Monetizing SaaS

James D. Wilton, founder and managing partner of Monevate, brings over 20 years of experience in pricing strategy and monetization. His career began as a consultant at ZS Associates, followed by leading pricing at RELX and SBI. After three years at McKinsey, James launched Monevate, a consulting firm focused on helping tech startups, scale-ups, and fast-growing companies optimize their pricing strategies. In this conversation, James shares insights from his career and discusses the role of pricing strategy in modern business, the misconceptions surrounding it, and the challenges of implementing usage-based pricing models. He offers practical advice for companies looking to grow their pricing discipline and explores how AI is shaping the future of pricing. The discussion also highlights the importance of building community within the pricing space. Takeaways Pricing is often overlooked in modern MBA programs. Effective communication of pricing strategies is crucial. Discounting can lead to a culture of undervaluing products. Both qualitative and quantitative data are essential in pricing. Pricing strategy should be tailored to specific business situations. Companies often realize the need for pricing strategy at inflection points. Building a community around pricing is challenging but rewarding. Usage-based pricing presents unique operational challenges. Maintaining a logical record of deals is vital for pricing strategy. Integrity in consulting means providing honest advice, even when it's difficult. Chapters 00:00 Introduction and Background 01:43 Career Journey and Transition to Pricing 10:09 Key Learnings from Previous Roles 16:13 Founding Monovate and Building Community 22:34 The State of Pricing in B2B SaaS 29:29 Misconceptions in Pricing Strategy 39:40 Challenges of Usage-Based Pricing 48:44 Best Practices for Growing Companies 54:11 Formative Moments in Consulting

In this episode, we sit down with Jeff Escalante, now Engineering Director at Clerk. Jeff’s journey began in neuroscience, and over time, he transitioned into engineering leadership roles at incredible companies like HashiCorp, Vercel, and Clerk. He shares valuable lessons from his time at HashiCorp, reflecting on the challenges of managing rapid growth and the dual-focus needed to balance developer and enterprise requirements; discusses the complexities of building authentication systems and the strategic choices behind pricing and packaging at startups; and shares perspective to the infrastructure demands of scaling developer tools and speaks to the principles guiding Clerk’s focus on user experience. For those interested in product strategy, engineering leadership, or developer tools, this is a great conversation.

Takeaways:

Chapters

00:00 Jeff's Journey: From Neuroscience to Tech

05:57 Lessons from HashiCorp: Growth and Management Challenges

11:53 Navigating Pricing and Packaging at HashiCorp

17:46 The Duality of Developer and Enterprise Focus

22:59 Career Path Insights: The Evolution of Engineering Roles

30:05 Clerk: A New Chapter in Developer Tools

36:23 The Complexity of Authentication Systems

43:02 The Philosophy of selling to startups first and when to move to enterprise

50:38 Building for the Future: Infrastructure and Pricing

01:00:31 Lessons from Failure and Growth Mindset

Summary

In this episode of "Monetizing SaaS," we dive into the career journey of Kent Keirsey, founder and CEO of Invoke. With a background in economics and years of product leadership at high-profile tech companies like Gather and Greenlight, Kent shares invaluable insights into building and scaling successful products. He reflects on the critical role of culture, strategy, and communication in navigating rapid growth and managing teams effectively. Kent also explores the cutting edge of generative AI, from its technical evolution to its transformative potential in business. He offers practical advice on the importance of change management and champions in driving AI adoption within enterprises, and he discusses the complexities of pricing AI solutions—emphasizing the need for lasting client relationships. His reflections on building Invoke from an open-source project to a thriving business reveal a bold approach to risk and a mindset that values constant learning and an obsession with craft. Whether you're interested in the evolving landscape of AI, strategic growth in SaaS, pricing AI prdocts, or Kent’s entrepreneurial insights, this episode provides a wealth of knowledge and inspiration.

Takeaways

- Generative AI is transforming creative processes.

- Open-source projects can lead to significant business opportunities.

- Human involvement in AI is necessary for quality outcomes.

- Invoke aims to empower users with creative control over AI.

- The product serves a diverse range of users, from enterprises to individuals.

- AI deployment in enterprises is cautious and often starts with small pilots.

- The role of champions is crucial in advocating for AI solutions within organizations.

- Pricing strategies for AI solutions must evolve as the market and technology change.

- The cost of delivering AI solutions is decreasing, impacting pricing models.

Chapters

00:00 Kent's Journey Through Tech and Product Management

04:01 Lessons from Gather and Greenlight

09:56 Navigating Communication in Rapid Growth

13:11 Understanding Universe and Portfolio Management

15:02 The Emergence of Generative AI

19:59 Building Invoke: From Open Source to Business

23:50 Invoke's Product and Its Diverse User Base

29:10 The Evolution of AI Tools in Business

32:02 Navigating Change Management in Enterprises

35:20 The Role of Champions in AI Adoption

38:34 Pricing Strategies for AI Solutions

46:25 Building Long-Term Relationships with Clients

52:58 Embracing Risk and the Entrepreneurial Journey

Jules Boiteux, founder of Roast My Pricing Page, has a background in product management with roles at Marmelade App, Hull, Livestorm, and Trustpair. In this conversation, he shares his journey from product management to entrepreneurship and the lessons learned along the way. Jules discusses the role of pricing in B2B SaaS, the structure of an effective pricing page, and common mistakes, such as neglecting social proof and FAQs. He explains the differences between value-based and usage-based pricing models and highlights the ongoing development of pricing strategies in the market. Jules also explores future trends in monetization, including the influence of AI and the use of add-ons in pricing models. He emphasizes the importance of building community and sharing experiences to support personal and professional growth. Takeaways - The importance of a well-structured pricing page cannot be overstated. - Common mistakes on pricing pages include neglecting social proof and FAQs. - Value-based pricing often requires a different approach than usage-based pricing. - The market for pricing strategies is currently immature but evolving. - Pricing is a continuous process that requires regular testing and iteration. - Social proof is crucial for converting visitors on pricing pages. - The anatomy of a pricing page includes headlines, plans, and social proof. - Future trends in monetization will likely include more complex pricing models with add-ons. - Building community and sharing experiences is essential for personal and professional growth. Chapters 00:00 Introduction to Jules Boiteux and His Journey 02:31 Significant Experiences in Product Management 05:53 Founding Roast My Pricing Page 11:10 Understanding the Anatomy of a Pricing Page 19:39 Common Mistakes on Pricing Pages 22:36 The Importance of the Pricing Page 25:49 Value-Based vs. Usage-Based Pricing 31:02 The Influence of Internal Pricing Practices 36:02 Market Maturity in Pricing Strategies 39:31 Systems Governing Pricing and Packaging 42:19 Future Trends in Startup Monetization 45:27 Personal Insights and Community Building

In this episode, Miguel Oller, co-founder and CTO of Makeswift, shares his journey from an aspiring robotics PhD at Georgia Tech to becoming a successful SaaS entrepreneur & CTO. Miguel's career spans founding multiple companies like Shortweb and BLoveIt, before co-founding Makeswift, which was recently acquired by BigCommerce. In this conversation, Miguel dives into key insights from his early startup experiences, including the challenges of co-founder dynamics, navigating commercialization, and developing pricing strategies. He emphasizes the importance of trust and collaboration in building a strong team, the need for constant experimentation in product development & pricing, and the critical role of adaptability throughout the startup journey. Miguel also touches on the transformative impact of AI in shaping future products, and offers advice to aspiring founders—reminding them that strong team dynamics are far more important than just having a great idea. This episode is packed with valuable takeaways for anyone interested in entrepreneurship, technology, and startup success. Takeaways: - It's important to feel comfortable telling stories about your experience. -The startup journey is often a hyperbolic growth chamber. - Co-founder dynamics can make or break a startup. - Embracing unexpected roles can lead to valuable learning experiences. - Product market fit is a continuous journey, not a destination. - Building trust among co-founders is essential for long-term success. - The right technology at the right time can create opportunities. - Startups require a blend of passion and pragmatism. - Iterative processes help in building trust and resolving conflicts. - The journey of entrepreneurship is filled with highs and lows. You must learn how to have productive conflict. - Building trust is essential for effective collaboration. - Commercialization requires constant adaptation and experimentation. - Pricing strategies should align with the value provided to customers. - The journey of a founder is filled with learning opportunities. - Don't over index on the idea; focus on the team. - Learning should be a metric of success in startups. - AI will significantly change product development in the coming years. - Experimentation frameworks are crucial for navigating market changes. - The most formative experiences often come from the journey itself. Chapters 00:00 Introduction and Purpose of the Podcast 02:12 Miguel Oller's Journey: From Robotics to Startups 06:22 Early Startup Experiences: Shortweb and Blobbit 12:24 Transition to Makeswift: The Founding Story 20:08 The Evolution of Makeswift and Its Acquisition 24:20 Co-Founder Dynamics and Lessons Learned 28:00 Building Trust Through Collaboration 31:00 Lessons in Commercialization and Market Fit 34:03 The Importance of Experimentation Frameworks 39:03 Navigating Pricing Strategies 43:56 The Future of AI in Product Development 48:53 The Formative Journey of a Founder

