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 

SUMMARY 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

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...

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.

In this episode of the Street Pricing Podcast, host Marcos Rivera interviews Nikita Bykadarov, CEO of Maildoso, a startup focused on improving cold email deliverability. They discuss the challenges of cold email marketing, pricing strategies, customer acquisition, and the importance of deliverability in email campaigns. Nikita shares insights from his journey, including the evolution of Maildoso's offerings, growth metrics, and the value of customer education. The conversation emphasizes the need for startups to focus on solving core problems and adapting to customer needs.   Takeaways Maildoso helps ensure cold emails land in inboxes, not spam. Pricing strategies evolved from annual to quarterly based on customer feedback. Customer acquisition cost is low due to effective cold email strategies. Maildoso has grown to over 3,000 customers in under a year and a half. Deliverability is the core value proposition of Maildoso Customer education is key to improving email marketing success. Nikita emphasizes the importance of managing stress as a startup founder. The company focuses on solving the core problem of email deliverability. Maildoso’s growth is driven by a commitment to value and customer success. Iterative improvements in pricing and offerings are essential for growth.   Chapters 00:00 Introduction to Cold Email Solutions 03:03 Pricing Strategies and Customer Acquisition 05:55 The Evolution of Maildoso's Offerings 09:10 Growth Metrics and Customer Success 12:05 Challenges and Future Plans 15:02 Deliverability and Customer Education 17:46 Reflections and Advice for Future Entrepreneurs   Resources: Nikita Bykadarov LinkedIn: https://www.linkedin.com/in/nikita-maildoso-2b6a6755/ Maildoso Website: https://getmaildoso.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: ...

Why does Rob Walling call pricing "the biggest lever in SaaS" and how often does he recommend revisiting your pricing strategy?  In this value-packed episode of the Street Pricing Podcast, Marcos Rivera interviews Rob Walling, founder of Drip and TinySeed accelerator, who shares how changing his SaaS pricing model from "new subscribers" to "total subscribers" transformed his business. Rob reveals the psychological hurdles he faced before implementing the change and the expansion revenue that followed, emphasizing that pricing is "the biggest lever in SaaS."   Beyond pricing, Rob unpacks his framework for diagnosing and breaking through SaaS plateaus, offering his "Big Five" marketing approaches for B2B growth. The conversation concludes with Rob's perspective on AI's impact on SaaS—predicting short-term challenges but long-term opportunities for founders who adapt as business models evolve from traditional interfaces to APIs and agent-based interactions.  In this episode: (00:00) Introduction to Rob Walling, renowned entrepreneur and investor, highlighting his contributions to the SaaS and startup ecosystem. Rob shares his mission to empower independent startups through his work with TinySeed, MicroConf, and the podcast "Startups for the Rest of Us." (11:55) Overcoming Pricing Anxiety in Startups - Rob shares personal experiences with pricing strategy development, focusing on the importance of overcoming fear to unlock growth potential. The conversation explores the impact of expansion revenue and the necessity of clear communication during pricing changes.  (21:02) We delve into strategies for navigating growth challenges in SaaS businesses. Rob stresses the importance of regular pricing strategy adjustments and the role of strategic marketing in driving business expansion.   (27:42) Effective marketing strategies for B2B SaaS companies - known as the "big five": content, SEO, cold outreach, integrations and partnerships, and ads. Rob shares insights into tailoring these strategies to specific business contexts and stresses the importance of adaptability and quick execution to avoid stagnation.  (36:34) The transformative impact of AI on the SaaS industry, drawing parallels with past technological revolutions. Rob expresses some of the challenges and opportunities AI presents for existing business models and underscores the importance of adaptability for future success.  (38:32) Rob shares his favorite jam by Third Bass, an unexpected musical choice  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 guessing out of pricing.   Resources: Rob Walling LinkedIn: https://www.linkedin.com/in/robwalling/  TinySeed Website: https://tinyseed.com/  MicroConf: https://microconf.com/ Startups For the Rest of Us Podcast:  https://www.startupsfortherestofus.com/ 

