In this episode, I had a great conversation with Tim Bradley, founder of Pennant—a video marketing firm that’s laser-focused on helping companies improve conversion rates in the middle of the funnel. Tim’s all about storytelling, yes—but with a clear eye on how that story supports sales performance.

We talked a lot about the line between marketing and sales enablement, and how the best content—especially video—can serve both when it’s done right.

• Video as a Sales Tool: Tim broke down his “video marketing trifecta”: Anthem (why you exist), Explainer (what you do), and Endorsement (proof you work). These aren’t just for brand awareness—they’re tools for sales teams to build trust and clarity with buyers throughout the journey.

• Marketing vs. Enablement: We got into the distinction—and overlap—between traditional marketing assets and true sales enablement content. Great video doesn’t just influence customers; it reinforces key messages for reps too. When reps know the story and understand the pain points it addresses, they sell more confidently.

• Improving Conversion, Not Just Filling the Funnel: As I said in the episode, you can throw money at lead gen and still fall short. Or you can get smart about where the funnel leaks—and use content to improve handoffs, clarify value props, and speed decision-making. Tim’s all about enabling that kind of lift.

• Personalized Video for Reps? Yes! Tim strongly encourages sales reps to use video in their outreach. It doesn’t have to be polished—it has to be relevant and human. A personalized message delivered with care can cut through the noise and create meaningful engagement.

• Storytelling = Risk Reduction: When buyers feel understood, they feel safer. We talked about how storytelling helps reduce perceived risk, which is often what actually drives buying decisions—not feature checklists.

One of my favorite parts of this episode was hearing Tim share a recent client success story—a Fortune 30 sales kickoff video that drove real excitement and alignment across the sales team. The video helped a new marketing leader make a killer first impression and gave the sales team tools they were genuinely excited to use.

If you’re in sales or sales enablement, this conversation will give you real-world insight into how content and story can drive performance. Video is a powerful lever, not just for reaching buyers but for equipping your team to sell more effectively.

🎧 You can find Tim at pennant.video or connect with him on LinkedIn.

As always, let me know how you're bringing these ideas to life in your work!

Until next time—
Lee

In this episode of Thoughts on Selling, I sit down with sales coach and former VP of Sales, Shane Jamison, to talk about the real work behind sustainable sales—coaching to the numbers, managing pipeline pressure without compromising relationships, and becoming the guide your customer needs.

We dive into what it means to stay authentic when management wants pull-ins, how to balance urgency with trust, and why pressuring a customer to act early can create more harm than good.

Shane shares lessons from his time building and leading teams, and how his passion for coaching emerged from a love of helping people do more than just hit quota—helping them discover where they thrive.

👉 Key Takeaways:

• Align deal timing to customer priorities, not fiscal quarter deadlines.

• Pressure testing a deal timeline isn’t pushy—it’s collaborative.

• Discounts rarely drive true urgency in B2B—clarity does.

• Coaching is about surfacing what reps already know and helping them apply it with confidence.

• Sometimes the best coaching outcome isn’t closing a deal—it’s helping someone realize they’re in the wrong role.

✅ Action Items:

• Revisit your pipeline: Are close dates based on your internal quarter or the customer's implementation needs?

• When coaching reps, shift the conversation from "what can you close?" to "where can we create value now?"

• For managers and sellers alike: take 30 minutes to map the actual steps it takes from verbal commit to closed-won—then build backward.

In this episode of the Thoughts on Selling podcast, I welcome Steven Ethridge, an accomplished sales trainer, coach, and expert in Neuro-Linguistic Programming (NLP). Our conversation dives into the pivotal roles that mindset and intentional communication play in driving meaningful sales outcomes.

Steven shares his structured two-part methodology: Sales Mindset Self-Mastery and his NLP-based Five-Step Sales Process. He highlights how a salesperson's internal belief system shapes external performance and how aligning communication with a buyer's motivations fosters authentic connections and improved results.

Key discussion points:

• Mindset as a foundation. Steven explains how reshaping internal narratives and removing limiting beliefs can dramatically enhance sales performance.

• Building rapport effectively. We discuss the importance of observing and mirroring both verbal and non-verbal cues to establish deep, authentic rapport.

• Tailoring communication. Steven emphasizes the need to adapt language to a prospect’s preferred style—whether visual, auditory, or kinesthetic—for greater influence.

✅ Key takeaways:

• A strong, intentional mindset is crucial for long-term sales success.

• Sales is most effective when it is a collaborative, value-driven process.

• Attuning your communication style to match that of your prospect can deepen trust and engagement.

To explore Steven’s sales training programs, visit ethridge.com.

Thank you for listening to this episode. I look forward to hearing how you incorporate these strategies into your sales approach.

