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!

  1. 2d ago

    4 Steps to Systematic Sales Growth

    "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.

    4 Steps to Systematic Sales Growth
  2. 5d ago

    The Top Three Issues Killing Your Sales Deals

    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.

    The Top Three Issues Killing Your Sales Deals
  3. Oct 5

    How to Reach Decision-Makers When Selling to Enterprises

    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.

    How to Reach Decision-Makers When Selling to Enterprises
  4. Oct 2

    How I Handle Every Price Objection

    “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.

  5. Sep 28

    How to Future Proof Against Getting Ghosted

    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.

    How to Future Proof Against Getting Ghosted
  6. Sep 25

    Selling a Must-Have vs. Nice-to-Have: How to Win in a Competitive Market

    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 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 Oppen Resources Learn more about SecureAuth: secureauth.comReach Mark van Oppen: mvanoppen@secureauth.com

  7. Sep 21

    Is It You or Your Product? The Truth About Product-Market Fit

    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.

  8. Sep 18

    AI Didn't Kill Sales Strategy. It Exposed Who Never Had One

    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 — 03:38Knowing how to throw every pitch does not mean you know which pitch to throw. A baseball pitcher may have four or five pitches available.The right pitch depends on the batter, pitch count, runners on base, and inning.Sales works the same way. The skill is not just knowing the sales playbook but knowing which strategy to use in the moment.Choosing the right strategy can improve your position, accelerate velocity, and compress time. The Principle of Reality: Don't Trust Every AI Answer AI can give both buyers and sellers information that does not accurately reflect the current situation. Buyers can use AI to research a salesperson or company before the first conversation.Sellers can also build their account research around outdated or incomplete information.A polished AI summary can create false confidence if it does not reflect what is actually happening.Sellers should verify their assumptions instead of treating AI research as unquestionable fact. How to Surface Reality With Better Questions The first sales conversation is an opportunity to check whether both sides are working from the right information. Ask the buyer what their AI research has shown them about your company, product, or you.Share what your research has shown you about their company and ask whether you have it right.Use the conversation to identify what is missing from your research.Verify the situation before choosing your sales strategy. Different Buyers Require Different StrategiesThe right message depends on the person you are selling to. End users often care about doing their jobs faster, better, or cheaper.Managers may care more about how a solution affects their team and the risks involved.Executives are more likely to focus on strategic growth and business outcomes.Sellers need to understand the buyer's role before deciding what value to emphasize. The Principle of Proximity: Get Closer to the Buyer “Proximity sells” because sellers need to understand the buyer's world deeply enough to bring useful insight. Proximity is not about becoming the buyer's friend.It means understanding the buyer's business and seeing things from both inside and outside perspectives.Sellers should get close to the people who can influence the deal, not only the person who can approve it.Outside experience can help sellers bring insights the buyer may not have considered. Find the People Who Can Say No A deal can have strong champions and still fail because someone else inside the organization has the power to stop it. Identify the people who may resist the purchase.Ask your champion who in the organization could have concerns about the solution.Reach out to those people directly instead of waiting for their objections to appear later.Address potential resistance before it becomes a deal-ending problem. Use AI to Identify Deal Risk AI can be useful when it helps sellers think through what could go wrong. Ask AI to research the people and roles that may resist a purchase.Identify possible objections and resistance points before they appear.Continue updating the research as the deal progresses because new risks can emerge.Use AI to help build a deal strategy around what could prevent the deal from closing. Bridging Strategy: Build Relationships Across the Account One salesperson should not have to carry every relationship in a complex B2B deal. Sales managers can connect with the buyer's manager.Product leaders can connect with the buyer's technical leaders.CEOs can connect with other executives when the situation calls for it.Each person can carry a message that matches their role and expertise.Multiple relationships can help both companies become more familiar with each other. Why Executives Still Have a Role in Selling Executive involvement can be part of the sales process, especially when selling complex 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, a...

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