Sales Tech Showdown with Alastair Woolcook - The Transaction - Ep # 14

In this episode of The Transaction, Matt Amundsen and Craig Rosenberg are joined by Alistair Wolcock, a renowned expert in sales tech and AI. Together, they explore the current trends and future disruptions in sales technology, the importance of user experience, and the concept of signal-based selling. Alistair shares his insights on how enterprise buyers are adapting to new technologies and the vital role of data in driving sales and marketing strategies. Tune in for a deep dive into the future of sales tech and actionable advice on staying ahead in the competitive business world.

 • Sales tech vendors often overwhelm enterprise buyers with advanced features, neglecting the basic functionalities buyers need.
 • Microsoft’s Copilot and similar AI solutions are set to disrupt high-cost vendors by integrating essential features into everyday applications.
 • Achieving desired outcomes within six clicks is crucial for user adoption and success.
 • The difference between fast innovation (incremental improvements) and disruptive innovation (game-changing advancements) is vital for understanding market dynamics.
 • CIOs are increasingly repatriating data to on-premises to maintain control and leverage AI internally.
 • Warehouse-native applications will be essential as customers demand direct access to their data.
 • Signal-based selling focuses on actionable insights rather than just data analytics, driving more effective sales processes.
 • Consolidation of marketing and sales operations into pod structures can significantly improve efficiency and results.


 • 02:00 Icebreaker and Spirit Animals Discussion
 • 05:00 Welcoming Alistair Wolcock
 • 07:00 Enterprise Buyers vs. Sales Tech Vendors
 • 12:30 Impact of AI and Generative AI in Sales Tech
 • 17:00 Importance of User Experience in Sales Tech
 • 20:00 Fast Innovation vs. Disruptive Innovation
 • 25:00 Data Ownership and Repatriation Trends
 • 30:00 Warehouse Native Applications and Data Access
 • 35:00 Signal-Based Selling Explained
 • 40:00 Consolidation and Operational Integration
 • 45:00 Lessons from B2C E-commerce for B2B Companies
 • 55:00 Outro and Final Thoughts

Quote of the Show:
“Signals to me are about the action, not about the insight.” - Alistair Wolcock

Connect with Alistair Wolcock:
 • LinkedIn: Alistair Wolcock

 • Brent Adamson: For insights on pod structures.
 • Dave Gerhart: For the book “Founder Brand.”
 • Lars Van Dam: For research on user experience and market performance.

Ringmaster Conversational Marketing - The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through branded podcasts. Learn more at

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Creators and Guests

Craig Rosenberg
Craig Rosenberg
I help b2b companies grow revenue by enabling GTM excellence. Chief Platform Officer at Scale Venture Partners
Matt Amundson
Matt Amundson
CMO, Advisor, Data-Driven Revenue Leader. Chief Marketing Officer of Census
Sales Tech Showdown with Alastair Woolcook - The Transaction - Ep # 14
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