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

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?:  [email protected]

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

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:  https://www.amazon.com/Street-Pricing-Playlist-Leaders-SaaS/dp/1737528010
Want more information?:  [email protected]

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.

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/ 

Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret  https://a.co/d/5Kk7PMR 

Company: https://www.pricingio.com/about/ 

Marcos Rivera LinkedIn  https://www.linkedin.com/in/marcoslrivera/ 

Marcos Rivera X  https://x.com/PRICINGIO 

Pricing I/O  https://www.pricingio.com/ 

Book: Street Pricing  https://www.amazon.com/Street-Pricing-Playlist-Leaders-SaaS/dp/1737528010 

Email Street Pricing for a consultation [email protected] 

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: https://www.linkedin.com/in/keust/ 

Nishita Katere: https://www.linkedin.com/in/nishitakatere/ 

Jack LoGrasso: https://www.linkedin.com/in/jack-lograsso-686487173/ 

Brenden Murden: https://www.linkedin.com/in/brenden-murden/ 

Company: https://www.pricingio.com/about/ 

Marcos Rivera LinkedIn  

Marcos Rivera X  

Pricing I/O 
 
Book: Street Pricing 
 
Email Street Pricing for a consultation

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 RFP

Marcos Rivera LinkedIn

Marcos Rivera X

Pricing I/O

Book: Street Pricing

Email Street Pricing for a consultation 

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-cohen-8a8b4859/ 

Steve Inman LinkedIn: https://www.linkedin.com/in/inmansteven/ 

Mario Pereda LinkedIn: https://www.linkedin.com/in/mario-pereda/ 

Emily Sanz LinkedIn: https://www.linkedin.com/in/emily-sanz/ 

Amit Saraf LinkedIn: https://www.linkedin.com/in/amsaraf/ 

Marcos Rivera LinkedIn 

Marcos Rivera X 

Pricing I/O 

Book: Street Pricing 

Email Street Pricing for a consultation  

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 Metallica

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:

Eric Weiss LinkedIn

Chaos to Clarity

Marcos Rivera LinkedIn

Marcos Rivera X

Pricing IO

Book: Street Pricing

Email Street Pricing for a consultation 

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 LinkedIn
Younium
Marcos Rivera LinkedIn
Marcos Rivera X
Pricing IO
Book: Street Pricing
Email Street Pricing for a consultation