The Sales Evangelist

Latest Episodes:

LinkedIn: Once You've Connected With a Prospect, Here's What You Should Do Next | Ahmad Munawar - 1968 Jan 16, 2026

Show notes

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 conversations
Handle objections confidently
Move deals forward faster
Ahmad 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 quality
Deal progression
Rep confidence and consistency
Enablement 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 adopt.

Key Lesson: Enablement Must Serve the Seller, Not the System (00:12:20 – 00:14:05)

Sales enablement works when it is built around how buyers buy and how sellers sell.
When enablement supports real conversations and real challenges, revenue follows.

“If enablement does not help a seller win the next conversation, it is not doing its job.” – Ahmad Munawar

Resources

Learn more about modern sales enablement and revenue alignment at: thesalesevangelist.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.

Here is how I closed a 6-figure deal with humor | Kevin Hubschmann - 1967 Jan 12, 2026

Show notes

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

· Kevin shares how he balanced his life as a standup comic and improv performer with his full-time sales role.

· 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

· Kevin walks through the real story behind a six-figure deal that started with personality.

· After sending nine standard, scripted emails with no response, he tried something different.

· 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.

· Humor and authenticity help humanize sales and open conversations that traditional outreach often misses.

Improv, Listening, and Leadership Support

· We talk about how humor in sales is not about telling jokes. It is about listening, reading the room, and responding with empathy.

· Kevin shares improv-based techniques like “yes, and,” listening exercises, and reframing ideas to create more engaging conversations and build trust with prospects.

· 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

· 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

Resources

Do you want to learn more about Kevin’s laughing and development classes? Check out laugh.events and join his newsletter Laugh Rx Laugh Events.

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 Offers

1. 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. 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.

3. 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

8 Sales Predictions for 2026 | Donald C. Kelly - 1966 Jan 09, 2026

Show notes

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 problem
The desired outcome
The agreed-upon next step
When 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. Kelly

Resources

Connect 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 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

3 Ways to Train and Ramp Your Team in Half the Time | Jennifer Smith - 1965 Jan 05, 2026

Show notes

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 Yourself

Scaling 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 Need

Get the right information to the right people at the right time so they can use their time effectively.

Scale Your Best Rep

Have 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 Smith

Resources

Connect 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 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

Sell Without Selling Out | Andy Paul - 1964 Jan 02, 2026

Show notes

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-All

The 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 Wrong

When 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 Sales

Connection: 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.

Resources

Visit Andy’s website to learn more about him and order a copy of his book. You can also learn more about him on LinkedIn.

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 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

7 Steps to Making 7 Figures in Enterprise SaaS Sales | Brandon Fluharty - 1963 Dec 29, 2025

Show notes

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.

Resources

Follow 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 Offers

1. 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. 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.

3. 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

How to Unlock Your Earning Potential This Year | Ashley Winston - 1962 Dec 26, 2025

Show notes

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 Winston

Resources

Want 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/mastermind

Sponsorship Offers

This 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 thesalesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your feedback and want to keep improving the show.

Complete our two-minute survey at thesalesevangelist.com/survey.

Join us for future episodes on Apple Podcasts, Google Podcasts, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Music credits include The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Bright Seed and Hill.

How Properly Conduct a Discovery Call & Not Scare Away Your Prospect | Jeremy Miner - 1961 Dec 22, 2025

Show notes

Traditional selling pushes prospects away. In this episode, Jeremy Miner breaks down why old-school persuasion no longer works and how modern buyers respond to questions that help them uncover their own problems and motivations. We explore how to reduce resistance, increase trust, and guide prospects to decisions without pressure by using a question-based, psychology-driven approach.

Why Prospects Resist Being Sold (00:02:14 – 00:03:40)

Jeremy explains that buyers are more informed than ever and can sense manipulation instantly. When salespeople push solutions too early, prospects naturally defend themselves by shutting down or disengaging. The key problem isn’t price or timing, it’s resistance created by the sales approach.

Why Features and Pitches Kill Momentum (00:03:40 – 00:05:22)

Most sales conversations fail because sellers talk too much about themselves. Jeremy shares why feature-dumping and early pitching overwhelm buyers and prevent emotional engagement. People don’t buy when they’re told, they buy when they discover.

How Question-Based Selling Reduces Pressure (00:05:22 – 00:07:10)

Instead of convincing, Jeremy teaches how to guide prospects with thoughtful, problem-aware questions. The goal is to help buyers verbalize:

Their challenges

The consequences of not changing The urgency to act When prospects say it themselves, belief and commitment increase.

Helping Prospects Connect Emotion to Problems (00:07:10 – 00:08:55)

Logical reasons start conversations, but emotional reasons close deals. Jeremy explains how to ask questions that uncover frustration, fear, or missed opportunity without sounding manipulative. Emotion creates urgency; logic justifies the decision.

How to Talk About Solutions Without Sounding Salesy (00:08:55 – 00:10:30)

Jeremy emphasizes delaying solution talk until the prospect fully understands their own problem. When solutions are positioned as answers to their words, not your pitch, resistance disappears. Timing matters more than wording.

Preventing Ghosting by Creating Commitment (00:10:30 – 00:12:05)

Ghosting happens when prospects aren’t emotionally invested. Jeremy explains how confirming commitment throughout the conversation instead of at the end, keeps deals moving forward. If there’s no internal urgency, follow-ups won’t matter.

The Role of Neutrality in Closing More Deals (00:12:05 – 00:13:55)

One of the most powerful ideas Jeremy shares is remaining neutral. When sellers stop needing the deal, prospects feel safer opening up and making honest decisions. Confidence comes from control not pressure.

