Building Software and Navigating Chaos; Lessons from Larry Wolff

Software Meets Business

In this episode of Software Meets Business, Rich sits down with Larry Wolf, founder and CEO of Wolf Strategy Partners, to explore the critical intersection of strategy, operations, and technology. Larry shares a fascinating journey from shaping Expedia with Microsoft in the early days of the internet, to leading transformational initiatives across healthcare, publishing, and education sectors.
We unpack why digital transformation is not just about technology, but about creating clear business value, aligning with enterprise strategy, and deeply understanding your data’s potential. From startup advice on market validation to enterprise insights on change management, this episode is packed with actionable wisdom.
Whether you’re building a startup, scaling a product, or navigating AI’s role in transformation, this conversation is a must-listen for forward-thinking leaders.
Topics covered:
•The story behind the creation of Expedia
•Aligning software with business needs
•Why most digital transformations fail
•The critical role of market research and differentiation
•AI’s real-world applications in healthcare and beyond
Tune in and discover how strategy-led innovation drives real success in the digital age.

Host; https://www.linkedin.com/in/rbundock/
Sponsor; https://headchannel.co.uk/