The Sales Evangelist

Don’t dream small as a seller. Always think bigger than what feels comfortable. My guest, Jason VanDevere, author of the bestselling book Dream Driven and founder of the Goal Crazy platform, shares an incredible story about his car dealership business and how a 90-day plan can completely shift results. He also breaks down five principles that challenge you to remove limitations and start moving toward bigger goals with intention.

Meet Jason VanDevere

• Jason VanDevere is the author of the bestselling book Dream Driven and the founder of the Goal Crazy platform, which helps entrepreneurs set goals, manage their time, and actually follow through on what matters most.
• After leaving his family’s successful car dealership business, Jason went on to build a multi-million dollar real estate portfolio and create the Goal Crazy Planner, now used by tens of thousands of people to stay focused and hit their goals.
• He lives in Akron, Ohio with his wife and four children, and also shares insights as the host of the Goal Crazy Podcast.

The Power and Process of Dreaming Without Limits

• How do you know which dreams actually matter? Jason shares that when he left his family’s successful car dealership, many people saw it as a mistake. But he trusted his system and his vision enough to move forward anyway.
• For him, dreams are the space where your heart gets to express what it really wants without limitations. Goals are more structured and specific, but when your goals are connected to your deeper dreams, they carry real meaning and purpose.

Why Do We Limit Our Dreams

• Most people don’t struggle with goals, they struggle with dreaming.
• We spend so much time focused on bills, responsibilities, and staying afloat that we slowly shrink what we believe is possible. Survival mode becomes the default.
• That’s why Jason intentionally creates space for dreaming. He’ll turn on music, step away from distractions, and spend about ten minutes visualizing the life he actually wants to build.

Setting Breakthrough Goals That Stretch You

• After getting clear on your long-term dreams, the next step is choosing a yearly goal that currently feels slightly out of reach. Not impossible, but uncomfortable enough that it requires you to level up.
• The goal should be exciting, but also demanding. It should push you to learn new skills, face fears, and step outside what feels familiar.
• Jason draws from Tony Robbins’ philosophy here, emphasizing that the real value is not just hitting the goal, but becoming the person who is capable of achieving it.
• If it already feels easy or fully within reach, it is not a breakthrough goal. It is just another task on a checklist.
• The purpose of this approach is growth. You are constantly stretching, evolving, and aligning your actions with a bigger vision of what you are capable of becoming.

“A problem with goal setting is that many people skip the dreaming step. You can still set goals without dreams, but they lack direction and meaning. Without that, people end up in survival mode, just working to stay afloat. When goals are tied to real dreams, they become meaningful and bring purpose back into your life.” — Jason VanDevere

Resources

• Connect with Jason VanDevere on LinkedIn and visit GoalCrazy.com to explore his planners, resources, and coaching opportunities.
• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

We’re tapping into a Renaissance era in sales. AI is changing how sellers operate, but human connection is still what builds trust and closes deals. My guest, Yiannis Gavrielides, Co-founder and CEO of Covve, shares how trade shows remain one of the strongest ways to build real relationships in a digital-first world.

Meet Yiannis Gavrielides

• Yiannis Gavrielides is the co-founder and CEO of Covve, a lead capture and relationship intelligence platform helping sales teams and professionals turn every meeting into a real pipeline.
• Covve is used by over 2 million people across 130+ countries, from solo founders to global companies like Delta and Prudential.
• A serial founder across technology, media, and hospitality, Yiannis built Covve on one core belief: in an AI-first world where emails, decks, and even calls can be automated, trust is still the one thing technology cannot replace.
• Before Covve, he worked in consulting and banking in London. Today, he focuses on helping sales teams turn human connection into their most defensible competitive advantage.

Basics of Building Trust in Sales

• We’re living in an era where everything is being automated, from emails to scheduling to large parts of the sales process.
• But even in a digital-first world, very few people can walk into a room and naturally connect with everyone by the end of an event. Shout out to my good friend Jared for being able to do this.
• Connection is everything in sales. Instead of focusing on selling right away, the real shift is learning how to stay curious about people.
• Yiannis shares insights from anthropologist Professor Robin Dunbar. When we meet someone new, we immediately start looking for shared signals.
• Things like accent, humor, interests, or communication style. These small cues help us decide, often subconsciously, whether a connection is forming. That first layer of recognition is what builds trust.

