Former Outreach CEO Manny Medina discusses his new company Paid, which provides billing, pricing and margin management tools for AI companies. He explains why traditional SaaS pricing models don’t work for AI businesses, and breaks down emerging approaches like outcome-based and agent-based pricing. Manny shares why he believes focused AI applications targeting specific workflows will win over broad platforms, while emphasizing that AI companies need better tools to understand their unit economics and capture more value.

Hosted by Pat Grady and Lauren Reeder, Sequoia Capital

Mentioned in this episode:

CPQ: Configure, Price, Quote

Invent and Wander: Book by Jeff Bezos and Walter Isaacson

Foundations of Statistical Natural Language Processing: 1999 book by Chris Manning and Hinrich Schütze that Manny cites as a piece of AI content every AI founder should read. (still in print, companion site here)

The fox and the hedgehog: 

Quandri 

XBOW

HappyRobot 

Owl

Crosby