Here is how I closed a 6-figure deal with humor | Kevin Hubschmann - 1967

show notes

What should you be posting on LinkedIn, and what should you avoid? In this episode, I share three LinkedIn posts sellers can use right away. Posting the right content on LinkedIn can help you book more appointments and grow your pipeline.Why You Should Be Posting on LinkedInIf you are not posting on LinkedIn, you are missing a real opportunity to stand out. Only a small percentage of users create content, which means authentic posts are far more likely to get noticed. Instead of worrying about being judged or feeling like you need to be an expert, I want you to see LinkedIn as a place to engage your niche market and start real conversations.Three Types of LinkedIn Posts That WorkMistakes and Lessons Learned: One of the easiest ways to create content is by sharing mistakes and lessons from your own experience. Talking about what went wrong and what you learned makes your posts relatable and builds trust. When you are honest and a little vulnerable, people are more likely to engage and respond.Personal Insights: You do not have to talk about sales all the time. Sharing personal insights like hobbies, challenges, or goals helps people connect with you as a person. Whether it is working on your golf game or focusing on better health, these posts humanize you and often lead to stronger conversations with prospects.Industry Trends and Data: Posting about industry trends or data gives your audience something valuable to think about. Share insights you are seeing in the field or information from reports you trust. When you consistently bring useful information to your network, you position yourself as a resource and stay top of mind with potential buyers."Thanks to the COVID era, people want to know you on a personal level. They want to see your personality online." - Donald KellyResourcesSign up for free and download the Sales Evangelist Tracker to monitor your sales KPIs, measure performance, and stay accountable to your daily activity.Join the LinkedIn Prospecting Course to improve how you use LinkedIn and book more consistent, high-quality sales appointments.Visit Blue Mango Studios for help in 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...

We’re a month into 2026, so there’s no time for rookie mistakes. In this episode, I’m breaking down 10 common mistakes sellers make and how to avoid them. Catching these early can help you set yourself up for success for the rest of the year.1. Not Having Enough Deals in the PipelineOne of the biggest mistakes I see is not having enough opportunities in the pipeline. I recommend carrying three to five times your quota in active deals to protect yourself when prospects go quiet or deals fall apart.&nbsp;When you consistently add new opportunities, your sales engine keeps moving even when the market shifts.2. Not Using LinkedIn EffectivelyToo many sellers are underutilizing LinkedIn as a prospecting and research tool. I encourage upgrading to Sales Navigator, multi-threading within accounts, and posting consistently.&nbsp;Staying visible helps you build familiarity and turn cold outreach into warmer conversations.3. Waiting Too Long to Involve StakeholdersRelying on a single champion is risky. Most B2B deals involve multiple decision-makers, so it’s important to identify and engage stakeholders early.&nbsp;LinkedIn is a great way to map the organization and start those conversations sooner.4. Skipping Daily ProspectingPipeline growth does not happen by accident. Prospecting needs to be a daily habit.Blocking time each day and testing different outreach windows helps create consistency and avoids feast-or-famine cycles.5. Lack of Planning and KPI TrackingPlanning your week and your day is non-negotiable. I recommend blocking time for prospecting and meetings, then tracking KPIs like calls, conversations, appointments, and closed deals.&nbsp;Reviewing these metrics helps you see what is working and where you need to improve.6. Ignoring AI ToolsAI is changing the way we sell. Tools for note-taking, research, and CRM updates can save time and reduce admin work. Testing AI solutions now helps you stay competitive.7. Not Asking for the Next AppointmentEvery meeting should end with a clear next step. I always leave a few minutes to schedule the follow-up so momentum does not stall.8. Missing Red FlagsHesitation around pricing or commitment should not be ignored. Address concerns early by asking direct questions before deals slow down.9. Not Going Deep Enough on ObjectionsSurface objections are rarely the real issue. Dig deeper to uncover what is truly holding the buyer back.10. Selling to the Wrong Pain PointBefore pitching a solution, make sure you understand the prospect’s real problem. When the pain is clear and validated, demos and proposals land much more effectively.“Don’t sell to the wrong objection or try to solve the wrong problem. Commit to going deeper, uncover the real reason behind the objection, and address that directly. That is your job, and it’s one of the most important things you do in sales.” - Donald Kelly&nbsp;ResourcesSign up for free and download the Sales Evangelist Tracker to monitor your sales KPIs, measure performance, and stay accountable to your daily activity.Join the LinkedIn Prospecting Course to improve how you use LinkedIn and book more consistent, high-quality sales appointments.Visit <a...

