🎧$4.4B Founder: “AI Credits Won’t Save Your SaaS”

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.

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🗒 What we covered:

[13:00] – How the tech recession forced Outreach to reinvent itself

[18:30] – Why seat-based pricing is dead and what replaces it

[34:00] – Why the Agent Economy is impossible without a new metering layer

[45:30] – Why generalist agents lose to specific domain experts

🧠 Big Ideas

#1 Tech Is a Great Starting Market, But a Terrible Place to Stay

Outreach grew by selling seat-based SaaS to tech companies. But when the market crashed and those companies cut staff, Outreach’s revenue stalled overnight. He realized tech gives you PMF, not durability. Founders must ask: Is my business built on early adopters, or on industries that survive downturns? If you want a long-term company, your revenue has to cross the chasm long before you think you need to.

#2 The Question from DocuSign’s CEO That Proved Seat-Based SaaS Is Dead

DocuSign CEO told Manny: “If your agents work, why would I hire more people next year?” That single sentence exposed the flaw behind the entire SaaS model. If headcount shrinks, seats shrink. If seats based pricing shrink, SaaS dies. Founders building AI products must stop pricing like old software. The future is not per-seat, it’s per outcome.

#3 The 10× Opportunity: Ultra-Vertical Agents That Replace Salaries, Not Seats

Manny argues that the real AI opportunity isn’t general-purpose agents, it’s vertical agents that perform specific workflows so well they replace human headcount. And when an agent replaces five SDRs or automates a mortgage workflow, it isn’t a $49/mo seat, it’s a slice of payroll. That shift from IT budgets to labor budgets is what makes the agent economy a 10× larger market than SaaS.

😲 My Favorite Quote:

“At Outreach I was paying fortunes to Zuora, Salesforce, and Netsuite, yet it felt like those systems were working against me. The status quo wasn’t neutral; it was my enemy. It was in my face, laughing, taking money out of my pocket, and reminding me I couldn’t do anything about it.

And when you get that kind of punch in the mouth, something changes. That taste of blood wakes you up. You stop thinking in terms of market opportunities and start thinking in terms of refusing to feel powerless again. You promise yourself you won’t get hit like that anymore, and you begin fixing what those systems will never let you solve.”