Spyri Karasavva has had an incredible career in finance, SaaS, and pricing. She's been a financial analyst for a PE fund, worked in product & finance strategy for Stripe, was the first GTM hire at Stytch, is now the founder & CEO of Dealops. In this episode, Spyri shares her career journey and the importance of pricing in B2B sales. She discusses the challenges of deal pricing and the need for effective pricing strategies and guidance. She emphasizes the importance of collaboration between pricing, product, and sales teams and suggests that pricing strategy should be an integral part of the product development process. She also highlights the need for software solutions in pricing enablement, specifically during the quoting process, to enforce finance guidance and optimize deal economics. Takeaways - Pricing is a critical aspect of B2B sales, and non-standard deals often require careful decision-making on product inclusion, pricing, discounts, and payment terms. - Collaboration between pricing, product, and sales teams is essential for effective pricing strategies and guidance. - Pricing strategy should be integrated into the product development process, with the pricing team working closely with customers and users. - Deal pricing teams are best placed under the finance department to ensure alignment with company goals and protect gross margin and cash flow. - Software solutions, particularly during the quoting process, can optimize pricing enablement and provide custom pricing recommendations that align with finance guidance. - DealOps serves companies of all sizes, with a focus on larger companies with complex pricing models and thin margins. - DealOps is a good fit for industries facing price wars or commoditization. - DealOps aims to deliver at least 6 times ROI and capture around 15-18% of the value they create. - DealOps offers both revenue uplift and time efficiencies for sales teams. - Many companies lack good pricing performance data, which can hinder their ability to make informed pricing decisions. - The four-step process for pricing includes determining the right unit metric, setting the list price, deciding on discounts, and enforcing discounts. - Discounts should be aligned with customer segments and behavior incentives. - Monitoring and tracking pricing data is crucial for optimizing pricing strategies. Sound Bites "In the B2B world, it almost doesn't matter what price you have on your website. Most deals that actually get signed have some sort of custom price or are considered non-standard." "I think it's kind of crazy that nobody has really optimized the link between sales incentives, deal economics, and the company's bottom line." "The way to do B2B pricing enablement is through the quoting process. It's the only time that a rep cares a lot about pricing." "We need to deliver at least 6 times return on investment." "We reduce the time that it takes to price a deal from 30 minutes to 3-4 minutes." Chapters 00:00 Introduction and Background 02:49 The Importance of Pricing in B2B Sales 05:58 Collaboration between Pricing, Product, and Sales Teams 08:53 Integrating Pricing Strategy into Product Development 11:50 The Role of Deal Pricing Teams 15:01 Optimizing Pricing Enablement with Software Solutions 26:04 Serving Companies with Complex Pricing Models and Thin Margins 32:08 The Challenge of CRM and CPQ Setup 37:21 The Importance of Pricing Performance Data 42:24 The Four-Step Process for Pricing 47:57 Monitoring and Tracking Pricing Data keywords pricing, B2B sales, deal pricing, pricing strategy, collaboration, software solutions, quoting process, finance guidance, deal economics, pricing, software, companies, complex pricing models, thin margins, revenue uplift, time efficiencies

Gary Bailey, founder of the Talent Capitalist, is a monetization & pricing expert with a deep background in financial services, accounting, pricing, and AI. In this episode, Fynn and Gary discuss Gary's background in finance and what he learned from the electronification of finance. They go on to discuss the importance of monetization as a discipline. Gary shares his experience in valuing and pricing financial products, as well as the challenges of training young professionals in the industry. Bailey emphasizes the need for pricing education in business schools and the lack of ownership and accountability for monetization within organizations. Gary believes that pricing should live in finance, and that FP&A professionals have a massive opportunity to create value for their organizations should they lean into monetization as a concentrated function. Takeaways - Monetization should be treated as a discipline and taught in business schools to address the lack of pricing education. - Finance departments are well-positioned to own and drive monetization strategies within organizations. - The challenges of valuing and pricing financial products require a deep understanding of math and a focus on creating consistent valuation curves. - The rapid pace of change in the pricing landscape necessitates the development of pricing expertise and the recognition of pricing as a valuable discipline. - The lack of ownership and accountability for monetization within organizations leads to ambiguous pricing strategies and missed. opportunities. FP&A has the analytical skill set for monetization as well as the available time to lean into it. - The best argument for pricing to live in product is to treat pricing as a product itself, with a focus on making it beautiful, easy to onboard, and constantly experimenting and iterating. - The Talent Capitalist helps small businesses recruit for the job of a 'motivation architect' and trains existing employees in this discipline. - Monetization as a discipline involves creating value, measuring value, negotiating value capture, implementing systems to capture value, and determining the price point. - The future of monetization in the world of AI involves AI assisting individuals in configuring their own pricing based on their unique needs and value perception. - Understanding what people want is crucial in implementing big ideas and achieving incentive alignment. Sound Bites "I'm an accountant at heart, and accountants like certainty." "We had to develop a system which had hundreds of these features, like insurance, and each of those features had a value." "FP&A has the analytical skill set to be really skilled and strong around monetization, but they are the function in the business that has the most latency in their job to go pursue that discipline with the right amount of focus, the right amount of attention." "If you see pricing and billing and monetization as a product in itself, then the number one thing that says to do is to one, make it look beautiful, two, to onboard people onto it kind of easily. And, and then to constantly be experimenting and iterating." Chapters 00:00 Introduction and Background 02:03 The Thread that Unites Interests 06:29 Bringing Controls to the Banking World 10:30 Teaching Monetization as a Discipline 18:04 The Role of Finance in Monetization 23:31 The Lack of Pricing Education and Ownership 30:10 The Latency of FP&A in Pursuing Monetization 33:03 Recruiting for the Job of a 'Motivation Architect' 36:28 The Five Steps of Monetization as a Discipline 40:55 The Future of Monetization in the World of AI 58:57 Understanding What People Want: A Crucial Lesson keywords monetization, pricing, finance, valuation, financial products, training, ownership, accountability, FP&A, monetization, pricing, product, services, mental model, value-based pricing, performance-based pricing, AI, future, understanding, formative moment

Scott Mitchell, former CTO of SalesLoft, takes us through his career journey and shares hard-earned insights into the intricacies of pricing, packaging, and monetization in B2B SaaS. From the importance of culture and trust in scaling a company to the technical and strategic components of pricing, Scott offers a wealth of knowledge for any technical leader. He emphasizes the crucial role that a foundation of core values and a willingness to be vulnerable play in building trust within an executive team, especially when navigating complex changes.Scott dives into the architectural components of monetization, detailing how tools like Salesforce CPQ, billing systems, and custom provisioning come together to support a company's evolving pricing and packaging models. At SalesLoft, he spearheaded a major overhaul of their pricing and packaging strategy, transitioning from a rigid system to one where pricing changes became a metadata exercise—seamlessly decoupling pricing and packaging from the application code. For product & engineering leaders facing the challenge of aligning product and monetization roadmaps, Scott's experience offers invaluable guidance. He also shares his thoughts on the future, discussing how generative AI could impact software development. If you're a CTO looking to better understand the intersection of technology and monetization, and how to build an adaptable infrastructure that keeps pace with the market, this episode is a must-listen.

Takeaways

Sound Bites

Chapters

00:00 Introduction and Career Journey

06:23 Building Culture and Trust in Scaling a Company

13:35 The Challenges and Components of Pricing and Packaging in B2B SaaS

21:25 Architectural Components of Monetization in B2B SaaS

25:21 The Role of Core Values in Guiding Culture

27:19 The Need for a Provisioning System in Adapting to Changing Pricing and Packaging Models

27:27 Reworking Pricing and Packaging

30:13 Turning Pricing Changes into a Metadata Exercise

31:37 Repositioning as a Full Platform

34:08 Considering the Debt to Pay Off

37:37 Decoupling Pricing and Packaging from Application Code

43:12 Exploring the Impact of Generative AI

David Caughman has had a remarkable career in monetization, with experience in consulting at Simon Kucher, pricing strategy at Stripe, and now leading pricing at Docker. In this conversation, David & Fynn discuss the importance of pricing in software companies, where pricing should live, and what pricing leaders must excel at. David emphasizes the importance of understanding the strategic context of a company when developing pricing strategies and the multidisciplinary skillset required for pricing professionals, including data analysis, communication, and influencing. David believes that pricing should be treated as a product and should be aligned with the product roadmap. He also discusses the operational complexities of hybrid billing models and the need for customer control in AI pricing. At Simon Kucher, David learned the fundamentals. At Stripe, David learned the value of unbundling products and pricing them separately based on customer needs. And at Docker, he's learned about the operational complexities of evolving pricing & packaging as a company pursues a multi-product strategy. Takeaways - Pricing strategy should be developed within the strategic context of a company, considering customer segmentation, go-to-market strategy, and other components of the business strategy. - Implementing pricing recommendations in-house requires collaboration with various stakeholders and consideration of operational aspects. - Unbundling products and pricing them separately based on customer needs can drive incremental revenue. - Developing pricing models for new products and ensuring a seamless purchasing experience are crucial for growth. Pricing should be taken seriously and treated as a discipline that requires full-time focus. - Pricing professionals need a multidisciplinary skillset, including data analysis, communication, and influencing. - Pricing should be aligned with the product roadmap and treated as a product management function. - Hybrid billing models introduce operational complexities, but implementation complexity should not lead the decision-making process. - AI pricing should provide customer control and be aligned with the value customers are getting, not just the volume of output. - Involving implementation stakeholders in the pricing decision-making process helps build trust and ensures feasibility. Sound Bites "Pricing strategy is so much more than pricing. It touches all parts of a company's strategy." "You have to lead with value. You can't lead with anything else." "Going from free to paid is a great way to get yourself on the front page of Hacker News." "Pricing is multidisciplinary. It's hardcore data analysis, but at the same time, a very strategic qualitative component to it." "Wholeheartedly believe that pricing belongs in product." Chapters 00:00 Introduction and Career Journey 11:14 Foundational Learnings from Simon Kutcher 15:10 Lessons from Pricing at Stripe 23:57 Monetization Challenges at Docker 30:22 The Importance of Pricing 33:24 Aligning Pricing with the Product Roadmap 36:04 Operational Complexities of Hybrid Billing Models 49:41 Involving Implementation Stakeholders in Pricing Decisions Keywords monetization, pricing strategy, consulting, implementation, strategic context, unbundling, customer needs, purchasing experience, pricing, software companies, challenges, multidisciplinary skillset, product roadmap, hybrid billing, AI pricing, customer control, pricing committee, implementation stakeholders

