The Sales Evangelist

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 Hybrid TeamKristie'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 VerifyKristie 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 ItKristie 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 BuiltHer 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 AgentKristie'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 UncheckedFirst, 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 UsKristie 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 MeansKristie 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 FluentKristie'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 JonesResourcesConnect 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.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

"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 later stage possible.Step One: Always Be Learning, Not Always Be ClosingThe 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 ReputationConsistent, 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 ConversionsSocial 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 EngineMost 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 CoexistA 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 BurgessResourcesConnect with Jimmy Burgess on LinkedIn.Check out The Real Estate Sales Podcast, where industry experts share strategies that apply well beyond real estate.Sponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

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 type instead of the specific environment is a mistake that shows up later in lost deals.Why Buyers Don't Decide RationallyThe 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 SellerThe 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 MadeThe 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 SurviveA 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 BronténLeadership Advice, Books, and QuotesGeorge 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.ResourcesConnect 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 OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

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 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 TimelineThe 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 ScaleThe 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 LikeFor 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 NowBreak 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 KostelnikResourcesConnect with Erik on LinkedIn.Learn more about Postal, the gifting and offline engagement platform.Sponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

“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 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 IssueThe 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 ObjectionThe 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 CaseThe 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 ShortcutThe 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 ObjectionA 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 SaleAfter 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 DealOnce 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. KellySponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

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 proud of right from the start.Step 2: Set the Rules Before You Play the GameEarly 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 DoBefore 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 DecisionEvery 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. KellyResourcesLearn more about the research behind this episode: jolteffect.comSponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

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 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 IndustrySellers 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 SellingIt'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 ExperienceThe 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" ApproachAccording 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 PlanMark’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 ExecutionA 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 OppenResourcesLearn more about SecureAuth: secureauth.comReach Mark van Oppen: [email protected]

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 is and what would make it stronger.The Uber Eats Story That Proved the PointCollin 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 InterviewsThe 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 BackfiresCollin 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 ConvincedIf 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 WeakThe 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 QuotesCollin 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.ResourcesConnect 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 OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

John Stopper, sales strategist and creator of the Compass operating system, explores why AI makes real sales strategy more vital. They unpack tactics versus strategy, using AI to uncover deal risks, verifying buyer research, and getting closer to the people who can influence or derail complex B2B purchases. They also discuss executive involvement, internal bridges, and why human trust still matters.

Connection rates have dropped roughly five times since before COVID.If ten percent of your calls used to turn into a conversation, you're probably closer to two now.David Zeff, CEO of Whistle, runs an agency that makes cold outreach work for 350-plus B2B clients, and he broke down exactly what's changed, what hasn't, and the parts of outbound most people are too embarrassed to actually do.Why Connection Rates Have Collapsed Since COVIDDavid's headline stat: connection rates have dropped roughly five times since the early 2010s. If a rep used to get a conversation on ten percent of calls, that number is closer to two percent now.That drops compounds. Fewer conversations means fewer meetings booked from the same amount of effort, cutting a rep's effective output roughly in half even before factoring anything else in.He points out that most investors and boards setting revenue benchmarks don't actually understand how much this single number has shifted, which means the targets built on top of it are often unrealistic from the start.The Four Things Whistle Screens For Before Taking a ClientWhistle turns away clients the way a lawyer might turn down a case they can't win. David treats a signed client as the start of the real work, not the finish line.First: does the founder actually know their ICP? If they're still deciding between multiple very different buyer types, that's a major warning sign.Second: is the total addressable market big enough to support a real sales motion, since a market of a few hundred accounts with multi-year sales cycles isn't a fit for most outbound efforts.Third and fourth: is there real marketing support behind the sales effort, and does the product have any real moat, since neither one used to be a dealbreaker a decade ago the way they are now.The New Risk: Can Your Prospect Just Build It Themselves?David's newest red flag: prospects increasingly ask themselves whether they could just build a simple version of the product using AI tools instead of buying it.His own team has looked at some clients' products recently and had the same reaction: this looks like something built quickly with AI, which means the prospect is likely to think the same thing.Sellers need a clear, early answer to that question, since it's showing up at the very top of the funnel now, not just at the negotiation stage.Why Cold Email Copy Isn't the Real StoryProspects often ask David to see a sample of Whistle's email copy, expecting the wording itself to explain the results.His answer is always the same: seeing the email is like seeing the cheese and asking how that made the pizza. The copy alone leaves out everything that actually got the message opened and read in the first place.Highly personalized details, like referencing someone's favorite sports team, used to work well on their own. David is direct that this stopped being enough years ago, even though it still gets attention on LinkedIn as a screenshot-worthy tactic.Stop Separating the Brand From the PeopleDavid points to Gong as the company that got this right early: during the shift to remote work, they made individual employees visible instead of hiding behind the company logo, including putting reps on billboards.B2C brands have leaned on individual personalities for a long time. B2B is only catching up to that now, and companies that keep everything behind a logo are giving up a real advantage.Donald shared a reference point from a past guest at Chili Piper, who said roughly half the deals in their pipeline had some connection to her personal LinkedIn activity, not because she was directly involved in every deal, but because buyers had engaged with her content somewhere along the way.Build Community Before You Need ItDavid's third layer, beyond the basics and personal branding: building some form of community or network around your business, even a small one.A simple example from one of his own clients: a marketing VP asked if Whistle could bring their clients together to trade notes, which turned into a referral network of consultants and adjacent service providers.It doesn't have to be a massive branded community. Even something as basic as a small referral relationship, a shared cause you donate to together, or a network of people adjacent to your buyer who can talk about your space, counts and compounds over time.The Free Tactic Nobody Will Actually DoDavid's final, deceptively simple tip: export your personal contacts from WhatsApp or your phone, write one honest message explaining what you do and asking for a referral, and send it to twenty people a day.His prediction is that most people won't actually do this, precisely because it's free, easy, and has no clever trick to hide behind if it doesn't work.He's currently running an open deal that came directly from this exact method, reaching out to a personal contact who referred him to someone else who's now moving through the sales process."We're in sales. You're always desperate. That's the job." — David ZeffResourcesConnect 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 OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.This episode is brought to you in part by the TSE Sales Foundation.Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.CreditsAs one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.