Key Lesson: Stop Convincing, Start Guiding (00:13:55 – 00:15:30)

The biggest shift modern sellers must make is moving from persuasion to facilitation. When prospects feel understood instead of sold to, decisions happen faster and with less resistance.

“The moment you stop trying to convince someone is the moment they start convincing themselves.” Jeremy Miner

Resources

Learn more about Jeremy Miner and his question-based selling framework at: 7thlevelhq.com

Explore training on modern selling psychology and objection-free conversations.

Want 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/mastermind

Sponsorship Offers

This 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 thesalesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your feedback and want to keep improving the show.

Complete our two-minute survey at thesalesevangelist.com/survey.

You’re Closing Too Late, Here’s How to Fix It! | Benjamin Dennehy - 1960 Dec 19, 2025

Show notes

You have a discovery call with a prospect, and they seem interested in your product—until it's time to follow up. After three attempts, you finally get the message: you waited too long to close the deal.

What can you do differently to prevent this from happening again? Listen to my chat with Benjamin Dennehy, who explains why sellers often get stuck in a "matrix" and how it prevents them from closing deals at the right time.

Meet Benjamin Dennehy

· Meet Benjamin Dennehy, known as the UK’s most hated salesperson, all thanks to his amazing marketing campaign.

· He shares how sellers often make the mistake of closing when prospective buyers are expecting them to.

· Don’t forget that you’re the one with all the power when it comes to choosing the right time to close a deal.

The Sales Matrix: Closing At The Wrong Place

· When first starting in the industry, Benjamin discovered that most sellers live in a system they don’t realize they’re part of. This is another reason why sellers tend to close deals at the wrong time.

· There are also two systems when sellers are out in the field: the buyer's system and the seller’s system. The problem arises when these two systems intertwine, making the buyer appear as the winner.

· Due to conditioning, buyers are aware that if they say no to a seller, the seller won't stop. So, they think of other ways to try to keep sellers from continuing without actually saying no.

· Benjamin delves into the list of reasons why prospective buyers give objections or deceive sellers to prevent a deal from moving forward. I'm sure you’ve heard plenty of these!

· He also explains how the matrix is designed to prevent sellers from exerting control in closing deals, and how their buying habits lead them to sympathize with prospective buyers when they express their objections.

How to Get Out of the Sales Matrix

· To get out of the sales matrix, Benjamin shares that sellers must start closing at the beginning of the first meeting. When you try to close at the end, you give the buyer complete control over what happens next.

· At the start of the meeting, Benjamin does three things to get a prospect to say no:

o Get permission from them to say no. If they believe the product is of no use, then there's no point in continuing the conversation. This will also let you know if the person you're speaking to is the decision-maker.

o When speaking with the CEO, he asks a series of questions to determine if he can actually assist their company with their problem. If there's no "no" in these answers, then he moves on to the third step.

o This is when he'll discuss how they can move forward together to close a deal.

· The method works because if prospects aren't logically saying no, then they have to agree to move forward.

“We've been told a lie that the person with all the money has the power. But in reality, money only has power when someone wants it.” - Benjamin Dennehy.

Resources

Follow Benjamin on LinkedIn, YouTube, and Instagram.

Don't forget to DM the code TSE for a link to his two free courses.

You can also learn more about him on his website.

Sponsorship Offers

1. 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. 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.

3. 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

Three Reasons Most Enterprise Deals Stall | Donald C. Kelly - 1959 Dec 15, 2025

Show notes

In this episode of the Sales Evangelist podcast, Donald C. Kelly reveals the top three reasons why enterprise deals stall, offering listeners practical solutions to overcome these hurdles. Whether you're new to enterprise sales or struggling to close deals, this episode is packed with actionable insights that can elevate your sales game.

Misalignment Within the Buying Committee

● Understand that decisions in enterprise sales are often made by committees, leading to internal misalignment among stakeholders.

● Use a mutual action plan to align all committee members, ensuring everyone is on the same page and clear about the project's importance.

● Leverage tools like digital sales rooms to facilitate communication and provide access to demos and materials for all committee members.

Perceived Risk and its Impact

● High perceived risk can paralyze decision-makers; ensure to highlight previous successes with similar organizations to reduce apprehension.

● Customize demos to reflect the prospect's unique environment, showcasing specific processes to minimize perceived risk and create relevance.

Providing Clear Value

● Focus on the most impactful features that resonate with each committee member to highlight your solution’s value effectively.

● Use stories, testimonials, and case studies to reinforce the solution’s benefits and drive home its ROI, ensuring buyers see the potential for personalization and growth.

Homework Challenge or Action Steps

● Create a mutual action plan for your next enterprise deal to foster committee alignment.

● Focus on understanding each committee member's individual goals and challenges related to the project.

"Don't sell on everything—sell on the thing that matters the most." ● Donald C. Kelly.

Timestamps

● 00:00 ● Introduction

● 01:20 ● Misalignment Within the Buying Committee

● 03:44 ● Perceived Risk and its Impact

● 08:32 ● Providing Clear Value

● 10:58 ● Closing thoughts

Resources

● Sales Evangelist Mastermind: [Join Here](https://thesalesevangelist.com/mastermind)

● Mutual Action Plan Guide: [Learn More](https://www.mutualactionplan.com)

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

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2. This episode is brought to you in part by LinkedIn.

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3. This episode is brought to you in part by the TSE Sales Foundation.

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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.

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