Joe Ryan, VP of Product and Revenue Strategy at LaunchDarkly, shares his career journey and offers invaluable insights into sales, product leadership, and monetization. He emphasizes the role of curiosity in driving his career and the importance of mastering both sales and product knowledge. In this episode, Joe talked in depth about the complexities of aligning product and pricing roadmaps, discussing how a customer-centric approach is key to building a successful company. He breaks down the technical challenges of building a flexible billing infrastructure, managing product catalogs, and handling entitlements. Joe and Fynn explore the technical, organizational, and communication challenges of transitioning from a seat-based pricing model to a usage-based one, highlighting the necessity of staying close to customers and competitors while continuously adjusting pricing and packaging strategies. Joe emphasizes the critical role of the CEO, CRO, and CTO in driving and supporting these changes. He also shares his vision for the future of feature management, including the potential of AI to simplify software development and empower non-technical individuals. Joe's experience in product & revenue strategy has given him a deep understanding of business and customer value. What he's achieved in transitioning LaunchDarkly to usage-based billing is highly instructive for operators and founders. Listen to gain actionable insights from an industry expert who had a first row seat to the building of LaunchDarkly. Takeaways - Curiosity is a driving force in career growth and success. - Being able to sell and understand the product is a valuable skillset. - Aligning product roadmap and pricing roadmap is crucial for success. - Customer-centricity is key in building a successful company. - Building a flexible billing infrastructure requires careful planning and integration of multiple tools. - Managing product catalog and entitlements is a complex challenge. - Stay close to customers and competition to understand their needs and adjust pricing accordingly. - Pricing and packaging should be dynamic and constantly evaluated to maximize value for customers and the business. - The CEO plays a crucial role in setting pricing and packaging strategies and unblocking obstacles. The CRO and CTO are key stakeholders in driving and supporting pricing and packaging changes. - Feature management is an evolving category that helps organizations mitigate risk and optimize value delivery. - AI has the potential to simplify software development and empower non-technical individuals to solve problems. - Creating a product that is alive and responsive to market changes is essential for sustained innovation. - The future of pricing and packaging lies in understanding customer value and delivering it in a way that is simple and valuable. - The pricing role requires a deep understanding of business and customer perspectives. Sound Bites "Curiosity has been the driving force in my career." "A product manager is a salesperson." "If you lose sight of the customer, you don't really have a business." "I just had this mission to fix this for launch, directly fixes for the company, but really fix it for the customer. Pricing is a huge lever on the business and you got to get it right." Chapters 00:00 The Power of Curiosity in Career Growth 03:31 The Value of Selling and Understanding the Product 06:18 Aligning Product Roadmap and Pricing Roadmap 09:49 Building a Flexible Billing Infrastructure 22:19 Managing Product Catalog and Entitlements 24:36 Transitioning to a Usage-Based Pricing Model 26:19 Driving Change and Gaining Support 28:13 Identifying the Need for Change 30:27 Running a Successful Pricing Migration 32:30 The Role of Pricing and Packaging in an Organization 35:39 The CEO's Role in Pricing and Packaging 37:22 The CTO's Role in Pricing and Packaging 40:10 The Future of Feature Management and AI 43:56 Creating a Product that is Alive and Responsive

Rob Eanes, the co-founder & CTO of PingBoard and now VP Product at WorkLeap, shares his career journey and the vision for the combined companies. They aim to make work simpler by helping companies improve employee experience through better connections, communication, and engagement. Rob discusses the challenges of building and maintaining monetization infrastructure in the SaaS industry, emphasizing the need for clear data flow, considered architectural design of monetization infrastructure, and flexible pricing & packaging. He also highlights the importance of supporting customers with transparent pricing, packaging, and subscription management. Takeaways - WorkLeap aims to make work simpler by improving employee experience through better connections, communication, and engagement. - Building and maintaining monetization infrastructure in the SaaS industry is complex and requires clear data flow and considered tech stack, given pricing & packaging is governed by multiple systems. - Supporting customers with transparent pricing, packaging, and subscription management is crucial for a positive customer experience. - The challenges of monetization infrastructure affect businesses of all sizes, and it's important to be able to price & package in a way that's aligned with customer value, rather than dictated by your own systems' complexity. - The core components of modern monetization infrastructure include the application, go-to-market strategy, product catalog, support systems, and customer experience. Sound Bites "WorkLeap's mission is to make work simpler." "SaaS tools to help you manage your SaaS tools." "Expecting too much from your billing system." Chapters 00:00 Introduction and Career Journey 04:36 The Vision for WorkLeap 08:51 Transition from CTO to Product Leader 09:22 Building Trust between Product and Engineering 13:28 Market Inflections in B2B Software 19:30 Components of Modern Monetization Infrastructure 28:30 Mistakes in Building Monetization Infrastructure 33:27 Core Components of Monetization Infrastructure 37:38 Conclusion and Where to Learn More

Jon O'Bryan shares his journey from studying physics to co-founding property tech startups and now running Atlas.so. He discusses his experiences in academia, finance, and running an Airbnb business before co-founding Atlas. The vision for Atlas is to be the customer system of record, handling all customer information from support to sales. In five years, they aim to be the first point of intake for customers and provide insights for product development and customer success. In this conversation, Fynn & Jon discuss the challenges of entering the CRM market, the importance of finding a narrow wedge to gain initial traction, and the value of building a broad platform over time. They also touch on the lessons learned about monetization, including the need for simple and transparent pricing and criticality of establishing transparency with customers around billing & invoicing, especially for usage-based models. Takeaways - Jon O'Bryan's journey from academia to startups - The vision for Atlas as a customer system of record - The importance of customer support and insights for product development - The goal of turning potential customers into actual customers - Entering the CRM market requires finding a narrow wedge to gain initial traction.Building a broad platform over time provides more staying power but is harder to get in the door. - Monetization should have simple and transparent pricing to avoid churn risks.Independence and confidence in oneself are crucial for entrepreneurial success. - Lowering the bar for what is needed to be comfortable and happy in life allows for more risk-taking and pursuing big goals. Sound Bites "I met my co-founder Rahul and he had a lot of thoughts on what support should look like. Felt like it was too fragmented and I felt like from my experience at Pads, but had seen definitely like, this was an issue for us." "The vision for the business is to be essentially like your customer system of record. We want to be the first point of intake whenever a customer comes to your company and we hold on to their information until they leave." "In five years, I would like to be essentially like your customer system of record. We are the first point of intake whenever a customer comes to your company and we hold on to their information until they leave." "So attack the CRM market, enter with support is a good way to think about it." "The assumption in startup land for at least the last decade, decade and a half is that like more focused, more better, like the narrower, sharper, your, you know, the tip of your sword, the better." "If you can bring these silos together, there are like interesting interactions that you can only have if you are natively integrated on the same platform." Chapters 00:00 Introduction and Background 10:20 The Birth of Atlas 31:31 Entering the CRM Market 38:48 The Power of a Narrow Wedge 42:08 Building a Broad Platform 46:24 Lessons Learned about Monetization 54:46 The Impact of Independence on Entrepreneurship

Lindsay Trinkle, co-founder of Makeswift, shares her career journey and the vision behind the business. She discusses the importance of bringing monetization into product strategy early and the role of pricing in branding. Lindsay emphasizes the need to talk to customers and gather diverse opinions when it comes to pricing and packaging. She also highlights the challenges and complexities of monetization in B2B SaaS, including supporting multiple sales motions and billing models. Lindsay shares her formative experience of betting on herself and the company during a pivotal moment in her life. Takeaways - Bring monetization into product strategy early and consider pricing as part of your brand message and positioning. - Talk to customers and gather diverse opinions to understand their willingness to pay and the value they see in your product. - Iterate on pricing and packaging, and A/B test different pricing models to find the right fit for your target market. - Supporting multiple sales motions and billing models can be challenging in B2B SaaS, but it's important to find the right balance. - Bet on yourself and take risks, even when faced with overwhelming circumstances.

Steve, a software engineer and serial founder, shares his career journey and the lessons he has learned along the way. He discusses his current startup, Supered.io, which focuses on adoption and delivery of HubSpot services. Steve built at least two billing systems for Salesloft as they scaled from $0-$100M so is an expert on monetization infrastructure and understands firsthand the complexity of building and maintaining monetization systems. Steve shares his insights on pricing and packaging, the challenges of billing infrastructure, and the need for flexibility in adapting to customer demands. Takeaways - Monetization systems in SaaS companies are complex and require careful consideration of pricing, packaging, and billing infrastructure. - Flexibility is key in adapting to customer demands and evolving business models. - The future of software companies may involve multi-product suites and building companies with less funding. Sound Bites "I'm finally able to use a lot of those lessons that I picked up from all those years of basically prepping myself." "I think more and more companies want to buy larger suites of software that are easier to procure." Chapters 00:00 Steve's Career Journey 03:57 Superd: Adoption and Delivery of HubSpot Services 07:06 The Future of Software Companies 12:21 Building Trust and Alignment 16:21 Monetization in SaaS

Jen Ayers, COO of a private firm and experienced leader in information security and ops, shares her career journey and insights on building software companies, establishing trust between product and engineering teams, and the complexity of B2B SaaS monetization. She emphasizes the importance of delivering on commitments, understanding market behavior, and being flexible in pricing and packaging. Jen also discusses the challenges of achieving flexibility in engineering, the need for data-driven decision-making in pricing and packaging, and the formative experiences that shaped her professional growth. Takeaways - Career journeys are rarely linear, and it's important to embrace the winding path and seize opportunities in different industries and roles. - Building trust between product and engineering teams is crucial for success, and it can be achieved by delivering on commitments and open communication. - B2B SaaS companies face complexity in monetization due to different go-to-market motions, billing models, product evolution, and customer customization. - Flexibility is key in pricing and packaging, and companies should consider the impact on engineering, sales, and customers when making decisions. - Data-driven decision-making is essential in pricing and packaging, and companies should analyze customer usage and preferences to optimize their offerings. - Formative experiences, such as discovering new possibilities outside of a structured environment and building trust with visionary leaders, can shape professional growth. Sound Bites "Deliver on what you say you're going to do. Period. Hands down. That simple." Chapters 00:00 Jen Ayers' Interesting and Textured Career 03:19 Big Market Inflections in Building Software Companies 07:00 Building Trust Between Product and Engineering Teams 08:47 The Complexity of B2B SaaS Monetization 14:54 Data-Driven Decision-Making in Pricing and Packaging 18:51 Formative Experiences and Professional Growth