— Lee

Welcome back to Thoughts on Selling. This one’s a little different — and a little deeper. I had the chance to sit down with fellow ultrarunner, entrepreneur, and coach Troy Meadows to talk about something foundational: your why — personally, professionally, and organizationally.

Just like an ultramarathon, building something meaningful in sales (or life) demands more than tactics. You need a reason to keep going when it gets hard. And believe me, it will get hard.

🏃‍♂️ Key Takeaways

• Your “why” is your North Star: Whether you're selling software or running 100 miles, the why behind your effort determines how you show up when it gets tough.

• Good sales isn’t about features — it’s about values: If your customer’s why and your company’s values align, magic happens. Think 20-year partnerships, not transactional closes.

• Hire for values, not just skills: High performers who aren’t aligned to the mission will quietly (or loudly) tank your culture and your customer experience.

• The "family provider" and "community role model" stories that show how powerful a personal why can be.

• Troy’s perspective on vesting sales commissions over time to drive customer-centric behavior.

• A classic Merck example that shows what institutional alignment really looks like — and how sales reps need to meet their customer’s mission head-on.

• Leaders: Post your values where your team and your customers can see them — literally. Make them part of the conversation.

• Sellers: Stop pitching and start listening for your customer’s why. Align there, and the deal follows.

• Marketers: Build messaging from the inside out — starting with mission, vision, and values, not product specs.

• Everyone: Revisit your personal why often. It evolves. Make sure your work still serves it.

🏔️ Big thanks to Troy for helping me stretch this episode beyond the usual sales playbook. If you're into running, business building, or just figuring out what makes you tick, check out the Mid Packer Pod and connect with him on LinkedIn.

As always, I’d love to hear what resonated for you — and what action you’re taking next.

Dustin Beaudoin joined the Thoughts on Selling podcast to discuss the intersection of AI and sales strategy, the critical importance of in-depth preparation, and how these elements are shaping the future of sales. Here’s a deeper dive into our conversation:

Dustin's Background and Sales Philosophy

• Dustin Beaudoin, with his extensive background in enterprise SaaS sales, brings a unique perspective to the sales process, particularly through the lens of strategic enterprise sales. His journey through the ranks of sales has made him a staunch advocate for leveraging AI to enhance sales effectiveness.

• He shares insights on how he has developed a passion for integrating AI into sales to make strategic engagements more impactful. His approach revolves around smart utilization of technology to augment the human elements of sales.

Deep Preparation in Sales

• Dustin emphasizes that successful sales strategies heavily rely on meticulous preparation. This involves understanding not just the overarching goals of the organizations but also the nuanced needs of the individuals within these organizations.

• Effective preparation includes researching potential clients’ business models, their industry challenges, and the specific pain points of the contacts within these companies. Dustin points out that this level of preparation allows salespeople to approach discussions with valuable insights and tailored solutions that resonate on a personal level with the client.

Strategic Utilization of AI

• Our discussion highlights the transformative potential of AI in reshaping sales strategies. Dustin is particularly interested in how AI can be used to prepare for sales interactions more effectively, ensuring communications are timely and relevant.

• The conversation explores how AI could automate the gathering of strategic information, thus allowing sales professionals to focus on creating more personalized engagement strategies. This is not just about automating tasks but enriching the quality of interactions.

Key Takeaways and Practical Advice

• Preparation is key: Both Dustin and I agree that whether you are a seasoned account manager or a sales development representative (SDR), preparation is non-negotiable. Coming to each conversation with a robust, researched point of view is crucial.

• Quality over quantity: It’s essential to focus on the quality of sales interactions rather than just the volume. High-quality, well-researched interactions are more likely to build trust and lead to successful outcomes.

• AI as a strategic enhancer: Smart deployment of AI can make a significant difference in how sales teams operate. AI should be used to enhance strategic engagement, not replace the human elements that are vital to building relationships.

The Future of Sales with AI

• Dustin shares his vision for the tools he is developing, aimed at enhancing the capabilities of sales professionals through AI. These tools are designed to help salespeople be better prepared and more responsive to client needs, using AI-driven insights to inform their sales strategies.

Engage with Dustin's Work

• For those interested in strategic sales and AI, Dustin’s ongoing work and insights could be incredibly beneficial. Reaching out to him on LinkedIn or via email provides opportunities to learn more about the integration of AI in sales strategies.

This conversation underscores the importance of blending traditional sales techniques with innovative technologies like AI to stay ahead in the competitive landscape of sales. The key is to maintain a balance where technology enhances human capabilities without overshadowing the essential human touch that is so crucial to building and maintaining strong client relationships.