Sales enablement is meant to make selling easier, yet many teams struggle to see real results from it. In this rerun episode, Ahmad Munawar breaks down why most sales enablement efforts fall short and what leaders must do to turn enablement into a true revenue driver. We explore alignment, execution, and how enablement should support sellers in real conversations, not just live in documents and dashboards.Why Sales Enablement Misses the Mark (00:02:12 – 00:03:45)Ahmad explains that sales enablement often becomes content-heavy but action-light.Teams create playbooks, tools, and training without tying them directly to how sellers actually sell.Enablement fails when it is disconnected from daily selling behavior.The Gap Between Strategy and Execution (00:03:45 – 00:05:30)Many organizations design enablement strategies in isolation.Ahmad highlights how lack of alignment between leadership, marketing, and sales creates confusion and inconsistent execution in the field. Alignment is what turns strategy into results.What Sellers Actually Need From Enablement (00:05:30 – 00:07:15)Enablement should help sellers:Start better conversationsHandle objections confidentlyMove deals forward fasterAhmad emphasizes that practical guidance always beats theoretical frameworks.Why Content Alone Does Not Change Behavior (00:07:15 – 00:08:55)Simply giving sellers more content does not improve performance.Ahmad explains that enablement must reinforce skills through repetition, coaching, and real-world application.Behavior change requires reinforcement, not information overload.Measuring Enablement Impact the Right Way (00:08:55 – 00:10:35)Instead of tracking content usage alone, Ahmad encourages teams to measure:Conversation qualityDeal progressionRep confidence and consistencyEnablement success should be visible in pipeline movement and close rates.How Leaders Can Support Enablement Adoption (00:10:35 – 00:12:20)Leadership buy-in is critical.Ahmad shares how managers play a key role by reinforcing enablement in one-on-ones, pipeline reviews, and coaching sessions.What leaders reinforce is what sellers...

Sometimes all you need is the right personality to close a deal. When you hold back, play it safe, or fail to fully show up, prospects notice and engagement suffers. In this episode, my guest Kevin Hubschmann shares why suppressing your personality can cost you in the long run and how using comedian techniques can help you close a six-figure deal.Blending Humor and Professionalism in Sales·&nbsp;&nbsp;Kevin shares how he balanced his life as a standup comic and improv performer with his full-time sales role.&nbsp;·&nbsp;&nbsp;Like many reps, he struggled to merge his personality with his professional image. Once he stopped separating the two, he began building stronger connections and seeing better outcomes.The Six-Figure Meme·&nbsp;&nbsp;Kevin walks through the real story behind a six-figure deal that started with personality.·&nbsp;&nbsp;After sending nine standard, scripted emails with no response, he tried something different.&nbsp;·&nbsp;&nbsp;His tenth message included a relatable meme, and it finally got a reply. That moment highlights why being yourself and taking smart risks can cut through the noise.&nbsp;·&nbsp;&nbsp;Humor and authenticity help humanize sales and open conversations that traditional outreach often misses.Improv, Listening, and Leadership Support·&nbsp;&nbsp;We talk about how humor in sales is not about telling jokes. It is about listening, reading the room, and responding with empathy.&nbsp;·&nbsp;&nbsp;Kevin shares improv-based techniques like “yes, and,” listening exercises, and reframing ideas to create more engaging conversations and build trust with prospects.·&nbsp;&nbsp;We also discuss the role leadership plays in this process. Sales teams perform better when managers create a culture where reps feel safe showing their personality, trying new approaches, and learning from mistakes.Key Takeaway·&nbsp;&nbsp;&nbsp;Sales is about real human connection. When you combine your personality with professionalism, focus on active listening, and allow room for creativity, better conversations follow. Those conversations lead to stronger relationships and long-term success.“Be yourself, because yourself is what's going to get you loose. It's going to create new ideas. You're going to take more risks..." - Kevin Hubschmann&nbsp;ResourcesDo you want to learn more about Kevin’s laughing and development classes? Check out laugh.events and join his newsletter Laugh Rx Laugh Events.&nbsp;Join my Sales Mastermind to get real-world feedback, accountability, and proven sales strategies. Visit Blue Mango Studios for help in creating podcast production content.&nbsp;Sponsorship Offers1.&nbsp;&nbsp; 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.2.&nbsp;&nbsp;&nbsp;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 <a href="https://business.linkedin.com/sales-solutions/cx/20/09/sales-navigator-podcast?src=re-pod&amp;trk=tse&amp;veh=tse&amp;mcid=6897323946090332160"...

