like a normal conversation, not a routine, and it should be dropped if the other person clearly isn't in the mood for it. The frame reminds the buyer why the call is happening and how they got connected in the first place, since a call booked weeks ago often gets attended on autopilot without that context. The agenda tells the buyer exactly how the call will run, before a single discovery question gets asked. Adam explicitly tells prospects he'll ask questions first, then invite them to a second call if it's a genuine fit. Always Book the Next Meeting From the Meeting Adam uses what he calls BAMFAM, book a meeting from a meeting. If a prospect says they'll "arrange something" later, that call almost never happens. The second call needs to get booked on the calendar before the first call ends, since people get busy and forget otherwise. This is a small habit that protects momentum on every deal in the pipeline. Build a Personalized Game Plan Before the Second Call Between the two calls, Adam reviews the discovery call transcript and notes, then builds a plan using the prospect's own language and specific pain points. On the second call, he walks through that plan, framed as free coaching rather than a pitch, which is what makes prospects want to see more detail instead of feeling pitched to. The transition into the actual offer is simple: he tells them the plan isn't quite as simple as the summary, offers to show them more detail if they want it, and lets the prospect self-select into hearing the pitch. How to Actually Start Taking Action Adam's advice for anyone stuck in analysis paralysis: first figure out what's actually driving the hesitation, whether it's fear of rejection or something else, since you can't fix what you haven't named. After that, find the smallest possible action you can take today, not the biggest. Small wins build confidence, and that confidence compounds until the actions that felt out of reach start to feel normal. "Think about what is the smallest action you can take today. Gain confidence from every action you take, and it compounds." — Adam Mark Louther Resources Connect with Adam on Instagram: @adammarklouther. He offers a free 45-minute discovery call to talk through where your sales process may be losing deals. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers 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. 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.

  • #2029
    August 17 · 34 min

    People Buy You | Jordan Harbinger - 2029

    Your prospect isn't only buying the product or the price. They're buying you. That's the idea behind one of Jordan Harbinger's most popular keynotes, and it's why we're pulling this archive conversation back out. Jordan went from a bored kid who got into trouble to a Wall Street attorney to the host of one of the biggest interview podcasts around. And the thread running through all of it is relationships. The principles here haven't aged a bit. This episode explores all of it. Why Jordan Started Studying This in the First Place Jordan assumed people with strong networks were either born into them or got there through some elite club or school connection. That changed on Wall Street, when he realized everyone around him was just as smart and just as hardworking. Being the smartest or the hardest worker in the room was no longer a real advantage. A partner at his firm who was rarely in the office turned out to be out generating business through relationships, not hiding from work. That single conversation changed how Jordan thought about his entire career. Relationships Are the Foundation, Not the Finishing Touch Jordan compares skipping networking to building a house without a foundation. You don't add the roof and windows first and figure out the foundation later. It doesn't work that way with a business or a career either. The most common mistake people make is pushing networking to later. Entrepreneurs tell themselves they'll focus on relationships once the website, the product, and the ads are all dialed in first. By the time most people realize they skipped it, it's already cost them. Jordan points to the classic moment of watching someone else get promoted to become your boss, when the real difference often wasn't skill. It was who built relationships along the way. Skip Networking Events That Aren't Curated Jordan's rule: avoid any networking event open to the general public. If anyone can walk in, there's a strong chance the room is full of people looking to take, not give. He describes his own experience at open mixers: a rotating cast of financial planners, car salesmen, and life coaches all working the room for a stale cookie and a captive audience. A curated event, like a real chamber of commerce meeting full of actual business owners, is worth your time. If you can't get invited to one, Jordan's advice is simple: build your own. Why Giving First Actually Scales Better Than Closing Jordan contrasts the old "always be closing" mindset with what he calls ABG, always be giving. Closing limits you to the handful of people in a room who happen to need exactly what you sell. Giving opens up nearly everyone in the room, because you're looking for what they need instead of trying to match them to your offer. Jordan's example: instead of pitching graphic design services to someone who doesn't need them, he'd ask what they're working on, then connect them to someone in his network who can genuinely help. That's scalable in a way that chasing a single sale never is. Don't Keep Score Giving only works if it's not secretly transactional. Jordan warns against what he calls keeping score: doing favors while quietly expecting something back later. He illustrates this with a story about a friend who drove a neighbor to the airport repeatedly, expecting it to eventually turn into a relationship, then got upset when it didn't. The resentment showed up in every interaction afterward, and the other person had no idea why. The same pattern shows up constantly in sales. A rep gives a free tip, then pitches the very next interaction. That turns a relationship into a quid pro quo, and people can feel it immediately. Dig the Well Before You're Thirsty Jordan's core advice: build relationships long before you need them. Waiting until you need a job or a referral to start networking is like keeping a spare tire in the trunk and only thinking about it after you're already stuck on the highway. His practical exercise: write down the ten people you'd call if you lost your job tomorrow, then reach out to them this week, while you don't need anything from them. That single habit, reaching out with nothing to ask for, is what separates people with a real network from people scrambling to build one under pressure. "You have to give first, not just because it's a great Zig Ziglar quote or a Brian Tracy principle. It's because it's logistically easier for me to find a need that you have than it is to match a need you have with a service that I provide." — Jordan Harbinger Resources Listen to The Jordan Harbinger Show, wherever you get your podcasts, or visit JordanHarbinger.com. Check out 6 Minute Networking, Jordan's free course on building real relationships. Join our LinkedIn cohort and learn to prospect the right way. Visit Blue Mango Studios for help creating podcast production content. Sponsorship Offers This episode is brought to you in part by HubSpot. You don't become the world's most valuable women's sports franchise by accident. Angel City Football Club did it with a little help from HubSpot, unifying their website, email, and fan experience in one platform, and growing their database 300 percent in two years. Visit hubspot.com to hear how HubSpot can help your team grow better. This episode is brought to you in part by LinkedIn. LinkedIn Sales Navigator uses AI-powered recommendations and real-time account insight to help you spend less time searching and more time selling, all powered by LinkedIn's network of over 1.2 billion professionals. Try it free for 60 days at linkedin.com/sell. This episode is brought to you in part by Blue Mango Studios. Imagine using a podcast as a lead generation source, attracting your ideal customer while getting qualified leads. Find out more at bluemangostudios.com. Credits The Sales Evangelist Podcast is created by the Sales Evangelist Sales Training Organization. It is produced by TSE Studios. Our podcast production manager is Nancy Paul. Our audio engineer is Jerchin Obyale. Our video engineer is Dasan Kunado. Guest management is done by Jill Vito and Christy Vertus. Our content writer is Carlisa Galbreath. Our graphic designer is Urvish Savalia, and Donald C. Kelly is your host and executive producer.

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