Is your pricing metric actually tracking what delivers the most value to customers—and could a misalignment be causing hidden churn?  Join me for a data-driven conversation with Pricing I/O data ninjas Sam Blumenfeld, Matthew Duncan, Kyle Eustaquio, Nishita Katere, Jack LoGrasso and Brenden Murden. We demystify what "good data" actually means for SaaS pricing decisions. The team unpacks how to transform "crappy" data into actionable insights by unifying fragmented datasets, tracking feature usage patterns, and analyzing lost deals.   You’ll hear practical survey guidance with specific recommendations on sample sizes, survey length (keep it under 15 minutes!), and when to use methodologies like conjoint analysis versus Van Westendorp. For SaaS leaders struggling with packaging decisions, the experts explain how to identify value patterns in usage data and leverage AI for real-time competitive analysis while maintaining human oversight. This episode delivers concrete frameworks for moving beyond pricing guesswork to data-driven strategy.  In this episode:   (00:00) Marcos introduces six data leads from Pricing I/O who collectively analyze massive amounts of pricing data. Each team member shares their background, from strategic finance and investment analysis to market research and biotech.  (04:05) Navigating the data landscape - “Happy vs. Crappy” - Critical aspects of data quality for pricing analysis, emphasizing the importance of unified data with consistent account IDs, tracking both absolute and relative feature usage, and collecting lost deal information to understand what products aren't selling well.  (19:09) Tips on creating effective pricing surveys, including keeping surveys under 10-15 minutes to avoid respondent fatigue, using neutral language in questions, and adjusting survey methodology based on expected sample size.  (29:11) Examining different pricing survey methodologies, focusing on conjoint analysis for determining feature value.  (36:00) Benefits of customer surveys versus expert interviews, insights on how customer surveys force companies to think from the customer's perspective, while expert surveys provide deeper, more invested responses.  (40:30) “Get out of my way-I” - How AI is transforming pricing analytics by accelerating insights and putting data at the forefront of decision-making.  (44:44) AI applications for competitive data analysis, real-time price adjustments, and processing large datasets, while addressing data privacy concerns when utilizing AI systems for client information.  (45:55) Favorite current jams from the team!   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 guessing out of pricing.    Resources:  Sam Blumenfeld: https://www.linkedin.com/in/sam-blumenfeld/  Matthew Duncan: https://www.linkedin.com/in/matthew-david-duncan/  Kyle Eustaquio:

Why did Peter Bonney decide to pivot from usage-based pricing to a flat, user-based model, and how has this shift impacted Fastbreak RFP's growth and customer satisfaction?Join me for a candid conversation with Peter, who's transforming how enterprises handle RFPs (Requests for Proposals) through intelligent pricing architecture. After seeing enterprises struggle with opaque, usage-based pricing models in the RFP space, Peter built Fastbreak RFP to introduce predictable, user-based pricing that scales with customer success. We unpack key insights into RFP pricing models, including: - The hidden costs and challenges of usage-based pricing in RFP software - How the shift from usage-based to user-based pricing impacts customer retention - Real-world examples of simplifying compliance workflows through pricing structure Peter shares his framework for building pricing tiers that align with procurement workflows, demonstrating how Fastbreak RFP reduced sales friction through transparent pricing architecture. For pricing leaders wrestling with the complexity of enterprise RFP solutions, Peter reveals his playbook for packaging AI capabilities without creating pricing anxiety. Whether you're rethinking your pricing strategy or seeking insights on monetizing AI features in enterprise software, this discussion offers actionable frameworks for modern SaaS pricing architecture in complex markets. In this episode: (00:00) Introduction of Peter Bonney, Founder and CEO of Fastbreak RFP   (03:46) Rewind story, Peter's entrepreneurial journey and evolution of Fastbreak’s pricing strategies, the chaotic nature of enterprise RFPs and Fastbreak RFP's automation solutions   (16:21) Resolving pricing misalignment, pricing models in AI-driven businesses and the transition from usage-based to user-based pricing  (20:41) Challenges in simplifying pricing models for large companies and the benefits of tiered seat models, transitioning to user-based pricing for clarity and predictability  (26:00) Future of pricing models, leveraging AI for “magical” RFP responses and CRM integrations to create tailored responses   (31:05) Closing remarks, favorite jam by Living Colour 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 guessing out of pricing.   Resources:Peter Bonney LinkedIn Fastbreak RFPMarcos Rivera LinkedIn

