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Evolution of Pricing Strategies in Business with Gary Bailey

Evolution of Pricing Strategies in Business with Gary Bailey

Update: 2025-10-30
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Description

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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Evolution of Pricing Strategies in Business with Gary Bailey

Evolution of Pricing Strategies in Business with Gary Bailey