In this episode of Thoughts on Selling, I get to sit down with the incredible Kaivona Parker—the Unboring Sales Specialist—and let me tell you, she lives up to the name.
We talk about what it really means to sell without the mask on. Kaivona shares her journey from breaking into tech sales to becoming a voice for underrepresented sellers, and how she’s using enablement to create safe spaces where people can bring their whole selves to work. We swap stories on improv, authenticity, faith, motherhood, and the mental game of sales—and how all of it ties back to showing up real in every conversation.
💡 My Favorite Takeaways
Authenticity wins every time—but you have to give yourself permission to show it.
Sales is improv—every objection is just an offer.
Storytelling > scripts—the right story can make the sale without ever talking specs.
Great leaders create space for others to be themselves.
Your reps’ story matters—start onboarding there, not in the LMS.
🔥 Why This Conversation Stuck With Me
Kaivona said something that’s still ringing in my ears: “When you hold back yourself, you hold back your success.”
That’s it. That’s the post. Too many sales pros are still trying to be someone else’s version of “professional.” This episode is all about breaking that pattern—and why it’s good for both your career and your customers.
If you’ve ever felt like you had to “play a role” in sales, this one’s for you. Give it a listen, and let me know what lands with you most.