How can SaaS companies benefit from the seasoned insights of the Pricing I/O team to navigate complex market dynamics and achieve pricing excellence?   Today I’m speaking with Peter Cohen, Steve Inman, Mario Pereda, Emily Sanz and Amit Saraf - a special lineup of pricing experts from the Pricing I/O team. These experts have vast knowledge across various industries like airlines, freight transportation, and tech. Each of my talented colleagues shares their unique insights into the art of pricing. We engage in a dynamic roundtable discussion, unraveling the intricacies of delivering just the right amount of value without overextending, a vital strategy for maximizing utility in SaaS pricing. Our conversation reveals how to effectively capture value and tackle the complexities of pricing across different sectors, guiding SaaS companies toward optimal pricing models.  The discussion begins with a deep dive into why software packaging deserves more attention than pricing itself, with the team advocating for an 80/20 split in favor of packaging considerations. They explore why providing the right amount of value, rather than maximizing features, is crucial for customer satisfaction and revenue growth in SaaS businesses.  The conversation then shifts to analyzing Salesforce's recent move to conversation-based pricing for their AI agent service, charging $2 per conversation instead of traditional user-based licensing. The team debates the implications of this shift and whether it would work for smaller companies without Salesforce's data advantages and established customer base. The episode concludes with team members sharing their key advice for SaaS leaders in 2025, including the importance of customer feedback, service differentiation, careful discounting practices, and implementing effective pricing committees.  In this episode: (00:00) Team Introductions - Pricing I/O team members including Peter Cohen, Steve Inman, Mario Pereda, Emily Sanz and Amit Saraf - each bringing different pricing expertise across industries  (05:09) “A-ha” moments, packaging vs pricing, why software packaging deserves more attention than pricing levels, with the recommendation to spend 80% of time on packaging and 20% on price points, why giving customers the right amount of value (no more, no less) is crucial for SaaS success  (17:41) Salesforce's move from user-based licensing to charging $2 per conversation for their AI agent, the pros and cons of this pricing strategy and its implications for the industry  (31:38) Team members share their top pricing recommendations for 2025, including:  - Getting customer and employee feedback regularly  - Focusing on services as a differentiator  - Being careful with discounting  - Implementing a pricing committee  (37:16) Closing remarks, favorite jams  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 guessing out of pricing.    Resources:  Peter Cohen LinkedIn: https://www.linkedin.com/in/peter-co...