Most deals do not fall apart because prospects say no. They stall because momentum quietly disappears. In this episode, Donald C. Kelly breaks down why sales conversations often lose traction after a strong first call and what sellers must do to keep prospects engaged, aligned, and moving forward. We explore how clarity, commitment, and intentional follow-up prevent ghosting and stalled pipelines.Why Deals Lose Momentum After a Good First Call (00:02:18 – 00:03:45)Donald explains that many salespeople mistake a positive conversation for real commitment.Without clear next steps and buyer ownership, interest fades and urgency drops.Good conversations alone do not close deals. Structured momentum does.The Hidden Cost of Vague Next Steps (00:03:45 – 00:05:25)When follow-ups sound like “I’ll check back in,” prospects disengage.Donald highlights how ambiguity creates uncertainty and gives buyers permission to deprioritize the deal.Clarity builds confidence. Vagueness creates delay.How to Lock in Commitment During the Call (00:05:25 – 00:07:10)Donald shares how to confirm alignment before ending the conversation by summarizing:The problemThe desired outcomeThe agreed-upon next stepWhen prospects verbally agree, follow-through increases.Why Follow-Ups Fail (and How to Fix Them) (00:07:10 – 00:08:55)Most follow-ups fail because they add no value.Donald explains how each touchpoint should reinforce relevance, urgency, or insight instead of simply asking for time.Follow-ups should advance decisions, not chase them.Creating Mutual Accountability With Prospects (00:08:55 – 00:10:40)Deals move faster when both sides share responsibility.Donald discusses how setting expectations, timelines, and roles turns the process into a partnership rather than a pursuit.Mutual accountability reduces ghosting.How to Handle Prospects Who Go Silent (00:10:40 – 00:12:25)Instead of repeated check-ins, Donald recommends reframing silence as feedback.He shares how to re-engage prospects with clarity, honesty, and permission-based messaging.Desperation pushes buyers away. Confidence brings them back.Key Lesson: Momentum Is Created, Not Hoped For (00:12:25 – 00:14:05)Sales success is not about luck or persistence. It is about intentional process.When sellers guide prospects with structure and clarity, deals move forward naturally.“If there’s no clear next step, the deal is already slipping away.” – Donald C. KellyResourcesConnect with Jennifer on LinkedIn and check out scribe.com.Join my Sales Mastermind to get real-world feedback, accountability, and proven sales strategies.Visit Blue Mango Studios for help in creating podcast production content.Sponsorship OffersThis episode is brought to you in part by Hubspot.With HubSpot sales hubs, your data tools...

You can always expect challenges to arise when training a sales team, and when they do, things can go south quickly. Some reps simply don’t ramp as fast as others.How can you ramp your team in half the time? Let’s revisit episode 1610 with Jennifer Smith, co-founder and CEO of Scribe, to find out.Scale YourselfScaling yourself is about identifying the core things you are good at and spending as much time on them as possible. Take the other tasks that fill your time and reduce them, automate them, or delegate them.Jennifer challenges you to track how many interruptions you have and how much time you spend on various tasks during an average day. Those minutes add up.Get People The Things They NeedGet the right information to the right people at the right time so they can use their time effectively.Scale Your Best RepHave your best reps, the people who have been there the longest and know what they are doing, record how they do what they do.Share this information with the rest of your reps so that they can learn from the information and knowledge that makes your best rep really good.If all the reps are able to share with each other what is working, everyone will learn together to create a rapid learning machine.“If you’re doing anything that doesn’t involve talking to a customer, ask yourself: could I scale this?” — Jennifer SmithResourcesConnect with Jennifer on LinkedIn and check out scribe.com.Join my Sales Mastermind to get real-world feedback, accountability, and proven sales strategies.Visit Blue Mango Studios for help in 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 <a...

