You’re listening to the Street Pricing podcast - The only show where proven SaaS leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Enjoy, subscribe, and tell a friend. Now, let’s break it down with your host and sought-after slayer of bad pricing, Marcos Rivera.
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You’re listening to the Street Pricing podcast - The only show where proven SaaS leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Enjoy, subscribe, and tell a friend. Now, let’s break it down with your host and sought-after slayer of bad pricing, Marcos Rivera.
Stop Creating the Boogeyman: How SaaS Sellers Undermine Their Own Pricing | Michael Shields (Tropic)
Street Pricing with Marcos Rivera
38 minutes 43 seconds
1 month ago
Stop Creating the Boogeyman: How SaaS Sellers Undermine Their Own Pricing | Michael Shields (Tropic)
In this episode of the Street Pricing Podcast, Marcos Rivera talks with Michael Shields, VP of Procurement at Tropic, to get the buyer’s perspective on SaaS pricing. Known as the “boogeyman” to sales teams, Michael pulls back the curtain on how procurement sees variability, discounts, and trust.
They unpack why end-of-quarter discounting has created a vicious cycle, how optionality differs from flexibility, and why inconsistent pricing erodes credibility. Marcos and Michael explore the structural fixes—from comp plans to enablement—that help companies sell on value instead of price.
The episode closes with Michael’s concept of the “trust dividend”: when buyers believe in your integrity, sales cycles shorten, margins improve, and negotiation disappears.
CHAPTERS00:00 Introduction – Marcos welcomes Michael Shields from Tropic 00:42 Michael’s background: from manufacturing to SaaS procurement 02:52 What buyers really see in SaaS pricing 06:33 The end-of-quarter discount trap 09:58 The wet towel analogy – why sellers get squeezed 12:09 How sellers created the boogeyman 14:05 Optionality vs. flexibility in pricing 16:32 Discipline and enablement in pricing strategy 18:40 Fixing comp plans and quota pressure 21:34 Negotiation as a crutch for poor value framing 24:47 Training and cross-functional alignment in enablement 26:00 Using AI and conversational data to improve deal discipline 28:30 The trust dividend: transparency as a competitive edge 31:33 How great sales reps get procurement to say “yes” 34:16 Michael’s surprise pick: Les Misérables and the power of story 37:24 Marcos’s wrap-up: discipline, trust, and the remix of Street PricingTAKEAWAYS
Price variability signals weak discipline—and buyers will exploit it.
End-of-quarter deals and last-minute discounts destroy long-term trust.
Structure your discounts with logic (volume, term, bundles), not desperation.
Incentives drive behavior—design comp plans that reward early, clean deals.
Enablement and negotiation training should be ongoing, not one-off.
Review discount patterns with data to uncover value leaks.
Optionality builds trust; flexibility breeds chaos.
The “trust dividend” is real—credibility shortens cycles and raises prices.
Transparency is coming whether sellers like it or not—embrace it as a strength.
Street Pricing with Marcos Rivera
You’re listening to the Street Pricing podcast - The only show where proven SaaS leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Enjoy, subscribe, and tell a friend. Now, let’s break it down with your host and sought-after slayer of bad pricing, Marcos Rivera.
