53. Storytelling that Sells: Enabling Reps Mid-Funnel

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