Tommy Noonan, a product leader with experience at companies like Full Story, Cypress, Interviewing.io, and Tropic, shares his career journey and insights on monetization in B2B SaaS. He discusses the challenges and complexities of building and supporting monetization infrastructure, emphasizing the importance of visibility, control, and leverage. Tommy also provides advice for product and engineering leaders, encouraging them to be bold in pricing and packaging decisions and to ensure that everyone in the company is aligned and has something to gain or lose from monetization changes. He highlights the formative experience of being at a rapidly growing company and learning from the best people. Takeaways - Building and supporting monetization infrastructure in B2B SaaS can be complex due to technical and operational challenges. - Visibility, control, and leverage are key components of a successful monetization system. - Product and engineering leaders should be bold in pricing and packaging decisions and ensure that everyone in the company is aligned and has something to gain or lose from monetization changes. - Being at a rapidly growing company provides valuable learning opportunities and personal growth. Sound Bites "Do things well thought out, but don't be scared to take big leaps." "Everyone at the company has something to gain or lose from pricing and packaging changes." "Being at a place that's growing rapidly is instrumental to personal growth." Chapters 00:00 Introduction and Career Journey 05:21 Monetization at Tropic 07:26 Curiosity and Trends in B2B Software 09:35 Framework for Thinking About Monetization 13:12 Complexity of Monetization in B2B SaaS 15:57 Systems and Tools for Monetization 23:35 Lessons for Product and Engineering Leaders 25:32 Formative Experience and Closing

In this conversation, Fynn and Pat Doran discuss the complexities of pricing and packaging in the software industry. Pat shares his insights from working with numerous SaaS companies and highlights the common mistakes made at different stages of growth. They also touch on the importance of data-driven decision-making and the need for a consistent pricing committee. Pat emphasizes the value of building a sound tech stack to support flexible control over pricing & packaging as a company evolves and and recommends quarterly evaluations to continually improve pricing strategies. Takeaways - Pricing and packaging in the software industry can be complex due to the many levers to pull and vectors of value to consider. - Early-stage companies often make the mistake of not focusing enough on pricing and undervaluing their products, leaving money on the table and conditioning buyers to expect more for less. - Growth-stage companies face challenges such as internal inertia, complexity, and the need to cut through the noise of multiple opinions. - Data-driven decision-making is crucial at this stage. - To continually improve pricing and packaging, companies should invest in a sound tech stack, establish a consistent pricing committee, and conduct quarterly evaluations. - Building a pricing committee and having a consistent meeting cadence can help ensure that pricing decisions are made with input from various stakeholders and reflect the value of the business. Sound Bites "If you're not waking up every day, cold sweats, thinking about AI and how it's going to disrupt your business or how you'll use it to disrupt someone else, you're probably shot." "If you don't have an eye towards profitability, you're also probably behind the eight ball." "The most common value metrics we see are per seat, per user, and usage levels such as number of gigs, videos, or projects." Chapters 00:00 Introduction and Recording 03:20 Market Inflections and Trends 06:12 Monetizing Software: Operational Complexity 09:00 Value Metrics and Pricing Models 10:45 Difference Between Pricing and Packaging 15:01 Common Mistakes in Pricing and Packaging 20:49 Mistakes and Misconceptions in Pricing 24:10 Closing Remarks and Contact Information

Rob Truesdell, CPO of Pangea Cloud, shares his journey in the tech industry and discusses the big market inflections in building software and security companies. He emphasizes the importance of delivering value quickly in the SaaS space and reducing time to value for developers. Rob also talks about the consumerization of enterprise software and the need to support multiple go-to-market motions, hybrid billing models, and selling multiple products. He explains the infrastructure and components Pangea built to support flexible pricing & packaging, highlighting their metering system, payments method, pricing tables, and integrations with downstream business systems (stripe for payments & hubspot for CRM). Takeaways - Delivering value quickly is crucial in the SaaS space, where attention spans are short and competition is high. - Enterprise software is being consumerized, and B2B companies need to support multiple go-to-market motions. - Supporting hybrid billing models and selling multiple products adds complexity to B2B SaaS businesses. - Building a flexible infrastructure for monetization enables control and scalability. - Over-communicating, building trust, and involving customers in the product development process are key to success. - Understanding customer needs and behaviors through communication and data analysis helps improve the product and customer experience. Sound Bites "Delivering value that packs a huge punch with your SaaS platform." "B2B software is being consumerized in the way it's purchased." "Supporting multiple go-to-market motions adds complexity to everything you're doing." Chapters 00:00 Rob's Journey in the Tech Industry 02:03 Delivering Value Quickly in the SaaS Space 04:21 Consumerization of Enterprise Software 06:36 Supporting Multiple Go-to-Market Motions 09:16 Removing Friction for Customers 12:19 Involving Customers in the Product Development Process 14:11 Complexity in Hybrid Billing and Selling Multiple Products 24:17 Control and Scalability in Packaging Offerings 26:20 Effort and Complexity of Building the Infrastructure

Tim Oshansky, a serial founder and technology leader, shares his career journey and experiences in various industries, including derivatives trading, construction technology, and restaurant technology. He discusses the importance of reducing friction in product, buying, and commercial aspects of a business. He also explores the complexity of pricing and packaging in B2B software and the challenges faced in implementing a flexible and scalable framework. The conversation explores the importance of data flow and integration in pricing and packaging management, as well as the use of feature flags and entitlements. It highlights the challenges of implementing standardized monetization infrastructure and the trade-offs between speed and correctness. The discussion also touches on the need for clear boundaries and decision-making processes in product offerings, as well as the separation of emotional reactions from rational decision-making. The conversation concludes with advice for product and engineering leaders at growth-stage SaaS companies. Takeaways - Tim has had a diverse career journey, working in derivatives trading, construction technology, and restaurant technology. - Reducing friction is crucial in product, buying, and commercial aspects of a business. - Pricing and packaging in B2B software can be complex due to the lack of structure and the need for short-term decisions. - Implementing a flexible and scalable framework for pricing and packaging is essential for long-term success. - Tight integration in data flow between Salesforce, product, and user analytics tools is essential for effective pricing and packaging management. - The use of feature flags and deployment flags allows for decoupling deployments from releases and enables more effective launch strategies. - Entitlements, both in terms of security and pricing, are important for managing user access and monetization. - Building a consolidated platform that combines billing, usage, product data, and CRM is crucial for leveraging data in all aspects of the business. - Early decision-making on product boundaries and a clear catalog of offerings can simplify implementation and avoid future challenges. - Separating emotional reactions from rational decision-making is critical in high-pressure situations, and having predefined processes and rules can help mitigate risks. - Product and engineering leaders should prioritize building a strong data infrastructure and incorporating relevant tools and products to support monetization efforts. Sound Bites "Software is eating the world." "The natural friction between product and engineering" "Opportunity in well-established markets" "Tight integration in data flow between Salesforce, product, and user analytics tools." "Using feature flags to decouple deployments from releases and partner with marketing and customer success." "Entitlements refer to what users can do or what customers have access to within a product." Chapters 00:00 Introduction and Career Journey 17:19 The Changing World of Business and Economy 22:39 Reducing Friction in Business 25:47 The Complexity of Pricing and Packaging 28:51 Data Flow and Integration 32:45 Entitlements and User Access 35:08 Building a Consolidated Platform 38:29 Speed vs Correctness in Implementation 43:37 Early Decision-making and Clear Boundaries 51:43 Separating Emotional Reactions 54:38 Advice for Product and Engineering Leaders

Thomas Sellers, Director of Strategic Pricing at UiPath, shares his journey in monetization and pricing. He discusses the challenges and considerations in pricing generative AI features and the importance of understanding the value and business impact of these features. Thomas also highlights the challenges faced by large organizations in evolving their monetization strategies and the need for building political capital and expertise in pricing. He explores the changes and inflections in the market, particularly in product-led motions, and the importance of developing monetization capabilities ahead of time. Monetization in B2B SaaS companies can be complex due to various factors such as supporting multiple sales motions, multiple products, and different price metrics. Pricing is not always the top priority for business leaders, who often focus on product and customer value. The challenge lies in prioritizing initiatives and aligning stakeholders to make decisions. Monetization complexity can also arise from commercial debt, where past decisions and technical limitations hinder pricing changes and tracking usage. Founders can use generative AI tools like ChatGPT to get initial pricing and packaging recommendations and seek advice from experts to avoid major pitfalls. Takeaways - Monetization is the process of tying together a company's offering, go-to-market strategy, profitability, and financial outlook. - Pricing generative AI features requires understanding the value and business impact they provide to customers. - Large organizations face challenges in aligning multiple stakeholders and making trade-offs in pricing decisions. - Early-stage companies should dedicate time to pricing, document their decisions, and iterate based on feedback. - Changes in the market, such as the tightening of funds, present opportunities for developing monetization capabilities ahead of time. - Monetization in B2B SaaS companies can be complex due to multiple sales motions, products, and price metrics. - Pricing is not always the top priority for business leaders, who often focus on product and customer value. - Aligning stakeholders and making prioritization decisions is crucial in monetization. - Commercial debt, caused by past decisions and technical limitations, can hinder pricing changes and tracking usage. - Generative AI tools like ChatGPT can provide initial pricing recommendations, and seeking advice from experts can help founders avoid major pitfalls. Sound Bites "Pricing generative AI features: value and business impact" "Challenges in pricing for large organizations" "Is it fair to say that part of what makes monetization so complex, at least in enterprise, is how you prioritize effectively material changes to the customer experience?" "Organizational alignment becomes, I think the name of the game. If you can do that well and do it consistently over time, then you basically increase a large company's ability to execute and execute quickly." Chapters 00:00 The Journey in Monetization and Pricing 08:59 Challenges in Pricing Generative AI Features 15:39 Navigating Pricing in Large Organizations 19:41 Changes and Inflections in the Market 23:17 The Complexity of Monetization in B2B SaaS Companies 26:23 Prioritizing Initiatives and Aligning Stakeholders in Monetization 28:05 Organizational Alignment and Execution in Monetization 32:23 The Role of Engineering in Monetization 35:37 Lessons Learned from a Failed Product and the Importance of Failure

