Generous: The AI Gifting Assistant Changing How We Shop | Kyle Montgomery, CEO @ Generous

Kyle Montgomery, founder of Generous, joins Retailgenic to talk about building an AI-powered gifting agent that actually feels human. From his background in e-commerce to the "20 nieces and nephews" moment that sparked his startup journey, Kyle unpacks what it takes to build an agentic marketplace and why gifting is the perfect place to start.Sign up for the waitlist: https://meetgenerous.comFollow Kyle: https://www.linkedin.com/in/kyleamontgomery/⏱️ Key Timestamps:Timestamps:00:00 – Hands on the wheel: what autonomy in gifting looks like02:05 – Meet Kyle Montgomery, founder of Generous04:00 – Kyle’s background: From Demandware to Estound Digital06:00 – What sparked the idea for Generous? (Hint: 20 nieces + no app)11:00 – Generous: What it is and who it's for13:00 – Contact syncing, user onboarding, and AI-powered suggestions18:00 – No search bar?! The power of chat-first shopping22:00 – Agentic checkout and payment flow27:00 – The humanity of gifting—why agents shouldn’t replace people30:00 – What happens when brands no longer need websites?34:00 – Are agencies ready for the agentic future?38:00 – Kyle’s thoughts on Scott’s 5 Levels of Agentic Commerce41:00 – Where to sign up + what’s next for Generous📰 Subscribe to the free Substack: retailgentic.ai📺 Watch episodes on YouTube: youtube.com/@retailgentic🎧 Listen wherever you get your podcasts: Spotify, Apple, etc.