Evolution of Pricing Strategies in Business with Gary Bailey

30/10/2025 44 min
Evolution of Pricing Strategies in Business with Gary Bailey

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Episode Synopsis

I am thrilled to have Gary Bailey, founder of Strategim, a monetisation & pricing expert with a deep background in financial services, accounting, pricing, and AI. In this conversation, Gary Bailey, a monetisation and pricing expert, shares his journey from accounting to product management and pricing. He discusses the importance of pricing as a core discipline in business education, the evolving role of finance in pricing strategies, and the impact of AI on SaaS pricing models. Gary emphasizes the need for training the next generation in pricing and the role of a monetization architect in modern businesses. He also highlights common pricing mistakes, the importance of starting the monetisation journey with a feature list, and the need to redesign business education to adapt to the changing landscape. Timestamps 06:00 The Importance of Pricing in Business Education 09:17 Balancing Certainty and Uncertainty in Pricing 13:17 The Evolution of SaaS Pricing with AI 16:50 Training the Next Generation of Pricing Professionals 20:35 The Role of a Monetization Architect 22:26 The Architecture of Pricing Strategies 23:37 Evolving Pricing Models in SaaS 25:58 The Impact of AI on Job Markets 29:19 Preparing for an AI-Driven Future 32:17 Learning from Pricing Mistakes 33:48 Rebundling Features for Better Monetization 36:12 Rethinking Business Education in the AI Era Gary's Links  LDN/ X – https://www.linkedin.com/in/gary-bailey-monetization-cfo/ Website – My Links  Podcast: https://lifeselfmastery.com/itunes Newsletter: https://partner-grow.beehiiv.com/subscribe YouTube:  youtube.com/lifeselfmastery Twitter: https://twitter.com/rohitmal LinkedIn: https://www.linkedin.com/in/rohit857/

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