Re-Booking Meetings for Success

• Successful trade show follow-up starts before the event even happens. The key is identifying the right people you want to meet and setting meetings in advance whenever possible.
• Use LinkedIn and AI tools to research key attendees so you can connect over shared industry insights instead of leading with a sales pitch.
• The goal is simple. Build relationships first, and let business conversations follow naturally.

Finding the Right Trade Shows & Preparation

• Start by clearly defining your ideal customer profile so you know exactly who you are targeting, including companies, roles, and regions.
• From there, use tools like 10times and Evensi, along with AI, to research and organize trade shows. This helps you evaluate events based on timing, size, and relevance to your audience.
• Bigger is not always better. The most effective events are the ones where your ideal buyers are actually present in meaningful numbers.
• The real advantage comes from preparation. The most successful sellers are already identifying attendees and starting conversations before they ever arrive at the show.

“When we show up as human and treat the other person like a human being with curiosity and genuine interest, we start finding what we have in common. That’s what builds trust, and that trust can then grow into something more meaningful and useful.” — Yiannis Gavrielides

Resources

• Get 20% off Covve business plans with code TSE26
• The Networker: free newsletter and podcast on relationship building
• Connect with Yiannis Gavrielides on LinkedIn.
• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

In the final part of this customer success and retention series, I share how businesses can move beyond simple transactions and turn satisfied customers into true brand evangelists. The focus is on creating experiences that people remember and naturally want to talk about.

The Power of Memorable Experiences

• Brand evangelists are not created by accident. They are built through intentional experiences that feel thoughtful and immersive.
• Some of the best examples of this come from companies like Disney, where every detail is designed to fully immerse guests in the experience.
• Chick-fil-A, where every interaction is grounded in gratitude and positivity. And the Ritz Carlton, where employees are empowered to solve problems quickly and go above and beyond for guests.

Small Gestures, Big Impact

• You do not need massive systems to create loyal customers. Often, it is the small things that make the biggest difference.
• Simple actions like handwritten notes, birthday messages, or personalized videos can go a long way. Taking time to actively listen and truly acknowledge customers also helps them feel seen and valued.
• Even recognizing milestones like one-year anniversaries or highlighting loyal customers can strengthen the relationship.

The Four Levels of Buying

• Customers typically move through four stages in their relationship with a brand.
• It starts with a buyer, then a repeat buyer, followed by a loyal customer. The highest level is an evangelist, someone who not only stays with your brand but actively refers others and speaks positively about your business in places like podcasts, social media, and conversations.

“Usually it's not taking a huge fix to be able to switch and get people to become evangelists. It's just the little things. And I can tell you those little things are what make a difference.” - Donald C. Kelly.

Resources

• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

It costs 5x more to attract new customers than to retain existing ones, which is why client retention matters so much. For part two of this series, I am going over the five pillars of customer success.

Pillar 1: Exceptional Onboarding

• Strong customer success starts the moment a client says yes. Onboarding should feel seamless, intentional, and personal, using things like welcome emails, videos, and thoughtful check-ins to make customers feel valued right away.
• This stage is also where buyer’s remorse can show up, so a strong onboarding process helps reinforce that they made the right decision. Even small personal touches like a handwritten note or a public shout-out can create a deeper connection early on.

Pillar 2: Consistent Communication

• Retention depends heavily on staying visible. Customers should not feel forgotten after the sale, which is why consistent communication matters.
• This can be done through newsletters, social media updates, or ongoing educational content that helps them get more value from what they purchased. Over time, this kind of communication builds familiarity and creates a sense of belonging with your brand.

Pillar 3: Deliver Unexpected Value

• One of the most powerful retention tools is giving customers more than they expect. Small, thoughtful gestures can leave a lasting impression and strengthen loyalty.
• This might look like surprise gifts, unexpected discounts, or sharing insights that would normally be behind a paywall. Exclusive content, private access, or special events can also make customers feel like they are part of something unique.

Pillar 4: Focus on Customer Success

• Customer success is not just about satisfaction. It is about results.
• Instead of simply asking if customers are happy, the focus should be on whether they are actually achieving their goals. When they are struggling, it becomes the responsibility of the business to step in with guidance, support, and hands-on help to get them back on track.

Pillar 5: Referral and Advocacy System

• Many customers are willing to give referrals, but very few businesses actually ask for them in a structured way.
• Building a system around referrals means making it easy, natural, and consistent. This includes asking at the right moments, encouraging testimonials, and recognizing customers who refer others. Over time, this turns satisfied customers into active advocates for your brand.

