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 Monetization should be treated as a first-class citizen from the beginning of a company's journey. A clear pricing and packaging strategy is crucial for success.

Legacy pricing models need to be maintained while introducing new products and features. Building and maintaining monetization infrastructure requires collaboration between product, engineering, and business teams. Monetization infrastructure should be agile and adaptable, with a central point of truth for entitlements and feature flags.

Extracting services for entitlements and other monetization needs can enhance agility and experimentation. A well-designed product catalog can serve as a unified policy file and source of truth for products and entitlements.

B2B software should prioritize flexibility and transparency to meet the expectations of empowered customers. Embracing uncertainty and prioritizing personal work-life balance are crucial for career growth and success.

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