CX is reaching a tipping point - Interview with Jonathan Rosenberg of Five9

CX is reaching a tipping point - Interview with Jonathan Rosenberg of Five9

Author: Adrian Swinscoe | Customer Experience Strategy Expert November 13, 2025 Duration: 41:01

Today’s episode of the Punk CX podcast features a discussion I recently had with Jonathan Rosenberg, who is the Chief Technology Officer and head of AI at Five9. Jonathan and I talk about why he believes CX is reaching a tipping point and what’s driving that, how things are likely to change for customers, agents, and businesses, what he’s seeing companies do well/right, as well as what to avoid in order to better harness the obvious potential of AI.

This interview follows on from my recent interview – How Vodafone, Rabobank and others are driving meaningful results with AI – Interview with Matt Healy of Pega – and is number 562 in the series of interviews with authors and business leaders who are doing great things, providing valuable insights, helping businesses innovate and delivering great service and experience to both their customers and their employees.


There’s a lot of noise around customer experience, but Punk CX: Customer Experience Insights with Adrian Swinscoe cuts through it with conversations that feel more like a strategic workshop than a standard interview. Host Adrian Swinscoe, a customer experience strategy expert, brings a distinctively pragmatic and often contrarian perspective to each discussion. He sits down with a wide range of industry leaders, from entrepreneurs to seasoned executives, to unpack what it really takes to build an organization that people genuinely want to engage with. You’ll hear them delve into the interconnected mechanics of customer service, customer engagement, and the often-overlooked driver of it all: employee experience and engagement. The dialogue naturally explores how technology, from AI to broader digital transformation, can be leveraged practically rather than just hyped, and what it means to build adaptable, responsive organizations with high-performing teams at their core. This podcast moves beyond theory, focusing on the actionable insights and sometimes uncomfortable truths that define modern customer and business strategy. Each episode is designed to give you a tangible takeaway, whether you’re refining your own approach or challenging the status quo within your company.
Author: Language: English Episodes: 50

Punk CX: Customer Experience Insights with Adrian Swinscoe
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