“91% of customers say they would be willing to give a referral, but only 11% of salespeople actually ask. That gap represents a major misalignment in the sales process.” — Donald C. Kelly

Resources

• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

Retention of a client will take you much further than constantly being on the hunt for a new one. I’m sharing a three-part series on client retention for sellers who struggle with keeping clients for the long term. This first part focuses on how to move away from the “leaky bucket” approach and start using strategies that actually help you retain and grow your customer base.

Why Customers Leave

• Many people assume customers leave because of price or missing features, but it often goes much deeper than that.
• A big reason customers walk away is because they feel forgotten after the initial sale. The relationship starts strong, but once the “honeymoon phase” is over, communication drops off.
• Others leave because they stop seeing ongoing value. If they no longer feel like they are getting something meaningful from the relationship, their interest fades over time.
• Inconsistency also plays a major role. When service starts strong but becomes unreliable, trust breaks down quickly.
• And sometimes, it is as simple as attention. If a competitor is showing up more consistently and staying top of mind, customers will naturally drift in that direction.

Shifting to a Lifetime Value Mindset

• To improve retention, sellers need to move away from a one-time transaction mindset and focus more on Customer Lifetime Value.
• Instead of thinking about a single sale, it is about what that relationship can grow into over time. A small purchase can turn into long-term value when trust and consistency are built into the relationship.
• The key shift is learning to see customers as ongoing relationships, not one-time transactions.

Strategies for Success

• Strong retention comes from staying present and intentional.
• One approach is using tools like LinkedIn Sales Navigator to keep track of customers, note changes in their careers or life events, and use those moments as natural ways to reconnect.
• Another is staying proactive instead of reactive. That can look like weekly tips, helpful content, or even simple handwritten notes that remind customers they are still valued beyond the initial sale.
• At the core, retention comes down to consistency, attention, and showing up even when nothing is wrong.

“It’s cheaper to keep a current customer than get a new one.” - Donald C. Kelly

Resources

• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

So many sellers quit within their first few months in sales. Honestly, I think many of them give up too soon.

Sales isn't easy, but success often comes down to staying committed when things aren't going your way. I'm sharing why determination matters, how to push through rejection, and why the sellers who keep going are often the ones who eventually succeed.

Why Determination Matters in Sales

• Early in my college years, I found myself stranded in California with a friend during a business trip.
• We had no transportation, limited options, and needed to get back to our hotel. Instead of giving up, we stayed focused on finding a solution. Because we were determined to make it back, we noticed opportunities that we might have otherwise overlooked.
• That experience reinforced a lesson I've carried with me ever since: when your reason for succeeding is strong enough, you'll find a way through obstacles that might stop other people.

Stop Letting Fear Hold You Back

• One challenge many sales professionals face is the fear of rejection. Too often, sellers hesitate to follow up because they worry about being annoying or reaching out too many times.
• But if you genuinely believe your solution can help someone solve an important problem, then it's your responsibility to start the conversation.
• Most buyers won't remember how many times you called or emailed. They'll remember the value you helped them create.

Use AI to Prospect Smarter

• Persistence is important, but that doesn't mean wasting time on the wrong opportunities.
• Today's sellers have access to AI tools that can help identify companies experiencing specific challenges and uncover prospects who are more likely to engage.
• Instead of blasting generic messages to thousands of people, you can narrow your focus and spend time with the accounts that matter most.
• The goal is simple: become more relevant and intentional with your outreach.

Take a Multi-Channel Approach

• Prospecting works best when you meet buyers where they are. That's why I encourage sellers to combine phone calls, emails, and LinkedIn outreach.
• Some prospects may respond to email, while others prefer social engagement or a direct conversation. Using multiple channels increases your chances of reaching the right decision-maker at the right time.

Get Back to the Fundamentals

• At the end of the day, sales success still comes down to the basics.
• Believe in your solution. Build a targeted list. Stay focused on the people you can help. Most importantly, remain relentless when obstacles appear.
• The sellers who succeed are often the ones who keep moving forward long after everyone else has decided to quit.