I sat down with my good friend and former Oracle teammate Jane Scott for a deep dive into customer success. Jane and I worked together for years on the key account team supporting Xerox, and she was the glue that held it all together — truly the most important person in the room.

We covered a lot in this conversation: from the foundational elements of long-term account management, to the evolving role of customer success in today’s SaaS world. Jane brings a wealth of experience and a refreshingly candid perspective on what it takes to really support customers.

Here are a few key points we dug into:

• Why consistency and historical knowledge matter — and how Jane’s 12 years on a single account gave her unmatched influence and insight.

• How customer success is about enabling outcomes, not just solving problems.

• The importance of aligning to the customer’s business rhythm and strategic objectives.

• Why some SaaS companies may not need a dedicated CS team — but the function must still be owned somewhere.

• How internal alignment between sales, operations, and product impacts the customer experience.

Takeaways:
✅ Understand the rhythm of your customer’s business — timing is everything.
✅ Great customer success starts with empathy and ends with results.
✅ Whether or not you have a CSM team, someone needs to own the customer journey.
✅ The best relationships go beyond QBRs — think industry events, shared learning, and meaningful connection.
✅ Ask early: “What will keep us from being successful together?”

🌟 Jane reminds us: “It doesn’t have to be a huge, elaborate plan. Sometimes it’s just asking, ‘How can I help?’”

🔗 Connect with Jane: LinkedIn

Thanks for tuning in — don’t forget to subscribe, share, and leave a review if you’re enjoying the podcast. Until next time!

Welcome back to another episode of the "Thoughts on Selling" podcast. In this episode, we delve into the nuanced world of sales negotiations with Ron Hubsher, a seasoned expert in the field.

Here’s a detailed breakdown of our conversation and the key insights we uncovered.

Introduction to Sales Negotiations:Ron introduces himself as an engineer turned sales professional who applies engineering principles to sales, advocating for a systematic approach to sales akin to a manufacturing process. This ensures consistent, quality outcomes through qualified opportunities and repeatable best practices.

The Underappreciated Art of Negotiation Training:Ron observes that while many sales professionals have undergone various forms of sales training, few have deeply explored negotiation training. He highlights the complexity of negotiations, comparing it to different branches of mathematics, where skills range from basic arithmetic to complex calculus. He stresses that negotiations in sales differ significantly from conflict resolution or transactional negotiations, which often have higher stakes or simpler transactional goals.

Integrating Sales and Negotiation:Ron emphasizes that everything omitted in the sales process will surface during negotiations. He advocates starting with the end in mind, ensuring that every step of the sales process aligns with the final negotiation, thus avoiding last-minute concessions and emphasizing value over price.

Negotiation as an Ongoing Process:Ron and Lee discuss that negotiation isn't just a phase but an integral part of the entire sales process. Effective negotiation involves understanding both the business impact and personal stakes for the buyer, leveraging these insights to align the sales approach closely with the buyer's needs and minimizing their perceived risk.

The Importance of Personal Connections:A significant part of the discussion revolves around the personal connections that salespeople must forge with their clients. Understanding both the professional and personal motivations of buyers can dramatically shift the dynamics of a sales negotiation, making it more about mutual benefit and long-term relationships rather than a one-off transaction.

Insights on Discovery and Value Proposition:The conversation also covers the importance of discovery in sales, where understanding the client's needs goes beyond superficial interactions. Effective discovery involves deep listening, asking the right questions, and positioning oneself as a facilitator who helps clients articulate and understand their own needs better.

Takeaways:

• Prepare Thoroughly for Negotiations: Anticipate potential challenges in the negotiation phase by addressing them early in the sales process. This preparation prevents surprises and builds a stronger value proposition.
• Focus on Reducing Buyer's Risk: Tailor your approach to minimize both the business and personal risks for the buyer. This strategy shifts the focus from selling to helping, thereby fostering trust and partnership.
• Build Personal and Business Agendas: In negotiations, recognize and address both the stated business objectives and the unstated personal goals of the buyer. This dual approach can significantly enhance the relevance and appeal of your proposal.
• Negotiation is Relational, Not Transactional: Foster a negotiation environment that views success as a mutual achievement rather than a zero-sum game. This perspective encourages ongoing relationships and future business.
• Use Discovery to Build Value: Continuously engage in discovery throughout the sales process to better understand and respond to the customer’s evolving needs and conditions, ensuring that your solutions remain aligned with their goals.

These insights underline the importance of a sophisticated, integrated approach to sales and negotiations, emphasizing preparation, personal connection, and a deep understanding of the client's business and personal risks.

In this episode, I sit down with Steven Werley, a sales expert, entrepreneur, and endurance athlete with a background in both marketing and military service. We dive into why pushing yourself to do hard things—whether in sports, business, or sales—builds resilience and long-term success.

