Street Pricing with Marcos Rivera

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.

AI Turbulence: What Delta’s Pricing Experiment Means for SaaS

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.

Don’t Fear the Algorithm: AI, Trust, and the Future of Pricing

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/

Don’t Build on Seats: Why AI Demands a New Revenue Model | Chris Brisson (Salesmsg)

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.

Unlocking the Secrets of Pricing Strategies

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...

From Guesswork to Growth: How AI is Rewriting the Pricing Playbook

Dirty Revenue Is Killing Your Business | Stephen Steers (Steers Consulting)

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

The No Bullsh*t Approach to Business Strategy

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

Why Pricing Deserves a Seat at the Strategy Table | Ali Mamujee (Growth Advisor)

In this episode of the Street Pricing Podcast, host Marcos Rivera speaks with Ali Mamujee, a growth and strategy advisor in the B2B SaaS space. Ali shares his journey from being an early employee at Mercatus, a platform for managing complex renewable energy assets, to becoming a solo advisor for startup growth. The conversation delves into the importance of pricing strategies, the role of data in decision-making, and the value of customer feedback in shaping product offerings. Ali emphasizes the need for alignment within management teams and the significance of removing friction in sales processes to enhance customer experience. In this conversation, Ali Mamujee and Marcos Rivera delve into the intricacies of sales processes, the critical relationship between strategy and pricing, and the importance of crafting a unique value proposition. They discuss the challenges faced by B2B SaaS companies in communicating effectively and the need for a streamlined sales cycle. The conversation also touches on the integration of technology in enterprises and the emotional aspects of sales proposals. Ali shares insights from his experience in entrepreneurship, emphasizing the importance of relationships and embracing the challenges of the 'messy middle' in business growth.CHAPTERS00:00 Introduction to Ali Mamoudji and His Journey02:27 The Genesis of Mercatus and Its Evolution04:51 Navigating Growth and the Importance of Pricing09:54 The Role of Data in Pricing Decisions14:59 The Power of Customer Conversations19:58 Aligning Management Through Pricing Strategy23:49 Streamlining Sales Processes for Efficiency25:45 The Interplay of Strategy and Pricing26:15 Crafting a Unique Value Proposition30:43 The Sales Process as a Product33:15 Communicating Effectively in B2B SaaS35:26 Navigating Technology Integration Challenges38:45 Embracing the Messy Middle of Entrepreneurship TAKEAWAYS Ali Mamujee has a background in B2B SaaS and investment banking. Mercatus aimed to fill a gap in managing complex renewable energy assets. The importance of pivoting and adapting strategies in startups. Data-driven decision-making is crucial for pricing strategies. Customer conversations can reveal valuable insights about pricing. Aligning management teams is essential for effective pricing strategies. Understanding customer needs can lead to better product positioning. Removing friction in sales processes can enhance customer experience. The significance of naming features to enhance perceived value. Regular win-loss interviews can improve sales and pricing strategies. Small tweaks can have a compounding effect on sales cycles. Pricing is the ultimate expression of strategy. Being unique is more valuable than being better. Sales proposals should reflect the ease of the product. Communication in B...

Good, Better, Broken: Why Most SaaS Pricing Fails SaaS Pricing Tiers Are a Trap—Here’s How to Fix Them

In this episode of the Street Pricing Podcast, Marcos Rivera discusses the popular pricing model of good, better, best, particularly in the SaaS industry. He emphasizes the importance of understanding your total addressable market (TAM) and the common mistakes companies make when implementing this pricing strategy. Rivera provides insights on how to effectively structure pricing tiers, avoid overstuffing entry-level plans, and the significance of add-ons. He concludes with a guide to five key principles for successful pricing strategies.   TAKEAWAYS Good, better, best is a popular pricing model in SaaS. Understanding your total addressable market (TAM) is crucial. Avoid overstuffing your entry-level plan with features. Add-ons can help create stair steps for customers. Focus on solving the first few jobs in the customer journey. Keep pricing tiers simple and clear. Aim for two to four pricing tiers for effectiveness. Differentiate plans with clear value propositions. Charge significantly more for the best plan. Regularly review and adjust your pricing strategy.   CHAPTERS 00:00 Introduction to Good, Better, Best Pricing 06:10 Common Mistakes in Pricing Models 12:10 The Guide to Five: Key Principles for Pricing   RESOURCES: 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://www.amazon.com/Street-Pricing-Playlist-Leaders-SaaS/dp/1737528010 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 to CEO, Marcos wants to take the guesswork out of pricing.