Description

In this episode of Sales & Cigars, Walter Crosby sits down with Nick Massaro of Membrane for a candid, no-BS conversation about what actually holds good salespeople back. From early sales foundations and structured training to the mindset traps that quietly derail deals, this episode digs into the space between opening and closing—the part most reps avoid and where deals are truly won or lost.

Nick shares his journey into sales, the evolution of his mindset, and the hard-earned realization that being "the most liked rep" is often a sign something went wrong. Together, they unpack the dangers of approval-seeking, why discomfort is part of great selling, and how modern buyers require a different kind of leadership from sales professionals.

This is a grounded, honest conversation for salespeople who want to stop getting compliments instead of contracts.

Episode Highlights

• Why "You were the best rep" is often a kiss of death
• The difference between opening deals and advancing them
• How early structure shaped Nick's sales foundation
• The mindset shift required to lead buyers without controlling them
• Why avoiding money conversations quietly kills deals
• Selling outcomes vs. selling features—especially in complex software
• Letting go of approval to ask better questions
• What great sales and good parenting surprisingly have in common

Key Takeaways

• Being liked doesn't equal being effective
• The middle of the deal—not the open or close—is where salespeople grow
• Approval-seeking prevents tough (necessary) conversations
• Buyers are in control—but salespeople must still lead
• Discovery isn't about sounding smart; it's about creating clarity
• Authenticity beats polish every time
• Process creates freedom, not rigidity

Who Should Listen

This episode is for:

• Salespeople who hear "we loved you" more than "we're buying"
• Reps who love prospecting but struggle with deal momentum
• Sales leaders coaching mindset, not just activity
• Anyone selling complex or non-commodity solutions
• Business owners trying to understand what their sales team is really up against

About the Guest

Nick Massaro is a sales professional at Membrane with a background spanning insurance, SaaS, and sales-as-a-service environments. Known for his authenticity and curiosity, Nick brings a thoughtful perspective on modern selling—one rooted in structure, accountability, and continuous improvement.

Connect with Nick

• Nick Massaro on LinkedIn
• Membrane

Connect with Walter Crosby and Sales & Cigars:

• Website: Helix Sales Development
• LinkedIn: Walter Crosby
• Instagram: @wcrosby248
• Facebook: Helix Sales Development

Share Your Thoughts:

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Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.