After requests for another pricing episode, CJ sits down with returning guest Jason Kap, the founder and CEO of Blue Rocket, a long-tenured Microsoft leader, and an expert in pricing and packaging. Together, they take a deep dive into the evolution of software pricing, tracing its journey from the early days of buying hardware and software together to buying software separately, and all the way through the eras to the emergence of SaaS and today’s usage-based and hybrid models. Jason provides a detailed look at the shifts in the industry, including the rise of application service providers and outsourced infrastructure. As they discuss the current landscape, they highlight the importance of transparency and value abstraction. Then they look to the future with advice on how CFOs can navigate pricing in the new era of AI. Packed with practical insights, this episode offers a comprehensive guide for anyone looking to understand the past, present, and future of software pricing and packaging.

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TIMESTAMPS:(00:00) Preview and Intro(02:26) Sponsor - Planful | Mercury(04:51) Hardware and Software Sold Together(08:11) Software Sold for Hardware(11:48) The Origins of the Enterprise Agreement(15:44) Sponsor - NetSuite | Maxio | Leapfin(18:42) Application Service Providers(23:00) The Evolution of AWS, Google, and Salesforce(27:06) Outsourced Infrastructure and SaaS(33:54) Adobe as the Prime Example of Moving to SaaS(36:32) The Financial Implications of Transitioning to SaaS(38:46) Shelfware in the Next Wave(41:01) Usage-based Pricing(44:25) The Hybrid Model(48:29) Tips for Billing and Overages(52:14) Predictions for the Next Wave: How to Price AI(54:18) Wrap

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The Evolution of Software Pricing and Packaging with Pricing Expert Jason Kap

Run the Numbers