The Sales Evangelist: Sales Training|Speaking|Business Marketing|Donald Kelly

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 ItKristie'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 Hybr

"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 ConfidenceSystematic 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

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 DealsDeals 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 t

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 OutreachThe 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

“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 ObjectionA 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

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 DecisionA 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 ThemSmall 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 pro

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-HaveMark 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 TrustHaving a must-have solution does not automatically mean a buyer will choose you.When multiple companies can solve the same critical problem, trust

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 StrengthMost 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

AI is changing sales fast. But is it actually replacing salespeople, or is it exposing the sellers who never developed real strategy skills? That’s the question I explore in this conversation with John Stopper.John and I get into the difference between sales tactics and sales strategy, why AI can sometimes give sellers the wrong picture of a buyer, and why getting closer to the people involved in a deal can make the difference between winning and losing. We also talk about how sales teams can use AI to identify deal risks instead of simply using it to write more emails.Why AI Makes Sales Strategy More ImportantAI can teach people sales tactics, but strategy requires a deeper understanding of the situation.Tactics focus on how to sell, while strategy focuses on who, what, when, where, and why.AI can help sellers execute many tactical tasks, but sellers still need to decide which approach fits the buyer and the situation.Strong sales strategy starts with understanding customers and what will actually compel the

Connection rates have dropped roughly five times since before COVID.If ten percent of your calls used to turn into a conversation, you're probably closer to two now.David Zeff, CEO of Whistle, runs an agency that makes cold outreach work for 350-plus B2B clients, and he broke down exactly what's changed, what hasn't, and the parts of outbound most people are too embarrassed to actually do.Why Connection Rates Have Collapsed Since COVIDDavid's headline stat: connection rates have dropped roughly five times since the early 2010s. If a rep used to get a conversation on ten percent of calls, that number is closer to two percent now.That drops compounds. Fewer conversations means fewer meetings booked from the same amount of effort, cutting a rep's effective output roughly in half even before factoring anything else in.He points out that most investors and boards setting revenue benchmarks don't actually understand how much this single number has shifted, which means the targets built on top of it are often unreal

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 dea

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 FirstKeith gets over a hundre

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 ResultsSindre'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 MathSindre'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 hav

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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 WithTax 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 DealsPieter's team found that around 120 opportunities was the right pipeline size for most of their account executives, though the

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