How can entrepreneurs unlock exponential growth by understanding and leveraging “discovery-led growth” in their pricing strategies? Today, Street Pricing listeners are treated to Marcos’ discussion with Eric Weiss, CEO of Chaos to Clarity. Eric delves into the intricacies of entrepreneurial growth with an emphasis on understanding customer value. Drawing from his extensive experience, Eric highlights the transformative power of human-centered design through compelling case studies, such as differentiating an email marketing platform in a crowded market. Marcos and Eric also explore how companies can leverage customer feedback to enhance user experience and retention, advocating for a ‘discovery-led growth’ mindset.  Later in the episode, Eric provides valuable insights into the challenges and potential of AI in product development. Incremental integration is key to ensure reliable user experiences. You’ll hear the importance of empathy, strategic design, and continuous learning to achieve product-market fit and unlock market potential. This episode is a must-listen for entrepreneurs seeking to harness innovative strategies for growth and value capture.In this episode:(00:00) Guest intro of Eric Weiss, CEO of Chaos to Clarity (04:10) Rewind story, the importance of customer value as a driver for pricing strategies and growth, free master classes (15:26) Creating better interfaces, how companies can enhance user experience and retention through customer feedback, simplified onboarding, maintaining a discovery-led approach with continuous customer engagement (20:43) How you can start your discovery-led growth - talk to your customers! Speak their language, ask the right questions, find the custom solution for them  (29:30) What’s going on today - Delving into the challenges of AI integration, the importance of balancing innovation with consistent user experiences, and avoiding customer churn, AI “Agency” - allowing to take steps for you (41:37) Know your customer better than they know themselves -  empathy in understanding customer needs and crafting elegant solutions, aiming to be the best in the market, value of knowing your customer and being a master in your field (44:38) Closing remarks, favorite jam from MetallicaWelcome 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 guessing out of pricing.   Resources:Eric Weiss LinkedIn Chaos to Clarity Marcos Rivera LinkedIn Marcos Rivera X Pricing IO

How did James McKay revolutionize financial services with his "20-minute term sheet" strategy, and why is speed more valuable than cost in today's financial landscape?   James is the CEO of VEN, and he joins me on today’s Street Pricing podcast to navigate the complex world of Revenue Operations (RevOps) and pricing strategies. Together, we chart the course from James' time at Clearco, where he revolutionized financial services with innovative pricing strategies, to his current focus on optimizing RevOps. Learn how the "20-minute term sheet" became a game-changer in providing rapid access to capital and why speed and flexibility are often valued more than the cost itself in financial services. James reveals the challenges of targeting more sophisticated clients and the vital role of clearly articulating a value proposition to overcome cost objections. Delve into tales of adapting pricing and packaging in response to market dynamics. RevOps emerges as the backbone of operational efficiency throughout these transformations.   In this episode:  (00:00) Guest intro of James McKay (03:34) Rewind story, navigating pricing strategies for growth, "20-minute term sheet" campaign, challenges targeting larger companies, importance of speed and flexibility in financial services (10:31) Defining revenue operations (‘RevOps’), optimizing for growth, defining a new business category, challenges in raising capital, and the role of RevOps in managing the customer journey (14:31) RevOps best practices and timing, managing customer interactions, data governance, and infrastructure for companies transitioning to a repeatable sales process (17:49) Founder-led sales transition complexity and timing, common issues and challenges, CRM data and customer journey mapping, CRM systems must accurately reflect the customer journey, measure funnel metrics, and balance automation with user adoption (27:46) Managing sensitive data, a RevOps terminology debate (33:26) Impact of AI on RevOps Professionals, RevOps is crucial for sales strategy, using a pragmatic approach and small improvements for growth (40:24) Future growth and favorite jams  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 guessing out of pricing.     Resources: James McKay LinkedIn VEN  Marcos Rivera LinkedIn Marcos Rivera X Pricing IO Book: Street Pricing Email Street Pricing for a consultation  