“If you have a reason strong enough, no obstacle can stop you.” - Donald C. Kelly

Resources

• Ready to transform your prospecting strategy? Check out Episode 1996 to learn a powerful new method for using Claude to achieve a refined focus.
• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

Sales has changed dramatically in the age of AI, but success still comes down to having the right strategy. That's why I sat down with Tom Stearns and Peter Cleary, co-authors of Graphic Sales: How to Build a Prospecting Playbook. They shared how sales teams can move beyond vanity metrics and build a data-driven prospecting process that helps reps focus on the right opportunities and generate better results.

Meet Tom Stearns and Peter Cleary

• Tom Stearns and Peter Cleary are the co-authors of Graphic Sales: How to Build a Prospecting Playbook, a book designed to help sales professionals build more effective prospecting strategies through visual storytelling and practical frameworks.
• Tom is a consultant who has worked with companies across dozens of industries, helping sales teams improve performance through data-driven prospecting. His work focuses on building prospecting playbooks, analyzing sales metrics, and helping organizations identify the behaviors that lead to consistent results.
• Peter previously served as a Director and Senior Director of Engineering. He believes great salespeople focus on solving business problems and that success comes through collaboration and teamwork.
• Together, Tom and Peter combine sales strategy, data analysis, and real-world business experience to help organizations create more focused and effective prospecting processes.

Building a Strong Ideal Customer Profile

• One of the biggest lessons from this discussion is the importance of knowing exactly who you should be selling to.
• The best way to build an Ideal Customer Profile (ICP) is by studying your most successful customers. Look at the clients who stay the longest, get the best results, and genuinely enjoy working with your company.
• From there, you can identify the traits that predict success and use those insights to guide your prospecting efforts.
• We also talked about creating a "hell no list." While many organizations focus on ideal customers, it's just as important to recognize the types of accounts that consistently create challenges, consume resources, or simply aren't a good fit.

Why Every Sales Team Needs a Playbook

• A sales playbook provides structure and consistency for an organization.
• It helps teams document what works, align around proven processes, and create repeatable success. More importantly, a playbook should never be treated as a static document.
• Markets change. Buyers change. Strategies evolve. The most effective sales teams regularly review and update their playbooks to reflect what's happening in the real world.

Become a Student of the Market

• For individual sales reps, one message stood out throughout the conversation: pay attention to the data.
• Successful sellers study their market, analyze which conversations move forward, and look for patterns in their results. They don't abandon a strategy because of a bad week or a few difficult prospects.
• Instead, they remain consistent while gathering enough information to determine whether adjustments are truly needed.

Winning in the Modern Sales Environment

• Sales has always been about helping people solve problems, but today's environment requires a more disciplined approach.
• The sellers who thrive are the ones who combine curiosity, consistency, and data-driven decision-making. When you understand your ideal customer, follow a proven process, and continually learn from the market, you put yourself in a much stronger position to succeed.

"Don't think of it as a project; think of it as a discipline." — Tom Stearns

"If you try to do it alone, you'll probably fail. Sales is a team effort, and success requires a lot of open communication and collaboration." — Peter Cleary

Resources

• Buy the guests' new book, Graphic Sales: How to Build a Prospecting Playbook, which is available globally through online retailers such as Amazon and Barnes & Noble.
• Visit the website stearns.io to read the first chapter of their book for free.
• Reach out to Tom Stearns and Peter Cleary on LinkedIn to stay updated on their latest sales insights.
• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

One of the biggest mistakes sellers make is focusing too quickly on their product instead of understanding the deeper problem their customer is trying to solve.

That’s why I wanted to bring back this conversation with Jeff Koser, founder and CEO of Zebrafy. Even though this episode originally aired during the pandemic, the principles still apply today, especially when it comes to standing out in crowded markets and building trust with buyers.

Why Surface-Level Selling Doesn’t Work

• Jeff explained that too many sales reps stop at surface-level conversations.
• Customers do not buy because your product has more features. They buy because they believe you understand the real business problem they are facing and can help them solve it.
• That requires deeper research, better questions, and understanding the customer’s world before pitching a solution.

The Importance of “Voice of the Customer”

• One idea that really stood out to me was Jeff’s concept of “voice of the customer.”
• Instead of only relying on your company messaging, Jeff encourages sellers to learn directly from customers by understanding:
• the problems customers believe were solved
• the value created after solving those problems
• and the measurable business impact the solution delivered
• That insight helps sellers communicate in a way that feels more relevant and customer-focused.