Fazal Gupta is the co-founder of Logik.io. He began his career in India, where he studied computer science and worked as a developer. Gupta then moved to the US where he joined BigMachines, which in many ways created the CPQ (Configure, Price, Quote) category. Over the course of his journey, he transitioned from software engineering to product, eventually taking on product leadership roles at Oracle and Workday before co-founding Logik in 2021. What We Covered in the Interview - Fazal's career journey from India to the US and his roles at Big Machines, Oracle, and Workday. - The founding of Logik and the insights behind the business. - Significant trends in enterprise SaaS, including AI integration and changing buyer expectations. - The operational complexities of supporting diverse customer needs and monetization strategies. - The importance of flexible pricing and packaging models in today's SaaS market. - Architecting for flexibility with cloud-native solutions in the B2B landscape.

In this conversation, Fynn Glover interviews Aubrey Rhodes, CTO of Workful and former engineering leader for Calendly & Mailchimp, about his professional journey and his experience with monetization and billing in SaaS companies. They discuss the importance of having a flexible architecture for monetization, the challenges of coupling business logic with the application code, and the need for a unified product catalog. They also highlight the impact of technical and commercial debt on engineering teams and provide advice for product engineering leaders to avoid these challenges. Takeaways - Having a flexible architecture for monetization is crucial for SaaS companies to adapt to changing pricing and packaging needs. - Coupling business logic with the application code can lead to technical and commercial debt, causing engineering teams to become bottlenecks for opportunities. - A unified product catalog is essential to avoid multiple sources of truth and simplify the management of products, entitlements, and pricing. - Technical debt refers to the opportunity costs incurred by needed engineering work, while commercial debt refers to the costs of maintaining multiple product catalogs and systems. - Product engineering leaders should consider buying solutions for billing and monetization instead of building them from scratch, and focus on setting up flexibility from the start to avoid future engineering work. - The trend of doing more with less and making software more delightful and easy to use is making it possible for small companies to build impactful SaaS products. Sound Bites "One of the important things to avoid is just feeling like your product is different. For the most part with SaaS applications, there's very few cases where you're going to want to do something with billing that's different than most other companies." "As much as you can do to set yourself up in the future to not have to spend engineering time on billing and pricing in the future. That's really valuable." Chapters 00:00 Introduction and Professional Journey 02:11 Transitioning from Calendly to Workful 05:16 Lessons Learned from Monetization and Billing at Calendly 08:52 The Complexity of Production Engineering in Monetization 11:26 The Role of Entitlements and Product Catalog in Monetization 20:24 Key Systems Governing Monetization and Pricing 24:39 The Evolution of Services in Monetization at Calendly 28:19 The Root Cause of Complexity in Monetization 31:51 Defining Technical and Commercial Debt 33:35 Defining the Product Catalog and Its Importance 36:45 Advice for Product Engineering Leaders 39:45 The Trend of Doing More with Less in SaaS keywords monetization, billing, SaaS, technical debt, commercial debt, product catalog, entitlements, architecture

Ulrik Lehrskov-Schmidt, a global expert in B2B SaaS pricing and packaging, shares his journey and insights on pricing and packaging in the B2B SaaS industry. He emphasizes the importance of pricing and packaging as a lever for growth and the need for companies to work on it rather than settling for good enough. Ulrik discusses common mistakes made by founders and CEOs, such as overcomplicating pricing and letting sales drive strategy. He also highlights the role of data in building a great pricing muscle and the need for a process to turn data into actionable insights. The conversation covers various topics related to pricing and monetization in B2B SaaS. Fynn & Ulrik discuss the importance of solving for risk and reverse engineering pricing decisions. They also explore the limitations of feature-based analysis and the role of intuition in pricing. The conversation covers negotiation strategies, emphasizing the need for win-win outcomes and the importance of having a strong alternative. They also discuss the operational challenges of pricing and packaging in software, including the impact of commercial debt and complexity. They highlight the need to stop incurring new debt and clean up existing commercial debt to enable value creation. takeaways - Pricing and packaging is a key lever for growth in the B2B SaaS industry. - Many companies settle for good enough pricing and packaging instead of maximizing its potential. - Common mistakes include overcomplicating pricing, letting sales drive it, and not working on pricing and packaging. - Data is important, but companies should focus on having a process to turn data into actionable insights. - Alignment between product and sales is crucial for effective pricing and packaging. - A pricing committee, led by the CEO, can help ensure ongoing review and decision-making on pricing and packaging. Solve for risk and reverse engineer pricing decisions - Consider the limitations of feature-based analysis and the role of intuition in pricing - Negotiate for win-win outcomes and have a strong alternative - Stop incurring new commercial debt and clean up existing debt to enable value creation Sound Bites "Pricing and packaging is almost as important as the product itself." "Many companies settle for good enough pricing and packaging instead of maximizing its potential." "The most common mistake is to not work on pricing and packaging." "You sort of work backwards" "It's often better to have avoided the feature level discovery because you've exited a conversation predicated on value and gotten yourself into a place that probably requires a lot of discounting because you're competing on features." "The feature-based analysis that you sometimes do with Conjoint and MaxDiff and all this, the whole utility analysis on a feature level is largely academic." Chapters 00:00 Introduction and Background 08:19 Key Learnings in Pricing and Packaging 14:24 Common Mistakes in B2B SaaS Pricing and Packaging 19:15 The Role of Data in Pricing and Packaging 23:12 Ownership and Alignment in Pricing and Packaging 27:32 The Role of a Pricing Committee 34:32 Solving for Risk and Reverse Engineering Pricing Decisions 36:41 The Limitations of Feature-Based Analysis and the Role of Intuition in Pricing 42:37 Negotiating for Win-Win Outcomes and Having a Strong Alternative 52:11 The Challenges of Commercial Debt and Complexity in Pricing and Packaging 01:06:09 Changing the Pricing Model to Unlock Additional Value keywords B2B SaaS pricing, packaging, growth, mistakes, data, process, pricing, monetization, B2B SaaS, risk, reverse engineering, feature-based analysis, intuition, negotiation, win-win, alternative, commercial debt, complexity, value creation, pricing model

Jon Sadow, co-founder of Scoop, shares his journey from being a product manager at Google to building a successful carpooling and commuting platform. However, when COVID hit, their business took a major hit. They pivoted to focus on productivity and helping companies manage hybrid work. They built a data product called the Flex Index, which provides benchmarks and insights for companies to make informed decisions about their office spaces. They monetize the product through subscriptions and plan to offer additional tools and functionality in the future. Companies often struggle to evolve their pricing and packaging flexibly due to a combination of factors. One reason is the perception that pricing is static and doesn't need to change as much as other aspects of the business. Another challenge is the technical infrastructure behind pricing, particularly billing systems, which are complex and often under-resourced. Complexity in pricing leads to complexity in the system, making it harder to adapt and change. To overcome these challenges, it's important to align the product roadmap with pricing and packaging initiatives, prioritize simplicity in pricing, and build a flexible architecture that allows for future changes. Takeaways - Jon Sadow's journey from product manager at Google to co-founder of Scoop - The impact of COVID on Scoop and their pivot to productivity and hybrid work - The development of the Flex Index as a data product for office benchmarks - Monetization through subscriptions and plans for additional tools and functionality - The challenges and importance of pricing and packaging in a marketplace product - Pricing should not be treated as a static element of the business, but rather should evolve along with the product and go-to-market strategies. - Complexity in pricing leads to complexity in the technical infrastructure, particularly billing systems, making it harder to adapt and change. - To overcome these challenges, it's important to align the product roadmap with pricing and packaging initiatives, prioritize simplicity in pricing, and build a flexible architecture that allows for future changes. - The relationship between product and go-to-market teams is crucial in determining the success of pricing and packaging strategies, and both teams should work in harmony to communicate value and understand customer perceptions. Sound Bites "The idea that pricing is static while your product is changing is pretty illogical when you think about it." Chapters 00:00 Jon Sadow's Journey as a Founder 02:39 Pivoting to Productivity and Hybrid Work 05:33 Introducing the Flex Index 09:25 Understanding What Other Companies Are Doing 17:08 Monetizing the Flex Index 23:01 The Challenges of Pricing and Packaging 25:05 The Challenge of Evolving Pricing and Packaging 29:50 Aligning Product Roadmap with Pricing and Packaging 34:12 The Complexity of Billing Systems and Technical Infrastructure 37:28 Building a Flexible Architecture for Pricing and Packaging 41:23 The Relationship Between Product and Monetization 44:18 The Importance of Simplicity in Pricing 45:45 The Future of Pricing and Billing Systems 48:36 The Formative Experience of Navigating Pricing Challenges Keywords Jon Sadow, Scoop, carpooling, commuting, COVID, hybrid work, productivity, Flex Index, data product, benchmarks, insights, subscriptions, pricing, packaging, marketplace, pricing, packaging, evolution, flexibility, billing systems, complexity, product roadmap, alignment, simplicity, architecture

