In this conversation, Fynn 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 within 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