Pod: Previous Retailer and Demandware/Salesforce Commerce Agency SVP Starts Agentic Startup: Kyle Montgomery
On this week’s episode of the Retailgenic podcast , we learn how having 20 nieces and nephews inspired him to take the entrepreneurial plunge...
This week I sit down with Kyle Montgomery, Founder and CEO of Generous, an AI-powered gifting assistant designed to take the mental load off remembering birthdays, picking the perfect present, and even executing the purchase.
Kyle is a first-time founder with over 15 years of e-commerce experience, most recently serving as SVP of Commerce at Astound Digital. His career has spanned development, architecture, and go-to-market leadership roles for platforms like Salesforce Commerce Cloud, Shopify, and Adobe Commerce.
Listen/Watch Our Interview:
In this episode, Kyle and I go deep into the world of AI gifting. Tune in to hear about:
Kyle’s path from agency executive to startup founder
The very personal pain point (20 nieces and nephews!) that inspired Generous
Why gifting is the ideal vertical for AI shopping agents
How Generous combines contact syncing, contextual recommendations, and event-based planning with a touch of wishlists.
The power of human-in-the-loop design in Agentic commerce
A future where gifting is easier (and more thoughtful) thanks to your personal AI assistant
3 Highlights You Shouldn’t Miss:
Gifting Is the #1 Use Case for AI in Shopping – Kyle references Salesforce data and Adobe studies showing that people want help finding meaningful gifts.
No Search Bar, No Problem – Generous is launching as a fully agentic interface with no product listing pages, only conversation.
"I've Got You" Energy – The agent isn't here to replace you; it’s here to have your back when life gets busy. It's gifting help that feels human.
Join the Waitlist
Want to try it out? Sign up at meetgenerous.com to join the beta. And yes, share with friends to jump the waitlist.
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Up next…
Next week we’re sharing our demo of Perplexit’y Comet Agentic Browser (just in case you missed seeing it live).
Subscribe and Stay tuned!
Thanks very much @Scot and the Retailgentic / ReFiBuy.ai team for having me on!
It's amazing how fast agentic commerce is evolving, every week, every day, every hour. 🚀