Daniel Hellerman, co-founder and CPO of Saleo, shares his journey from developing iPhone apps to building a platform for personalized demos. He discusses the importance of user experience and hyper-personalization in B2B software. Saleo offers a unique choice in the demo software market by providing truly live demos that replicate the needs of prospects. The company has experienced rapid growth, particularly in the enterprise market. Hellerman also explores the future of AI and machine learning in transforming enterprise software and predicts a shift towards performance-based pricing. The conversation explores the topics of pricing, packaging, and monetization in B2B SaaS companies. Dan shares his insights and experiences from his time at Terminus and his current role at Saleo. He discusses the importance of aligning pricing with customer value and retention, as well as the need for personalized pricing packages. He also talks about the role of entitlements in monetization and the challenges of managing them. Additionally, he emphasizes the importance of getting new features in the hands of customers and avoiding the mistake of gating them or charging for them, before they have proven to drive adoption. Takeaways - User experience and hyper-personalization are crucial in B2B software. - Saleo offers truly live demos that replicate the needs of prospects. - The company has experienced rapid growth in the enterprise market. - AI and machine learning will transform enterprise software and may lead to performance-based pricing. - Align pricing with customer value and retention to increase contract size and net revenue retention. - Personalize pricing packages based on customer needs and roles. - Manage entitlements effectively to ensure customers have access to the right features. - Get new features in the hands of customers to create value and drive adoption. - Avoid the mistake of not creating value for customers with new features. Sound Bites "I love when people say this is really cool." "The market was the inverse of what I expected." "If you don't have personalized packages, you sort of failed at your own mantra from day one." "What are people going to pay more for, substantially more, to increase their size of their contract each year?" Chapters 00:00 Introduction and Going Offline 06:03 The Thread of User Experience and Hyper-Personalization 09:25 Salio's Unique Offering in the Demo Software Market 11:40 Focus on Scaling and Implementation 13:24 Surprises and Lessons Learned 16:23 The Reverse Order of Enterprise Market Success 19:25 Inflections and Curiosity for the Next 10 Years 22:22 AI and Machine Learning in Enterprise Software 25:35 Pricing and Packaging Challenges 29:09 Personalized Pricing Packages for Customer Needs 32:35 Creating Value with New Features 34:48 Avoiding the Mistake of Not Creating Value Keywords product development, personalized demos, B2B software, live demos, enterprise market, AI, machine learning, performance-based pricing, pricing, packaging, monetization, B2B SaaS, customer value, retention, personalized pricing, entitlements, features, value creation

Harker Roslin shares his career journey from teaching philosophy to working in tech and product leadership roles. He discusses his current role at HubSpot and the focus on ease of use and time to value. Harker also talks about the importance of pricing and packaging in B2B SaaS and the need for intentional decision-making and trade-offs. He emphasizes the alignment between the pricing roadmap and the product roadmap and the impact of pricing changes on the product development process. The conversation explores the challenges of implementing and managing monetization in B2B SaaS companies. The main theme revolves around the concept of rigid infrastructure and the impact it has on pricing and packaging. The conversation highlights the importance of choosing flexible tools and making foundational decisions that allow for future scalability. It also emphasizes the need for clear communication and documentation in order to effectively manage pricing and packaging. The conversation provides insights into the complexities of handling customer exceptions, dealing with legacy customer sets, and the potential technical debt that can arise from pricing decisions. Takeaways - Harker Roslin's career journey involved transitioning from teaching philosophy to working in tech and product leadership roles. - HubSpot's focus on ease of use and time to value attracted Harker to the company. - Pricing and packaging in B2B SaaS require intentional decision-making and trade-offs. - The pricing roadmap and the product roadmap should be aligned in a product-led growth organization. - Changes in pricing and packaging can impact the product development process and require flexibility and adaptability. - Choose flexible tools that can accommodate different pricing scenariosMake foundational decisions that allow for future scalability. - Clear communication and documentation are crucial for managing pricing and packaging - Handling customer exceptions and legacy customer sets can be complex and time-consuming. - Consider the potential technical debt that may arise from pricing decisions. Sound Bites "What I hope to do with this podcast and conversations like this is try to propose an architecture that can be more of a standard and a pattern for people." Chapters 00:00 Harker Roslin's Career Journey 03:39 HubSpot's Focus on Ease of Use and Time to Value 08:06 Navigating Pricing and Packaging in B2B SaaS 15:22 Aligning the Pricing Roadmap and the Product Roadmap 19:16 The Impact of Pricing Changes on Product Development 33:25 The Challenges of Rigid Infrastructure 38:01 Proposing a Standard Architecture for Monetization 44:41 Reinventing the Wheel in Monetization 50:24 The Complexity of Pricing Changes 54:18 Best Practices for Effective Monetization 57:03 Formative Experience: Taking Self-Service Pricing from Zero to Four Keywords career journey, tech, product leadership, HubSpot, ease of use, time to value, pricing and packaging, B2B SaaS, decision-making, trade-offs, roadmap, product development, monetization, pricing, packaging, B2B SaaS, rigid infrastructure, tools, flexibility, technical debt, customer exceptions, legacy customers

Ryan Johnson, CPO of CallRail, shares his journey in product management and the evolution of CallRail as a lead intelligence company. He discusses the company's focus on conversational intelligence and the use of AI to summarize phone calls, analyze sentiment, and generate follow-up emails.

Ryan also explores the potential disruption in the search industry and the challenges of pricing and packaging in a complex SaaS business. He highlights the cross-functional team at CallRail that handles billing, pricing, and packaging, as well as the systems involved, such as Zora and NetSuite.

The conversation explores the challenges of building and managing a monetization system for B2B SaaS companies. It discusses the lack of standardization and the tendency for companies to reinvent the wheel when it comes to monetization. The conversation emphasizes the importance of early investment in standardized solutions and the need to focus on core product development rather than building internal billing and monetization systems. It also touches on the complexity of pricing models and the impact of AI on cost of goods sold (COGS). The conversation concludes with advice for early-stage companies on preserving agility and flexibility in monetization.

Takeaways

- CallRail has evolved from a call tracking and analytics company to a lead intelligence company with a focus on conversation intelligence and AI.

- The search industry is facing potential disruption, and companies like Google may need to adapt to new technologies and approaches.

- Pricing and packaging in a complex SaaS business like CallRail can be challenging, requiring a cross-functional team and coordination with finance and engineering.

- Systems like Zora and NetSuite play a crucial role in governing pricing, packaging, and billing in a SaaS company. Building and managing a monetization system for B2B SaaS companies can be challenging and often involves reinventing the wheel.

- Early investment in standardized solutions can help companies avoid the need for extensive internal development and allow them to focus on core product development.

- Pricing models in B2B SaaS can be complex, especially when there is a usage component involved.

- The impact of AI on cost of goods sold (COGS) is an important consideration for companies developing AI-powered products.

- Preserving agility and flexibility in monetization is crucial for early-stage companies, and working with experts in the field can be beneficial.

Sound Bites

"Over the past six years, CallRail has been focusing on the conversation that happens during phone calls, leveraging AI to summarize, analyze sentiment, and generate follow-up emails."

"The search industry is facing real threats, and companies like Google may need to adapt to new technologies and approaches."

"Pricing and packaging in a complex SaaS business like CallRail can be challenging, especially as the company grows and introduces new products and promotions."

"You're building your app and so certainly not as easy as being able to utilize other software to help manage that for you."

"Product and engineering generally have to go build monetization and B2B SaaS. And it feels like they generally don't have a standard or a pattern that they can refer to."

Chapters

00:00 Introduction and Ryan Johnson's Journey

04:58 The Evolution of CallRail: From Call Tracking to Lead Intelligence

08:03 The Potential Disruption in the Search Industry

16:29 Challenges of Pricing and Packaging in a Complex SaaS Business

25:15 The Role of Systems in Governing Pricing and Billing

29:19 The Need for Standardization

31:46 The Complexity of Pricing Models

34:58 The Impact of AI on COGS

43:16 Preserving Agility and Flexibility

Keywords

Ryan Johnson, CallRail, product management, conversation intelligence, AI, lead intelligence, search industry, pricing, packaging, SaaS, billing, Zora, NetSuite, monetization, B2B SaaS, standardization, internal development, pricing models, cost of goods sold (COGS), agility, flexibility

Farhan Manjiyani, Senior Manager of Pricing and Commercialization at Grafana Labs, discusses the company's approach to pricing and packaging. He highlights the importance of being long-term greedy and focusing on value-based pricing. The commercialization team at Grafana Labs is responsible for deal strategy, pricing strategy, and competitive intelligence.

Farhan shares examples of how the team supports each pillar, including working with sales reps on deal negotiations and optimizing usage for customers. He also discusses the incredible growth and success of Grafana Labs and the unique culture that supports long-term thinking.

Farhan discusses the importance of customer conversations in pricing decisions, debunks misconceptions about pricing, and emphasizes the need for continuous pricing experimentation and the focus on the unit of measure rather than just the price point. He also shares best practices for pricing and monetization for early-stage companies and the importance of involving product and engineering teams in the pricing strategy. He explores the challenges of complex billing systems and suggests the need for an independent layer to support flexible monetization. Farhan also discusses future trends in pricing, such as outcome-based pricing and the impact of commoditization on differentiation.

Takeaways

- Grafana Labs takes a long-term greedy approach to pricing and packaging, focusing on value-based pricing and maintaining a strong open-source community.

- The commercialization team at Grafana Labs is responsible for deal strategy, pricing strategy, and competitive intelligence.

- The team works closely with sales reps to develop creative pricing strategies and defend value in deal negotiations.

- Grafana Labs has experienced significant growth, with over 2000 paying customers and a million active instances of Grafana in the community.

- The company's success is attributed to its unique culture of long-term thinking and commitment to customer-centricity. Customer conversations are crucial in pricing decisions and should be prioritized over internal opinions.

- Pricing is not a one-time exercise; it requires continuous experimentation and pressure testing with customers.

- Early-stage companies should have a path to monetization from the beginning and regularly revisit and debate their pricing strategy.

- Product and engineering teams play a critical role in supporting the pricing strategy and should be involved in pricing discussions.

- Complex billing systems can hinder pricing flexibility, and there is a need for an independent layer to support agile monetization.

- Future trends in pricing include outcome-based pricing and the need for predictability in buying decisions.

- Commoditization of certain aspects of SaaS products may require differentiation through packaging and pricing models.

- Formative moments in Farhan's career include taking over the competitive team at Grafana Labs and building out a competitive program for a global company.

Sound Bites

"We don't want to make short-term trade-offs if it means anything in the long run."

"The one mistake people make is in deciding their pricing, they don't realize that they're actually just debating their own opinion."

"It's all about the unit of measure. Because the unit of measure is much harder to change."

Chapters

00:00 Introduction and Initial Challenges

03:46 The Role of the Commercialization Team

07:40 Value-Based Pricing at Grafana Labs

10:38 Monetization Tutorial for Sales Reps

11:09 Supporting Deal Operations

14:22 The Importance of Long-Term Thinking

17:18 The Growth and Success of Grafana Labs

24:15 Challenges in Implementing Long-Term Thinking

27:20 The Importance of Customer Conversations in Pricing Decisions

28:48 Continuous Experimentation and Pressure Testing in Pricing

32:50 Best Practices for Pricing and Monetization in Early-Stage Companies

36:38 Involving Product and Engineering Teams in Pricing Strategy

43:26 Challenges of Complex Billing Systems and the Need for an Independent Layer

50:22 Future Trends in Pricing: Outcome-Based Pricing and Differentiation

54:02 Formative Moments in Farhan's Career: Taking Over the Competitive Team

Kayvan Dastgheib shares his career journey in revenue operations and highlights the importance of building strong foundations in sales, customer success, and marketing.

He emphasizes the role of revenue operations in aligning different departments and ensuring scalable infrastructure and discusses the significance of gross revenue retention and pipeline conversion in driving growth.

The conversation explores the challenges organizations face in pricing and packaging their products and the role of systems and infrastructure in implementing effective monetization strategies.

The discussion also delves into the concept of tech debt and its impact on monetization strategy.

The conversation concludes with a discussion on the architectural components necessary for a cohesive monetization infrastructure, including entitlements, company profiles, and product catalogs.

Takeaways

- Revenue operations plays a crucial role in aligning sales, customer success, and marketing departments and building scalable infrastructure.

- Gross revenue retention and pipeline conversion are key focus areas for revenue operations leaders.

- The AI trend in SaaS should be approached with caution, and organizations should prioritize building strong product and engineering teams.

- Monetization in B2B SaaS is complex and requires a sophisticated understanding of the customer journey and pricing strategies.

- Organizations often struggle with pricing and packaging their products due to a lack of clarity in their monetization strategies.

- Engineering plays a critical role in implementing effective pricing and packaging strategies.

- Tech debt can hinder go-to-market efforts and limit business agility.

- A cohesive monetization infrastructure requires architectural components such as entitlements, company profiles, and product catalogs.

Sound Bites 

"Most organizations don't know what they're actually trying to accomplish with pricing and packaging."

"There's the strategy question, which is what should the price be? How should we package this product? But then there's the actual, like, how do we action that strategy side of the equation?"

"If you you're trying to introduce an enterprise solution, but you don't have the functionality parsed out to give yourself an enterprise value problem, you're not enterprise ready."

Chapters

00:00 Introduction and Career Journey

05:11 Defining Revenue Operations

10:05 Focus on Gross Revenue Retention

15:03 Prioritizing Pipeline Conversion

22:45 Complexities of Monetization in B2B SaaS

25:55 The Challenges of Pricing and Packaging

30:19 The Role of Engineering in Monetization Strategies

36:29 The Impact of Tech Debt on Go-to-Market Efforts

40:57 Architectural Components for a Cohesive Monetization Infrastructure

Keywords

career journey, revenue operations, sales, customer success, marketing, infrastructure, gross revenue retention, pipeline conversion, AI, monetization, pricing, packaging, monetization strategies, systems challenges, customer value, engineering involvement, tech debt, go-to-market, architectural components, entitlements, company profiles, product catalogs

Brian Rinaldi, a software developer advocate who spent the last two years at LaunchDarkly and who recently joined LocalStack, shares his journey in the tech industry and discusses the evolution of developer advocacy & the opportunity to extend feature flags beyond rollout and into entitlements.

He emphasizes the importance of content and community in developer advocacy programs and provides insights on how startups can structure their programs effectively. Brian also discusses the concept of entitlements in SaaS and the role of feature flags in managing entitlements. He highlights the power of feature management in simplifying entitlement setups and enabling business agility.

Keywords

developer advocacy, content, community, startups, entitlements, feature flags, feature management, SaaS

Takeaways

Developer advocacy has evolved from simply evangelizing to focusing on teaching and enabling developers.

Startups should prioritize content creation and community building in their developer advocacy programs.

Feature flags can be used to manage entitlements in SaaS, providing flexibility and simplifying the process.

Feature management is at the root of modern monetization complexity in B2B SaaS.

Being solution-oriented and presenting alternatives is crucial in problem-solving and collaboration.

Chapters

00:00 - Introduction and Brian's Journey

02:07 - The Evolution of Developer Advocacy

04:11 - Building Effective Developer Advocacy Programs

06:17 - Simplifying Entitlements with Feature Flags

08:30 - The Power of Feature Management

23:18 - Being Solution-Oriented: A Key Lesson for Career Success

25:37 - Conclusion and Brian's Contact Information

Justin Gagnon is a growth engineering leader at Calendly. In this episode of Monetizing SaaS, he discusses the complexity of monetization in B2B SaaS businesses.

He emphasizes the importance of treating monetization as a first-class citizen from the beginning and not as an afterthought. Gagnon highlights the need for a clear pricing and packaging strategy, as well as a robust entitlements system. He acknowledges the challenge of maintaining legacy pricing models while introducing new products and features. Gagnon also discusses the role of production engineering in building and maintaining monetization infrastructure.

The conversation explores the importance of monetization infrastructure and the role of entitlements and feature flags in achieving agility. It emphasizes the need for a central point of truth for entitlements and the benefits of extracting services for agility, such as metering, entitlements, product catalog, and subscriptions. The discussion also touches on the significance of a well-designed product catalog and the challenges of maintaining flexibility and transparency in B2B software.

Takeaways

Sound Bites

"Monetization should be a first class citizen as early as humanly possible."

"Monetization is not really one of those things that even the most adept developer can build a good strategy by themselves in a vacuum."

"Monetization needs to be thought about from day one."

"I'm not worried about entitlements. So I'm pretty much putting everything behind if else statements, which is terrible. But that's what I'm gonna do because we need to get out there." "When using feature flags as interface, you'll get a Boolean flag back."

"Monetization is not necessarily a science. There's a little bit of gut feeling that goes into it."

Chapters

0:00 Introduction and Background

04:42 Justin's Role at Calendly and Focus on Growth

07:00 The Complexity of Monetization at Calendly

10:19 The Role of Entitlements in Monetization

14:26 The Need for a Standard or Pattern in Monetization Infrastructure

29:59 The Role of Entitlements and Feature Flags

35:35 The Importance of a Well-Designed Product Catalog

38:15 Embracing Uncertainty in Monetization

44:48 Prioritizing Personal Work-Life Balance

Keywords monetization, B2B SaaS, pricing, packaging, entitlements, complexity, production engineering, monetization infrastructure, entitlements, feature flags, agility, central point of truth, product catalog, B2B software, uncertainty, work-life balance

Bill Tarr is a solutions architect for AWS. In this episode of Monetizing SaaS, he discusses his career journey in software development and the role of the SaaS Factory team at AWS. He emphasizes the importance of understanding costs, both cost per tenant and cost per feature, especially in the wake of generative AI. Bill highlights the significance of feature flags in managing and packaging features, as well as the challenges of entitlements in supporting pricing and packaging evolution. He advises early-stage and growth-stage SaaS companies to focus on architectural best practices for developing their SaaS, as well as to recognize that B2B SaaS buyers are increasingly empowered. They demand transparent pricing & packaging, the ability to buy how, when & what they want, to pay for the value they receive, and to be billed for what they use.

Keywords

SaaS, software development, career journey, AWS, solutions architect, SaaS Factory, costs, monetization, feature flags, entitlements, pricing, packaging, early-stage, growth-stage

Takeaways

Understanding costs and monetization strategies is crucial for SaaS companies as the industry evolves.

Feature flags play a significant role in managing and packaging features in SaaS products.

Entitlements are complex and often misunderstood, but they are essential for supporting pricing and packaging evolution.

Early-stage SaaS companies should focus on simplicity, customer understanding, and feature development.

Sound Bites

"What does it mean to actually build a feature in a SaaS product?"

"The ubiquity of Gen.AI is a given now."

"A lot of the technical and architectural challenges around supporting monetization as a business goes from single product to multi-product stem from how we manage features."

Chapters

00:00Introduction and Setting the Stage

05:02Understanding the SaaS Factory at AWS

09:30Trends and Inflections in Building Software Today

15:10The Complexity of Monetization in SaaS

29:45Key Considerations for Early-Stage SaaS Companies

37:25Where to Find Bill Tarr and Learn More about SaaS Factory

Matt Bradley, former CEO of Cloud Snap, shares insights on his career journey and the importance of pricing and packaging in B2B SaaS. He emphasizes the need for pricing to be aligned with the value customers receive and not out of sync with the company's cost structure. Matt also discusses the common misconceptions around pricing and the importance of collaboration between product, sales, and marketing teams. He highlights the significance of having a clear pricing philosophy and a well-designed pricing page. Matt shares a success story of ProsperOps, a company that has effectively aligned its pricing model with customer value.