Relying on outdated selling methods will have buyers viewing you like a sleazy car salesperson. Today, how you sell matters more than ever. I’m revisiting episode 1533 with Andy Paul to remind you why having a human approach to selling matters. He shares how you can sell effectively without selling out.Great Selling Isn’t One-Size-Fits-AllThe push toward sales conformity is really for management, not the seller, because management wants predictability. However, the real world is more complicated.You learn, take those lessons, and apply them to life. You become the sum of your experience and knowledge. We all end up doing things differently, even if those approaches lead to the same result.Despite all the tools and technological advancements that benefit us, we aren’t getting better at selling. We have ready access to a world of information, creating a better and more efficient buying experience. However, our win rates are dropping.Where Seller Education Goes WrongWhen asked, “What’s your job?” the answer often comes back, “To persuade someone to buy my product.”In reality, your job is to listen to the prospective buyer’s challenges and help them find resources to overcome those problems.Just because you can do something doesn’t mean you should.The Catalyst by Jonah Berger explains that human beings resist being persuaded.Instead of persuasion, think about it from an influential perspective. Persuasion is coercive, while influence affects others without force. It’s a change in mindset.Four Pillars of Changing SalesConnection: Some people conflate a relationship with friendship. While you don’t need to be friends with buyers, you do make connections in every interaction you have.Curiosity: We understand the world through curiosity and asking questions. The commonly accepted sales process allows very little time for discovery, but in reality, discovery should happen in every conversation with a prospect or buyer.Understanding: Your job is to listen to the buyer. What’s the context? A salesperson’s effort to understand the buyer is an ongoing process that should never stop. Fully understanding the buyer allows you to determine how you can help them overcome challenges.Generosity: Humans are wired to give and collectively support one another. Generosity triggers reciprocity, and its purpose is to achieve what is essential for both parties.“Value exists only in the eyes of the buyer. Every interaction you have with a buyer should bring them closer to making a decision.” - Andy Paul.ResourcesVisit Andy’s website to learn more about him and order a copy of his book. You can also learn more about <a href="https://www.linkedin.com/in/realandypaul/" rel="noopener noreferrer"...

Is it still possible to reach seven figures in SaaS sales? You got into sales to build a comfortable life and enjoy a little extra. But after how last year turned out, that goal may feel far-fetched.To help you reset and refocus, I’m revisiting episode 1528 with Brandon Fluharty, sales coach and founder of Be Focused. Brandon breaks down his seven steps to start making seven figures in SaaS sales, starting with one critical shift in mindset.1. Get In The Right Environment· Find your Goldilocks situation concerning your ideal workplace, whatever that may be.· What kind of internal infrastructure do you need to start making seven figures in SaaS? 2. Build A Transformation Mindset· Seven-figure earners sell a transformation that doesn’t just solve an issue; it prevents the problem from happening again.· In SaaS, you want to be the player touching multiple parts of the business. That requires a transformational mindset and is a key principle of Brandon’s framework.3. Be Strategic About Your Target Account List· Sell to clients that give you purpose. Identify the reasons you prefer your ideal client and search for more that fit those criteria.· Doing so keeps you motivated during the dishearteningly long sales cycles common with enterprise companies.4. Create A Standard No One Else Delivers· The Diamond Standard: picture a coal field in your competitive landscape and be the diamond for your clients.· It’s easier to perform to this standard when working with clients you’re genuinely interested in and passionate about.5. Break Through Personal Limitations· The higher you climb, the more imposter syndrome you’ll feel. For example, Brandon initially thought his introversion limited his success.· As he advanced, he realized he could listen more than he talked and that perceived weakness became a strength.· Write down the traits you feel hold you back. Then ask yourself how you can repurpose them into strengths.6. Rally Others Inside Your Organization· Nothing great is achieved alone. When you’re working toward seven- and eight-figure deals, you’ll need help.· Be a generalist with your skill set, but a specialist to start making seven figures in SaaS.7. Develop A Personal Operating System· Move away from hustle culture and work smarter.· Balance Brandon’s Discipline, Flexibility, and Curiosity (DRC) and Plan, Rest, Effort, Performance (PREP) live life instead of hustling around the clock. (It’s a more humanistic approach.)“Be like a scientist and look back at your workday with curiosity.” — Brandon Fluharty.ResourcesFollow Brandon Fluharty on LinkedIn and subscribe to his bi-weekly newsletter for more content, information, and insights on tech sales. Join my Sales Mastermind to get real-world feedback, accountability, and proven sales strategies.Visit Blue Mango Studios for help in creating podcast production content. Sponsorship Offers1. 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 <a href="https://www.hubspot.com/products/sales" rel="noopener noreferrer"...