How can defining an ideal customer profile (ICP) transform your SaaS pricing strategy and ensure your product's value is validated by early paying customers? Niclas Lilja, the visionary Founder and CEO of Younium, shares insights on the evolving dynamics of SaaS pricing strategies. An industry trailblazer, Niclas illuminates his transformative journey from Medius to Younium, and shifting from traditional subscription models to innovative usage-based pricing. We get into the complexities of pricing decisions, looking at the balance between clarity and complexity. Niclas shares his art of iteration, negotiation, and maintaining alignment with customer success. You’ll hear about defining an ideal customer profile (ICP) and securing early paying customers to validate a product's value and the evolution of defining an ICP over time. We delve into the psychological dynamics entwined with usage-based pricing and its diverse impact on companies of varying sizes. In this episode: (00:00) Niclas Lilja, CEO of Younium, shares his journey from Medius to founding Younium, the transition from traditional subscription models to innovative usage-based pricing, and clarity over complexity in pricing decisions (11:36) Developing an Ideal Customer Profile (ICP) and an effective pricing strategy, securing early paying customers to validate a product's value, refining pricing models is an evolving process that can take years.  (16:59) Niclas’ advice on finding your narrative, crafting fair and simple pricing models, avoiding unexpected fees that can lead to customer dissatisfaction, balancing usage-based pricing with fair value attribution (23:55) Looking into the future, impact of AI in refining pricing models, uncertainty and perceived security perceived by both sellers and buyers, especially for companies of different sizes, a balanced approach that combines variable and fixed elements to provide a strategic edge while ensuring fairness and transparency in pricing (32:15) Moving beyond guesswork and focusing on value capture and growth, advice for listeners to apply these insights in their pricing strategies, “be precise to get to the price”! (34:38) Favorite jam growing up in Stockholm 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 guessing out of pricing.   Resources:Niclas Lilja LinkedInYouniumMarcos Rivera LinkedInMarcos Rivera XPricing IOBook: Street Pricing

What if your SaaS bundling strategy could do more than just boost immediate sales?  Join me, Marcos Rivera, as I unravel the strategic art of product bundling today on Street Pricing. This episode isn't just about quick wins—it's about leveraging bundling to drive customer adoption and set the stage for future growth. Keeping bundles lean and focused is crucial. Overly complex bundles can lead to sales complications and downsells. Learn the power of strategic bundling, and you’ll learn how to craft combinations that meet a broader spectrum of customer needs. Major companies like McDonald's and HubSpot effectively use ‘soft bundles’ to offer attractive deals that target specific buyers without compromising value. With the less favored, but sometimes advantageous, hard bundles, it's critical to avoid pairing high-performing products with those that underperform. Tune in to transform your approach to product bundling and drive scalable success in the SaaS industry.In this episode:(00:00) Bundling, common misconceptions about bundling, strategic bundling, solving more problems for the customer and paving the way for future sales.(06:00) While bundles can drive growth, a bundle that’s too large or complex can actually backfire, creating friction during both the sales process and customer renewal periods.(08:29) How to combine products effectively to create bundles that add value for customers. Solving a sequence of problems, reducing context-switching for users, and creating economies of scale during implementation are key, all while being mindful not to overcomplicate things.(09:00) The most common types of bundles: ad hoc, framework, soft, and hard bundles. Marcos explains why ad hoc bundling is a mistake and outlines the benefits of using soft bundles, where products are sold together to solve complementary problems. He also shares a strategy for bundle pricing and emphasizes the importance of aligning product use cases and simplifying implementation.(12:00) Understanding customer use cases and ensuring that bundled products naturally complement each other to enhance value and support sustainable customer retention. Practical tips on avoiding common bundling mistakes and ensuring smooth implementation and onboarding processes.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 guessing out of pricing.   Resources: Marcos Rivera LinkedInMarcos Rivera XPricing IOBook: Street PricingEmail Street Pricing for a consultation

