In this episode of the Monetizing SaaS podcast, we sit down with Jake Stein, a serial founder and CEO of Common Paper. Jake shares his journey from building RJ Metrics (acquired by Magento) to Stitch (acquired by Talend), and now tackling inefficiencies in B2B contracts with Common Paper.

Here are some of the highlights:

• The Journey to Entrepreneurship: Jake's fascination with technology and business started young—from a landscaping business in high school to founding RJ Metrics after realizing he wanted to be on the "founder side" of the calls he took as a VC analyst.

• Lessons Learned from RJ Metrics: Not anticipating the impact of emerging technologies like Amazon Redshift taught him the importance of staying ahead of ecosystem changes and their downstream effects on business strategy.

• Insight Behind Common Paper: Contracts should be treated as APIs, not digital pictures of paper, to unlock interoperability and streamline processes for businesses.

Other Takeaways - Mistakes made at RJ Metrics taught valuable lessons about market evolution and technology. - Common Paper aims to revolutionize contract management in the B2B SaaS industry. - The significance of having a consistent data model across contracts for better integration. - The initial pricing model was overly complex and confusing for customers. - Switching to a simpler pricing model reduced customer inquiries significantly. - Customer feedback is crucial in shaping product and pricing strategies. - Raising prices can lead to better revenue growth despite initial customer acquisition dips. - Understanding the psychology behind pricing can enhance customer confidence. - A low price can sometimes signal a lack of value to potential customers. - Iterative changes in pricing can lead to substantial business impacts.Learning from past experiences is essential - for future decision-making.

Chapters 00:00 The Journey of a Multi-Time Founder

10:27 Lessons from RJ Metrics and Stitch

18:52 The Insight Behind Common Paper

27:00 Targeting Early Stage Startups

34:02 The Journey of Pricing and Packaging

47:01 Lessons from a Sales Call #pricingtips #saas #ycombinator