Most sales outreach blends into the noise not because sellers lack effort, but because they approach prospects the same way everyone else does. In this episode, Ashley Winston breaks down why traditional outreach tactics fall flat and how sales professionals can stand out by leading with relevance, clarity, and genuine curiosity. We explore how to create conversations that feel natural, human, and worth responding to.Why Prospects Ignore Most Sales Outreach (00:02:10 – 00:03:35)Ashley explains that buyers aren’t ignoring messages because they’re rude, they’re overwhelmed.Generic outreach, vague value statements, and self-focused messaging give prospects no reason to engage.The real issue isn’t volume, it’s relevance.The Biggest Mistake Salespeople Make in Messaging (00:03:35 – 00:05:10)Most outreach talks about the seller instead of the buyer.Ashley shares why messaging that leads with credentials, features, or company history immediately creates disengagement.Prospects care less about who you are and more about whether you understand them.How to Personalize Without Overcomplicating It (00:05:10 – 00:06:55)Personalization doesn’t mean writing long messages.Ashley explains how small signals like role relevance, timing, and context, dramatically increase response rates without extra effort.Relevance beats creativity every time.Using Curiosity Instead of Pressure (00:06:55 – 00:08:30)Rather than pushing meetings, Ashley encourages sellers to spark curiosity.Open-ended questions invite conversation and reduce resistance, making prospects feel in control instead of sold to.Pressure ends conversations. Curiosity starts them.How to Earn Replies Without Chasing Prospects (00:08:30 – 00:10:05)Ashley breaks down why follow-ups fail when there’s no value added.Each touchpoint should introduce a new insight, observation, or reason to respond not just “checking in.”Silence is feedback. Adjust accordingly.What High-Performing Sellers Do Differently (00:10:05 – 00:12:10)Top performers focus on quality conversations, not activity metrics.Ashley explains how intentional outreach, patience, and consistency lead to better pipeline health and stronger relationships.Selling is about connection, not coercion.Key Lesson: Make It About Them, Not You (00:12:10 – 00:13:55)When outreach is centered on the buyer’s world, challenges, and priorities, responses come naturally.Sales success comes from empathy, relevance, and respect, not persistence alone.“If your message doesn’t immediately answer ‘Why should I care?’, it won’t get a reply.” – Ashley WinstonResourcesWant help applying these strategies directly to your pipeline and hitting your quota?Join The Sales Evangelist Mastermind, a 90-day program designed to help you close more deals and hit your number.Learn more at thesalesevangelist.com/mastermindSponsorship OffersThis episode is brought to you in part by HubSpot.With HubSpot Sales Hub, your data, tools, and teams come together on one platform to help you close deals faster. Try it at hubspot.com/sales.This episode is brought to you in part by LinkedIn.Tired of prospects not responding? Get 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 LinkedIn outreach and land 3–5 appointments with our LinkedIn Prospecting Course.Visit <a href="http://thesalesevangelist.com/linkedin" rel="noopener noreferrer"...