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

• Culture and trust are crucial in scaling a company, and they can be intentionally built through vulnerability and shared experiences.

• Pricing and packaging in B2B SaaS can be complex and require careful consideration of the customer funnel, from purchase to feature consumption.

• Architectural components of monetization include Salesforce CPQ, billing systems, and provisioning.

• A strong foundation of core values provides a lens to ensure that culture evolves in the desired direction.

• Building a provisioning system is necessary to adapt to changing pricing and packaging models.

• Turning pricing changes into a metadata exercise can streamline the process and reduce the need for extensive engineering projects.

• Aligning the product roadmap with the monetization roadmap is crucial for capturing the value of new features and capabilities.

• Decoupling pricing and packaging from application code can improve application design and flexibility.

Sound Bites

• "All of this comes down to trust."

• "Culture kills strategy."

• "Poorly managed pricing and packaging can be a very significant, a very expensive challenge for companies."

• "That event was like a major rework to pricing and packaging. The goal was to turn pricing changes into a metadata exercise."

Chapters

00:00Introduction 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