Steven shares his insights on the role of AI in sales, explaining that AI isn’t here to replace salespeople but to help them perform better. By automating follow-ups, streamlining call reviews, and taking over tedious CRM tasks, AI allows sales teams to focus on high-value interactions. We also discuss his latest project—a new podcast where he builds AI tools for businesses live on air.

• Sales is about helping, not just closing. The best salespeople focus on real conversations and problem-solving, not just pushing a pitch.
• AI is a game-changer, but not a replacement. AI can handle time-consuming tasks like tracking call insights, drafting follow-up emails, and managing CRM updates—freeing up salespeople to focus on selling.
• Efficiency + effectiveness = better sales. Companies that embrace AI-driven insights can improve both their processes and performance, helping teams work smarter.

✅ Sales is human-first. AI can enhance the process, but people still buy from people.
✅ The best sales reps embrace AI. Those who adapt and leverage AI will gain an edge over the competition.
✅ Doing hard things prepares you for success. Whether it’s endurance sports, military service, or pushing through tough sales cycles, resilience is key.

🔗 Connect with Steven:
👉 LinkedIn | Facebook

If you enjoyed this episode, subscribe, share, and leave a review!

In this episode ofThoughts on Selling, host Lee Levitt is joined by Todd Busler, founder of Champify. Todd shares his journey from sales engineering to leading revenue organizations and launching a company designed to revolutionize outbound sales efficiency.

Lee and Todd dive into the evolving nature of sales, the importance of coaching over managing, and why the best salespeople are often ex-athletes, musicians, or gamers. They also explore how reps can leverage relationships and first-party data to improve efficiency in an increasingly difficult outbound sales environment.

Key Takeaways

1. The Art of Selling Hasn’t Changed – But the Tools Have

   • Sales is still about relationships, trust, and persistence. While AI and automation can assist, the best reps still prioritize human connection.
   • The most effective sellers don’t rely on scripts; they deeply understand their customers and help them solve real problems.

2. Great Sales Leaders Coach, Not Manage

   • The transition from top-performing rep to manager can be tough—many fall into the trap of becoming a "super rep" instead of a true coach.
   • The best leaders create a culture of accountability, continuous learning, and execution rather than micromanaging or seeking to be liked.

3. Outbound Sales is Harder – But Relationships Unlock Success

   • Traditional outbound strategies are less effective than they were 5-10 years ago. The best reps leverage past relationships, advocates, and past customers who already know and trust them.
   • Tools like Champify systematize what great reps do naturally—tracking job changes and using existing relationships to warm up cold outbound efforts.

Actionable Insights

• If you’re a sales rep, commit to continuous learning—whether through listening to podcasts, reading, or studying top performers.
• As a sales leader, prioritize enablement and structured coaching. The best results come from investing in A-players rather than spending too much time trying to "fix" C-players.
• If you’re running an outbound motion, take a hard look at how you’re leveraging existing relationships. Are you tracking past champions and advocates in your pipeline?

Resources Mentioned

• Book:High Probability Sellingby Jacques Werth
• Podcast:For The Long Run(Exploring ultra-running as a metaphor for life and sales)
• Tool:Champify – Helping sales teams tap into past customers and advocates
• Conference: GTM 2024Pavilion Conference in Austin, TX

Connect with Us

• Visit our website:podcast.thoughtsonselling.com
• Connect with Lee Levitt:LinkedIn
• Connect with Todd Bussler:LinkedIn

If you enjoyed this episode, take a moment to leave a review -- it helps others find and benefit from the show. And, please, share this episode with a colleague who could use these insights!

Take one or two key insights from this episode, apply them in your sales role, and let us know how it impacts your success.

Thanks for tuning in!

In this episode, I had an amazing conversation with Estefania (Fani) Rodriguez Marino, a sales enablement pro joining in from Paris.

We talked about what sales enablement really means and how it’s not just about training or content—it’s about helping the company achieve its goals by aligning sales efforts with strategy. Fani shared her journey, her passion for embracing challenges, and why motivation and context are crucial for sales success.

One of the biggest takeaways from our conversation is how sales enablement needs to balance scalability with personalization. While it’s easy to create one-size-fits-all training programs, real impact comes when we tailor initiatives to the individual needs of sales reps.

We also discussed the importance (and power!) of listening—not just hearing words, but truly understanding what prospects and sales teams need to succeed.

Another key point we touched on is how sales enablement is really about selling change to sellers. Just like in sales, we have to position new tools and processes in a way that resonates with reps and helps them see the benefits. Fani emphasized that salespeople need to understand their role within the bigger picture to stay motivated and engaged.

Key Takeaways: