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.

CHAPTERS
00:00 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 Pricing


TAKEAWAYS

• 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.

In this episode of the Street Pricing Podcast, Marcos Rivera reconnects with Evan Munsing of Corbel Capital Partners to explore the art (and pain) of pricing pivots. From his days as a Marine Corps officer to roles as consultant, operator, and now investor, Evan brings a rare multi-angle perspective on how pricing shapes value creation.

He recounts a company’s evolution from sneaker resale to B2B SaaS, highlighting the shifts from buy/sell arbitrage to transaction fees, revenue share, and finally SaaS licensing. Along the way, Evan and Marcos unpack why revenue share models often break, why certainty is worth paying for, and how investors sniff out pricing problems in the boardroom.

The conversation ends with hard-earned lessons for SaaS leaders: pricing must lead the pivot, not follow it, and nothing reveals the truth about your product faster than charging for it.

CHAPTERS

00:00 Introduction – Marcos welcomes Evan Munsing

01:01 Evan’s background: Marine, consultant, operator, investor

03:59 Pivoting a sneaker resale startup through multiple business models

07:16 From consumer resale to tech-enabled services

09:39 Transaction fees to revenue share

12:32 Pivoting again into B2B SaaS

13:44 The pitfalls of revenue share and value capture

16:11 Raising upfront fees, reducing revenue share

17:26 Growth vs. customer commitment in SaaS pricing

21:17 Why seat pricing misaligns with value

22:47 The CFO’s need for predictability

26:25 Scenario planning, true-ups, and true-forwards

31:18 Pricing as a core part of any pivot

34:45 Pricing as truth: feedback loops from customers

35:57 Boardroom tells that pricing isn’t working

39:17 Evan’s music pick: Jason Isbell, and life lessons from “If We Were Vampires”

40:34 Closing thoughts: value every moment

TAKEAWAYS

• Pricing is strategy, not an afterthought—bring it forward in any pivot.
• Transaction fees, revenue share, and SaaS licensing each come with trade-offs—know when to evolve.
• Value share models create disputes and working capital strain; upfront fees drive customer commitment.
• CFOs crave predictability—companies should structure pricing around certainty, even if it costs more.
• True-up and true-forward models balance flexibility with financial clarity.
• Changing your price reveals real customer value faster than surveys or feedback.
• Investors watch for disappearing KPIs and “too-good-for-too-long” stories as red flags.

In this special episode of the Street Pricing Podcast, host Marcos Rivera is joined by Pricing I/O teammates Emily Sanz and Steve Inman to unpack Delta Airlines’ headline-making decision to roll out AI-powered ticket pricing. With deep backgrounds in airline revenue management, Emily and Steve separate fact from fear, explaining why AI is less about “personal price gouging” and more about sharper segmentation and inventory optimization.

The trio also explore what SaaS leaders can learn from the airline industry—particularly around segmentation, plugging revenue leaks, and the importance of transparent communication when rolling out pricing changes.

CHAPTERS

00:00 Introduction – Delta’s AI pricing controversy

01:00 Emily & Steve’s airline pricing backgrounds

02:48 Why AI is just “revenue management on steroids”

05:09 Inventory, demand, and unit economics

07:14 Busting pricing myths (cookies, Tuesdays, etc.)

10:37 AI and special events (Mardi Gras, Super Bowl, hurricanes)

13:11 Price gouging panic and PR fallout

16:01 Plugging leaks and preventing revenue loss

17:41 Segmentation lessons for SaaS

18:59 Communication: getting it right with customers

20:30 Closing reflections and SaaS takeaways

TAKEAWAYS

• AI in airline pricing is about better segmentation and demand forecasting—not spying on customers.
• Myths like “clear your cookies” or “book on Tuesdays” are folklore, not fact.
• Events, seasonality, and supply/demand shifts are where AI creates the most value.
• Poor communication can undermine even the smartest pricing strategies.
• SaaS leaders should learn from airlines’ mastery of segmentation and apply it to packaging and pricing tiers.
• Knowing and measuring your North Star KPIs is essential for making AI work in pricing.
• Transparency builds trust—without it, customers fill the gap with fear and assumptions.

RESOURCES:
Emily Sanz LinkedIn: https://www.linkedin.com/in/emily-sanz/
Steve Inman LinkedIn: https://www.linkedin.com/in/inmansteven/
Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/

In this episode of the Street Pricing Podcast, host Marcos Rivera speaks with Chris Brisson, CEO and co-founder of Salesmsg. They discuss Chris's entrepreneurial journey, the evolution of pricing strategies in SaaS, and the transition from transactional to subscription revenue models. Chris shares insights on customer behavior, the importance of triggers in pricing, and the impact of AI on business models. The conversation culminates in reflections on triumphs and traps in business growth, emphasizing the need for innovation and adaptability in a rapidly changing market.

In this episode of the Street Pricing Podcast, Marcos Rivera and Mark Stiving delve into the complexities of pricing strategies, emphasizing the importance of understanding customer value and the role of AI in shaping pricing models. They discuss the challenges of defining customer problems, the significance of context in pricing, and the evolving landscape of AI-driven pricing solutions. Mark shares insights from his experiences in pricing education and the development of effective pricing strategies, highlighting the need for businesses to adapt to changing market conditions and customer perceptions.

CHAPTERS

00:00 Introduction to Pricing Insights

01:43 The Power of Pricing Strategies

06:06 Understanding Value and Customer Problems

11:49 Navigating the Challenges of Problem Definition

15:56 The Role of AI in Pricing

21:53 Future of Pricing in an AI-Driven World

24:26 The Importance of Pricing Strategy

28:07 Navigating AI Product Pricing

35:05 Context-Driven Pricing Insights

42:34 Understanding Customer Value

TAKEAWAYS

• Teaching pricing is about bridging the gap for clients.
• Pricing is often more complex than it seems.
• Value is derived from solving customer problems.
• Understanding customer value is crucial for pricing.
• Willingness to pay is influenced by context.
• AI can enhance pricing strategies but requires careful implementation.
• Identifying customer problems is a challenging yet essential task.
• Effective pricing requires understanding market segments.
• Perfection in pricing is unattainable; focus on improvement.
• Context-driven pricing can help align pricing with customer needs.

RESOURCES:
Mark Stiving LinkedIn: https://www.linkedin.com/in/stiving/
Impact Pricing LLC: https://impactpricing.com/
Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/
Marcos Rivera X https://x.com/PRICINGIO
Pricing I/O https://www.pricingio.com/
Street Pricing Book: https://a.co/d/hlMzaM3
Want more information?: info@pricingio.com

The Street Pricing Podcast

Welcome to Street Pricing, the only show where proven SaaS (Software as a Service) leaders share their mindset and mistakes in pricing so we can all stop guessing and start growing. Street Pricing is hosted by Pricing I/O CEO and Pricing Coach, Marcos Rivera, sought after slayer of bad pricing. With 20 years of pricing expertise, he has helped price over 200 SaaS products and coached over 100 SaaS CEOs and counting! From the streets of the Bronx t...

In this episode of the Street Pricing podcast, Marcos Rivera and Stephen Steers delve into the intricacies of sales, focusing on how founders can transition out of day-to-day sales roles while enhancing conversion rates. They discuss the importance of reducing friction in sales processes, the necessity of proper discovery to understand client needs, and the innovative approach of qualifying out potential clients to ensure a better fit. The conversation emphasizes the value of listening to sales calls and utilizing frameworks to improve sales effectiveness. In this conversation, Stephen Steers and Marcos Rivera discuss the importance of building trust in sales through clear deliverables and patience. They explore the role of AI in sales, emphasizing that while it can be a useful tool, it should not replace the human element in building relationships. The discussion highlights key strategies for increasing conversion rates and the significance of maintaining a strong reputation in business.

CHAPTERS

00:00 Introduction to Sales Mastery

03:01 The Art of Firing Yourself from Sales

06:01 Reducing Friction in Sales

09:00 The Importance of Discovery in Sales

12:05 Qualifying Out: A New Approach

15:05 Listening to Your Sales Calls

18:01 Frameworks for Increasing Conversion Rates

20:57 Building Trust Through Deliverables

24:31 The Importance of Patience in Sales

29:07 AI in Sales: A Double-Edged Sword

34:10 Key Takeaways for Sales Success

TAKEAWAYS

• Firing yourself from sales allows founders to focus on growth.
• Reducing friction in the sales process increases conversions.
• Trust is built through consistent actions and communication.
• Proper discovery is essential for understanding client needs.
• Qualifying out clients can lead to better business relationships.
• Listening to sales calls provides valuable insights for improvement.
• Sales objections can be categorized into three main types.
• Packaging offers in a low-risk manner boosts initial engagement.
• Sales frameworks can streamline the selling process.
• Continuous learning from past sales interactions is crucial. Instead of going straight for a retainer, start with a smaller project.
• Clarity in what clients will receive increases conversion rates.
• Building trust takes time and patience.
• AI can be a useful tool but should not replace human interaction.
• Sales success relies on understanding client needs and delivering value.
• Recording and reviewing sales calls can improve performance.
• Establishing a clear process helps clients understand the journey.
• Long-term thinking is essential for sustainable business growth.
• Trust is built through consistent and reliable interactions.
• Patience is a skill that can be developed over time.

RESOURCES:
Stephen Steers LinkedIn: https://www.linkedin.com/in/stephen-steers/
Steers Consulting Group: https://www.stephensteers.com/
Marcos Rivera LinkedIn https://www.linkedin.com/in/marcoslrivera/
Marcos Rivera X https://x.com/PRICINGIO
Pricing I/O

In this episode of the Street Pricing Podcast, host Marcos Rivera speaks with Alex Smith, founder of Basic Arts and author of 'No Bullshit Strategy.' They discuss the importance of strategy in business, the common pitfalls entrepreneurs face, and how to create unique value propositions that stand out in the market. Alex shares his journey from being a strategy consultant to democratizing strategic thinking for entrepreneurs, emphasizing that being 'better' is often a trap that leads to commoditization. The conversation highlights the need for businesses to identify their unique strengths and create solutions that address unrecognized customer needs. In this conversation, Alex and Marcos explore the nuances of business strategy, emphasizing the importance of innovation, self-reflection, and understanding customer value. They discuss how companies can unlock new value by reframing weaknesses and finding their unique position in the market. The dialogue also touches on the challenges tech companies face in differentiating themselves and the pitfalls of overly complex pricing strategies. Ultimately, they advocate for a straightforward approach to strategy that focuses on generating meaningful value for customers.

CHAPTERS

00:00 Introduction to Strategy and Pricing

04:10 The Journey to No Bullshit Strategy

13:44 Understanding Market Positioning

20:34 Creating Unique Value Propositions

26:09 Unlocking Value Through Innovation

29:07 The Importance of Self-Reflection in Strategy

32:37 Navigating the Tech Landscape: Familiarity vs. Uniqueness

34:09 Crafting a Compelling Strategy

38:01 The Right to Exist: Generating New Value

42:25 Debunking Value-Based Pricing

49:34 Personal Touch: Music and Memories

TAKEAWAYS

• Strategy is often overlooked by many entrepreneurs.
• Most businesses operate reactively without a clear strategy.
• Claiming to be the best is often a flawed strategy.
• The market rewards uniqueness, not just superiority.
• Many entrepreneurs fail to differentiate their offerings.
• Customer service claims need factual backing.
• Creating a need can lead to innovative solutions.
• Understanding your unique value is crucial for success.
• Most markets are well-served, making innovation challenging.
• Strategy should be accessible and enjoyable for all entrepreneurs. Innovation can create new market opportunities.
• Reframing weaknesses can lead to unique value propositions.
• Self-reflection is crucial for identifying strengths.
• Successful businesses balance familiarity with uniqueness.
• Tech companies often struggle with differentiation.
• A compelling strategy should be rooted in normalcy.
• Strategy should be presented as a narrative argument.
• Generating new value is essential for business survival.
• Value-based pricing may overlook psychological factors.
• Contextual pricing may be more effective than value-based pricing.

RESOURCES:
Alex Smith LinkedIn: https://www.linkedin.com/in/alex-m-h-smith/
BasicArts Website: https://basicarts.org/
The Hidden Path Newsletter: https://basicarts.org/newsletter/
Marcos Rivera LinkedIn