When AI Knows Too Much: Personalisation That Builds Trust Vs Breaks It

Sam has spent years working with researchers to measure and improve trust across Expedia’s vacation rentals, Stitch Fix’s personalised shopping and now PayPal. In this debate, he tests his trust-first approach against a growth-focused counterpart who believes AI, targeting and ad networks are simply the price of modern digital experiences. Together they explore where personalisation genuinely helps people and where it quietly becomes manipulation, especially when money and financial identity are involved.

Outcomes:

• Design trust metrics that sit alongside conversion so you can see trust erosion before it hits revenue.
• Decide where to place hard guardrails on AI, recommendations and offers in high-trust products.
• Explain data use and personalisation in human terms so mainstream users feel safe, not exploited.
• Align product, growth, legal and research on a common definition of “too far” when using user data.