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.

Here are the highlights of my chat with Jonathan:

• The Rise of the Agentic CX Era: Driven by consumers using AI in their personal lives, expectations are soaring for a new “agentic CX era” where customers anticipate highly personalized, conversational, and flexible “super-agent” experiences that outperform human speed and capability.
• Enterprise ROI is Dual-Focused: For businesses, the adoption of AI agents is driven by the consistent goals of achieving reduced operating costs and increasing customer satisfaction, with reduced need for human agents on routine tasks being a key lever.
• The Pinnacle of Experience is a Blend: The best-of-breed companies will achieve success by perfectly blending human and AI agent experiences, ensuring that humans handle higher-value, more emotional, and empathetic engagements.
• Multimodal is the Future Interface: Future interfaces will be multimodal, allowing customers to fluidly speak, type, or interact with visual elements (like a flight seat-picker widget) on a turn-by-turn basis, using the best modality for the specific information exchange.
• Data Quality Drives AI Performance: The success of AI systems is contingent on data quality. Leveraging generative AI for deep personalization requires providing it with rich context about the user, company, and real-time situations to ensure accurate and relevant responses.
• A Rigorous Process is Non-Negotiable: Despite the excitement, AI still has accuracy and “hallucination” problems. Success requires a rigorous, systematic process—often called an ‘AI Blueprint’—that focuses on identifying clear use cases, securing working data sources/APIs, and defining measurable success.
• Adopt the Tortoise Mentality: Senior executives should avoid the “Hare” approach—rushing to adopt the latest startup-built AI for a quick demo. Instead, follow the “Tortoise” approach: be deliberate, methodical, and focus on the continuous loop of ‘monitor, improve, deploy’ for long-term, scalable ROI.
• Prioritize Low-Complexity, High-ROI: Initial AI efforts should focus on low-complexity, high-return-on-investment cases—not “science-fiction amazing stuff.” Automating common, repetitive tasks like password resets provides immediate, quantifiable success.
• Human Agents are Essential for Knowledge Curation: Enterprises cannot eliminate human agents because they are critical for overseeing, monitoring, and continuously curating the knowledge used to train the AI. A continuous, human-driven feedback loop is necessary to maintain accuracy and adapt to new products and services.
• The Next Wave is Concierge AI: Look ahead to ‘background agents’ or ‘research agents’ that work on a customer’s behalf even when not actively conversing, transforming CX from reactive support to a proactive, personalized concierge service that was once only affordable to the wealthy.
• Jonathan’s best advice: Automate the routine and humanize the complex. AND Make your data work harder.
• Jonathan’s Punk CX brand: Puma.

About Jonathan

Jonathan Rosenberg is the Chief Technology Officer and head of AI at Five9. Jonathan has dedicated his career to transforming the telecommunications industry and joins Five9 from Cisco where he was CTO for the Collaboration Technology Group (CTG). Jonathan is also well known for his authorship of the SIP protocol, which is the foundation for modern IP-based telecommunications. Prior to Cisco, Rosenberg was the Chief Technology Strategist at Skype, where he guided the company’s technology strategy. He received his bachelor’s and master’s degrees from MIT and holds a PhD in electrical engineering from Columbia University.

In 2002 he was named one of the most innovative young technologists in the world by Technology Review magazine. He also was named a “Top Supergeek” by CRN and won a Pulver Von Pioneer award for contributions to the VoIP industry. In 2015 he was presented with the Ohio University Strowger Award for transformational innovation in the Telecommunications industry.

Find out more about Five9, say Hi to them on X (Twitter) and Instagram @Five9 and @five9_inc respectively and feel free to connect with Jonathan on LinkedIn here.

Credit: Photo by Tim Marshall on Unsplash