Why Respectful Outreach Matters

• Jeff also shared why thoughtful outreach matters more than ever.
• Buyers are overwhelmed with emails, automated messaging, and generic pitches. Sellers who take the time to personalize their communication and genuinely understand customer priorities immediately separate themselves from the competition.
• At the end of the day, the best sales conversations happen when customers feel understood, not sold to.

“We have to recognize that what we’re selling may not be everyone’s priority right now, which is why every sales conversation should give people a respectful and simple out.” - Jeff Koser

Resources

• Connect with Jeff Koser’s website to learn more about customer-focused selling strategies, and grab a copy of Voice of the Zebra by Jeff and Chad Koser for additional insights on identifying and reaching your ideal prospects.
• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

Lately, I’ve been hearing more sellers say the same thing: “I’m losing my joy in sales.”

Honestly, I get it. Selling today feels different than it did a few years ago. Cold outreach is harder, inboxes are crowded, buyers are more cautious, and deals take longer to close.

When the wins slow down, it can start feeling like you’re just grinding through the motions instead of enjoying the work. But I truly believe you can get that excitement back.

Start With Your Why

• One of the biggest things that helped me was reconnecting with my purpose.
• At different stages of life, your “why” changes. Early on, mine was helping my family avoid financial struggles we experienced growing up. Today, it’s creating experiences with my wife and kids and building something meaningful through the work I do.
• Your why might be freedom, travel, financial goals, family, or building your own business someday. Whatever it is, you need something bigger than quotas pushing you forward.

Make Sales Fun Again

• Another thing that helps is creating milestones you can work toward.
• Maybe it’s reaching a certain income level, landing a leadership role, joining a startup, or eventually building your own company. When you give yourself goals beyond just surviving the quarter, sales become more exciting again.

The People and Industry Matter Too

• The environment around you matters more than people realize.
• Working with great people and selling in industries that are growing and transforming can completely change your energy. Spaces like AI and emerging technologies are creating opportunities that feel exciting again because you’re learning, growing, and helping shape something new.
• At the end of the day, you have more control over your future than you think. Sometimes finding joy again starts with deciding you’re ready for something better.

“You have control of your future. Don’t give that up to anyone else.” - Donald C. Kelly

Resources

• If you’re feeling stuck or burned out in sales, read Man's Search for Meaning to help reconnect with purpose, fulfillment, and the deeper “why” behind your work.
• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.

Many women in sales struggle with feeling like they’re not fully qualified for leadership roles, even when they’re already doing the work. That self-doubt can make it harder to pursue promotions and career growth. To help break this down, I invited leadership coach and tech executive Erika Chestnut to share the challenges women face when advancing their careers and how sales leaders can better support them.

Meet Erika Chestnut

• Erika Chestnut is a transformational leader with more than 25 years of experience in the tech industry.
• She is passionate about helping individuals and teams rethink leadership, communication, and workplace culture to create stronger performance and long-term success.
• Through coaching, leadership development, and strategic guidance, Erika equips professionals with practical tools to build confidence, strengthen relationships, and lead more effectively.

The Confidence Gap Holding Women Back

• Erika shares how often women underestimate their readiness for leadership opportunities.
• She explains that many women feel like they need to accomplish every requirement before applying for a promotion, while others are comfortable taking the leap much earlier.
• Erika also shares an exercise she uses with clients where they compare their current responsibilities to the role above them. In most cases, women are already doing 50% to 75% of the next position without realizing it.
• Many women feel pressure to constantly prove themselves through performance while still struggling to advocate for their own advancement. Erika explains how this mindset can keep high performers stuck, even when they are already operating at the next level in their careers.

Why Leaders Need to Better Understand Communication Styles

• Communication styles also play a major role in career growth. Erika explains how many leaders unintentionally overlook talented women because they communicate differently from more outspoken employees.
• She also shares how some employees naturally focus on details while leaders are often focused on outcomes. When communication styles do not align, high performers can easily be misunderstood or overlooked.

Treat Your Career Like A Business

• Erika shares advice on how women can become more intentional about career growth by treating their career like a business.
• Set goals, build relationships with mentors and stakeholders, and develop a strategy for long-term advancement instead of waiting to be noticed.

“Success doesn’t come by copying somebody else. Success comes when you know who you are.” — Erika Chestnut

Resources

• Connect with Erika Chestnut on LinkedIn or visit her website to learn more about leadership development, career strategy, and building confidence as you grow into your next role.
• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• 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.

1. 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.

1. 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.