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.com
Follow Kyle: https://www.linkedin.com/in/kyleamontgomery/

⏱️ Key Timestamps:

Timestamps:
00:00 – Hands on the wheel: what autonomy in gifting looks like
02:05 – Meet Kyle Montgomery, founder of Generous
04:00 – Kyle’s background: From Demandware to Estound Digital
06:00 – What sparked the idea for Generous? (Hint: 20 nieces + no app)
11:00 – Generous: What it is and who it's for
13:00 – Contact syncing, user onboarding, and AI-powered suggestions
18:00 – No search bar?! The power of chat-first shopping
22:00 – Agentic checkout and payment flow
27:00 – The humanity of gifting—why agents shouldn’t replace people
30:00 – 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 Commerce
41:00 – Where to sign up + what’s next for Generous

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