Takeaways

Pricing should be aligned with the value customers receive and not out of sync with the company's cost structure.

Collaboration between product, sales, and marketing teams is crucial for effective pricing and packaging.

Having a clear pricing philosophy and a well-designed pricing page is essential for B2B SaaS companies.

Misconceptions around pricing include the belief that enterprises don't want to see pricing and that product owns monetization.

The most influential moment in Matt's career was becoming the CEO of Cloud Snap, which involved taking a significant risk and learning how to lead cross-functional teams.

Sound Bites

"Knowing when to say no"

"The price that you charge customers has to be aligned to the value a customer receives and also can't be out of whack with your cost structure"

"They have a pricing model that perfectly aligns to the customer"

Chapters

00:00Introduction and Career Journey

09:56Growing Cloud Snap's Business

15:28Exciting Inflections in B2B Software

25:23Common Mistakes in Pricing and Packaging

32:01Influential Moments in Matt's Career

37:54Collaboration and Organizational Challenges in Pricing

42:02Connecting with Matt Bradley

In this conversation, Justin Talerico, CMO at Automox, discusses his career journey and shares insights on building trust and alignment between go-to-market and product teams. He also discusses a major inflection in SaaS -- how empowered the B2B SaaS buyer has become and the importance of reducing friction in the customer experience. Justin highlights the tech stack needed to support a buyer-centric approach and the challenges and best practices of pricing and packaging. He emphasizes the need for companies to be able to action pricing and packaging research and the importance of understanding & removing operational and architectural constraints in product and engineering.

Takeaways

Building trust and alignment between go-to-market and product teams is crucial for success.

The SaaS buyer has become more empowered and expects a frictionless and personalized experience.

The tech stack should support a buyer-centric approach and enable meaningful interactions with potential customers.

Pricing and packaging require careful consideration and the ability to action research and test different options.

Operational and architectural constraints play a significant role in implementing pricing and packaging changes.

Sound Bites

"What's cool is to build a universe of people who are like-minded."

"Our ability to see intent signal in the dark funnel by account is critical."

"If your ducks aren't in a row on pricing and packaging and you can't action it and test it and say, is this better than what I had before, objectively, truly in the market, not just in theory, then a lot of it is wasted energy and wasted cycles."

In this episode, Fynn sits down with Bill Wilson, founder of Pace Pricing, to discuss his journey from software developer to pricing expert. Bill shares his insights into the intricacies of B2B SaaS monetization, common pricing mistakes, and how to build effective pricing strategies. Whether you're an early-stage startup or a growing SaaS company, this episode is packed with valuable advice on optimizing your pricing and packaging models.

Key Topics Covered:

Bill Wilson's Career Journey

Transition from software developer to founder to pricing coach

Founding MindSea and SalesRight

Acquisition by FastSpring and founding Pace Pricing

Trends and Inflections in Enterprise SaaS

Shift towards hybrid pricing models

Importance of net revenue retention

Focus on profitability post-pandemic

Building Pace Pricing

Target audience and services offered by Pace Pricing

Deep dive into data, market research, and customer insights

Importance of rigorous validation processes

Common Pricing Mistakes in SaaS

Early-stage mistakes: giving products away for free, overcomplicating pricing models

Growth-stage mistakes: not changing prices, avoiding seeking help

Misconceptions Around Pricing and Packaging

Often over-rotate on what the price should be, rather than how the product is packaged and purchased

Often don't take holistic approaches to monetization

Advice for Engineers and Product Leaders

Importance of subscription management platforms & entitlement services

Integrating pricing and packaging into product development

Supporting go-to-market creativity with agile pricing adjustments

Memorable Quotes:

"Profitability has become a key focus post-pandemic, and aligning pricing strategies with customer value is essential."

"Effective monetization strategies involve understanding customer value and aligning pricing models to match."

"Not changing prices over time is a major pitfall; stagnant pricing can lead to decreased value perception."

Resources Mentioned:

Pace Pricing

Bill Wilson on LinkedIn

Bill Wilson on X (@WDRWilson)

Call to Action: If you enjoyed this episode, please subscribe, rate, and review on your favorite podcast platform. For more insights on B2B SaaS pricing and monetization, follow Schematic on LinkedIn.

Host: Fynn Glover, Co-Founder of Schematic Guest: Bill Wilson, Founder of Pace Pricing

Marcos Rivera, founder and CEO of Pricing I/O, shares his career journey and myriad lessons learned about pricing, packaging, and monetization best practices in B2B SaaS. He discusses the challenges and complexities of pricing, including leaving money on the table and the fear of raising prices. He emphasizes the need for a clear strategy, understanding the target audience, and creating valuable experiences for customers. He highlights the importance of data collection and analysis in pricing decisions & provides insights on aligning pricing initiatives with the product roadmap. He emphasizes the role of confidence in pricing & discusses the combination of quantitative analysis and qualitative customer feedback in pricing strategies.

The conversation is packed with insights & concludes with exploration of how pricing & packaging will change against the backdrop of AI.

Link to episode: https://schematichq.com/podcast/price-with-confidence-lessons-on-pricing-packaging-and-monetization-with

Takeaways

- Pricing and packaging are crucial for B2B SaaS companies to monetize their products effectively.

- A clear strategy, understanding the target audience, and creating valuable experiences for customers are essential for successful pricing.Data collection and analysis are necessary for making informed pricing decisions.

- Aligning pricing initiatives with the product roadmap helps drive growth and customer value.

- Confidence plays a significant role in pricing, and mitigating risks can help build confidence.

- Integrating quantitative analysis and qualitative customer feedback is key to developing effective pricing strategies. Pricing is an art informed by science, with judgment playing a crucial role in understanding customer psychology and determining value perception.

- The package establishes value, while the price serves as the exchange rate for that value. Changing one without the other can lead to friction and dissatisfaction.

- Companies often face challenges in pricing and packaging due to limited visibility into customer behavior, the complexity of data and systems, and the trade-offs between development resources and tracking capabilities.

- The future of AI in B2B SaaS presents opportunities for boosting core value, creating new use cases, and driving innovation in pricing and packaging.

- Result-driven software pricing, based on tangible outcomes and value delivered, may become more prevalent as AI enables better tracking and measurement.

Sound Bites

"Pricing on purpose starts with a clear strategy."

"CEO support is crucial for successful pricing initiatives."

"Good pricing requires discipline in data collection and a structured approach."

"Pricing is more of an art informed by science."

"Price is what they pay, and the package is what they get."

"AI may drive companies to start innovating more entry points into their product."

Chapters

00:00 Introduction and Setting the Stage

03:01 Founding Pricing.io and Helping B2B SaaS Companies

06:12 Common Pricing Challenges Faced by Companies

08:10 The State of Pricing and Packaging in B2B SaaS

11:09 Pricing on Purpose: Building a Clear Strategy

13:08 The Relationship Between Monetization Initiatives and the Product Roadmap

17:25 Creating a Pricing Committee and Driving Monetization Initiatives1

9:46 Pairing Quantitative Analysis and Qualitative Feedback in Pricing

22:48 Surprises and Lessons Learned in Building Pricing I/O

24:46 Building Confidence in Pricing and Mitigating Risks

28:35 Understanding Customer Psychology and Value Perception

36:23 The Relationship Between Pricing and Packaging42:34

Challenges in Pricing and Packaging for B2B SaaS Companies

46:26 The Future of AI in Pricing and Packaging51:18Result-Driven Software Pricing: A Shift Towards Tangible Outcomes

Keywords

pricing, packaging, B2B SaaS, monetization, growth, strategy, data, customer value, confidence, pricing, packaging, B2B SaaS, customer psychology, value perception, pricing and packaging challenges, AI, result-driven software pricing

John Kotowski, founder of PricingSaaS, shares his career journey and insights on pricing and monetization in B2B SaaS. He emphasizes the importance of mindset for founders and the impact of AI on pricing strategies. John discusses the complexity of monetization in B2B companies, highlighting the lack of ownership and the need for better infrastructure and tools. He advises product and engineering leaders to align their product roadmap with pricing and packaging changes to drive growth. John also shares the influence of CEOs on his career, emphasizing the importance of conviction and grit.

Link to post: https://bit.ly/3S4SzII

Takeaways

- Mindset is crucial for founders to navigate the challenges of starting a business.

- AI has a significant impact on pricing strategies and can automate manual tasks.

- Monetization in B2B companies is complex due to the lack of ownership and the need for better infrastructure and tools.

- Aligning the product roadmap with pricing and packaging changes can drive growth.

- CEOs inspire resilience, conviction, and grit in navigating the challenges of entrepreneurship. Sound Bites

"Those skills are good and useful, but it's really about the mindset."

"The more complexity you introduce, the harder it gets on both operational and customer side."

"Monetization is converting value into dollars."

Chapters

00:00 Introduction and Career Journey

03:06 PricingSaaS and Its Mission

05:41 Lessons Learned and Benchmark Report

08:46 Changes in the B2B SaaS Market

11:38 Pricing vs. Packaging and Changes in Q1

18:43 Complexity and Challenges in Monetization

20:21 Architectural Complexity and Lack of Standards

24:54 The Role of Entitlements

26:48 Building a Standard for Monetization

29:23 Mistakes to Avoid in Scaling a Business

31:21 Formative Moments in John's Career

33:26 Closing and Contact Information

Keywords

John Kotowski, PricingSaaS, career journey, pricing, monetization, B2B SaaS, mindset, AI, complexity, ownership, infrastructure, tools, product roadmap, growth, CEOs, conviction, grit