 Are you facing engineering bottlenecks with your pricing systems? Discover how early decisions can impact your SaaS scalability and what you can do about it.  Join me for a game-changing conversation with Fynn Glover, the visionary co-founder and CEO of Schematic. Fynn opens up about his entrepreneurial journey from lifestyle media to B2B SaaS, where he confronted the daunting challenges of scaling a company due to pricing pitfalls. His candid story reveals the pivotal lessons learned from instinct-driven pricing errors and how these hurdles led to the creation of Schematic, a solution dedicated to demystifying complex SaaS pricing structures.  We uncover the critical importance of understanding customer willingness to pay, especially when your business is in its infancy. Through Fynn's experiences and my own, we emphasize the power of engaging potential customers early on—at least 50 conversations deep—to truly gauge market interest. This strategic approach helps mitigate risks and unlocks a product's perceived value. Discover the essential questions that can reveal customer urgency and the external factors influencing purchasing decisions, equipping SaaS founders with actionable insights to build a robust pricing strategy from the outset.  Pricing systems in high-growth companies often face integration challenges, demanding foresight and strategic engineering decisions. We share firsthand experiences where seemingly simple pricing tweaks became major engineering undertakings, highlighting the need for adaptable systems that support swift, impactful business choices. Looking ahead, we explore the evolving landscape of SaaS pricing and packaging, the empowerment of B2B buyers, and the transformative influence of AI on software solutions.    In this episode:  (00:00) Intro and background of Fynn Glover, journey from founding a lifestyle media company to transitioning into B2B SaaS, emphasizing the critical missteps in instinct-driven pricing models that hindered growth and led to the creation of Schematic.  (0:08:19) The importance of understanding customer willingness to pay in the early stages of a business. Fynn advocates for extensive conversations with potential customers to validate market interest and reduce risk, thereby informing effective early-stage strategy development.  (0:15:00) Most common challenges high-growth companies face in managing pricing changes across various system stacks. Fynn illustrates how early engineering decisions can impede scalability and emphasizes the necessity of foresight to avoid costly setbacks, highlighting the often-neglected prioritization of monetization in product development.  (0:25:13) The evolving landscape of SaaS pricing and packaging standards, reflecting on the separation of concerns between business and engineering decisions. As B2B SaaS buyers demand greater flexibility, the role of AI in integrating cost implications into usage-based billing presents an open question for future software and business strategies.  (0:27:30) Reflections on the transformative role of AI in software, underscoring its dual nature as both a tool and a creator.   (0:33:44) Favorite jams - Mark Knopfler   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 a...

Why are 77% of companies hesitant to change their pricing despite inflationary pressures, and what can be done to overcome this fear?  Today I welcome special guest John Kotowski, co-founder of PricingSaaS for an enlightening conversation that unravels the intricate dance of strategic pricing, showcasing how it can be the linchpin driving your company's success. We dissect the challenges and rewards of implementing sophisticated pricing models without relying on a sales team, and examine how meticulous analysis uncovers churn and expansion opportunities. Even subtle pricing adjustments can yield significant revenue gains. Through stories of overcoming complexity and aligning product features with pricing paths, we lay out a pragmatic roadmap to achieving those sought-after revenue targets.  Turning to the future, we turn to the powerful yet complex realm of AI monetization. From companies like Notion and Algolia experimenting with add-ons to outcome-based pricing models, we explore the evolving landscape where AI features are not just enhancements but value propositions in themselves. With a keen focus on experimentation and infrastructure, we highlight the challenges and triumphs of monetizing AI, ensuring you walk away armed with insights to navigate the rapidly shifting sands of SaaS pricing.  In this episode:  (00:00) Intro and background of Pricing SaaS co-founder John Kotowski (04:05) Managing Complexity in Pricing Strategy - Managing product-led growth strategy, utilizing data analysis, and aligning features with upgrade paths. (10:26) Master pricing and monetization as a product leader, secure small wins, and progressively make bolder moves for business growth (15:50) Invest in tooling and infrastructure for successful monetization, exploring pricing strategies and trends, addressing challenges to capture value (27:14) Excessive discounts can lead to customer challenges. The importance of product stickiness (31:29) Monetizing AI Features in Pricing – About half of tech companies are experimenting with different pricing models for AI features, including add-ons and outcome-based pricing, while also creating new AI-driven products (46:09) Favorite jams - Nirvana as a 90s teen  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 guessing out of pricing.    Resources: John Kotowski LinkedIn PricingSaaS Pricing SaaS Benchmark Report Marcos Rivera LinkedIn Book: Street Pricing Email Street Pricing for a consultation