I Built a $4.4B SaaS and AI Agents Destroyed It: The End "Per Seat" Pricing

My guest today is Manny Medina, the founder who defined the last decade of sales tech with Outreach and is now building Paid.ai , the infrastructure for the next decade of AI.

Manny’s path took him from a shrimp farm in Ecuador to the heights of Silicon Valley, where he built Outreach into a $4.4B SaaS. But in 2023, a conversation with the CEO of DocuSign handed Manny a "Red Pill" moment: if AI agents do the work of humans, companies will hire fewer people, and the seat-based SaaS model will collapse .

He realized the current infrastructure—giants like Salesforce, Netsuite, and Datadog—was "conspiring against him." They could track closed deals or API calls, but they couldn't distinguish between an agent's cost (tokens) and its value (reasoning) . 

Manny founded Paid to solve this: a way to interpret agent behavior so builders can stop selling cheap software and start selling valuable work. Paid has raised +$30M from investors like Sequoia, Lightspeed and EQT.

What we covered

• Why the Agent Economy is impossible without a new metering layer

• Why seat-based pricing is dead and what replaces it