10. Why Most AI Customer Experiences Fall Flat [Rikki Singh, Twilio]

Most enterprise AI investments in customer experience are stuck somewhere between a demo and a disappointment. The Qualtrics 2026 Customer Experience Trends Report found that nearly one in five consumers who used AI customer service saw zero benefit from the interaction. The bar for what enterprises are calling AI innovation is shockingly low, and customers feel it every time they're routed to a bot that reads from an FAQ.

Rikki Singh leads product innovation at Twilio. Before Twilio she was at McKinsey, where she co-authored the definitive research on what makes a great PM. Before that she was a PM at Microsoft. She's now running the team behind what Twilio is calling its biggest launch in 17 years — an agent-native channel with conversation memory across voice, text, and email.

In this episode we cover:

➜ Why most AI customer experiences are still just RPA with better packaging — and the right metric to anchor on instead

➜ Why token consumption made AI spend as unpredictable as AI ROI, leaving enterprise decisions with uncertainty on both sides

➜ Why the LLM wrapper creates false confidence — the model is not thinking, it's generating strings non-deterministically

➜ Vitamins vs painkillers: how to parse the signals customers don't say out loud from the ones that don't actually matter

➜ How to protect long-horizon bets inside a public company: separate PMs by horizon and celebrate what you disprove

➜ Why the brand owns the accountability when AI gets a high-stakes interaction wrong, regardless of which vendor caused it

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