Outreach to Paid: Manny Medina on GTM debt, pipeline, hiring, & AI agents

In this SaaStock Europe keynote, Manny Medina, Co-founder and CEO of Paid (and former CEO at Outreach) talks through the real operational patterns behind taking a SaaS company from zero to $200M+ ARR, and how those patterns are shifting in an era of AI agents. Drawing on his experience building Outreach to hundreds of millions in ARR and now starting again from scratch, Manny covers: - How GTM and process debt quietly build up from $0–$1M, $1–$5M, $5–$25M and $25–$50M+. - Why most teams misread pipeline, then over-hire or hire in the wrong order. - The maths and behaviour changes needed to build reliable, repeatable pipeline. - How culture, onboarding and poor process design make every new hire slower, not faster. - Why the next wave of SaaS will be driven by AI agents, not just human seats. - What changes when you move from per-seat pricing to agent-based monetisation. - Why your current back-office stack and metrics aren’t built for an agent-first world. 🔔 Subscribe for the latest content from SaaStock conferences and weekly episodes of The SaaS Revolution Show. 00:00 - Introduction - The Outreach journey 04:50 - The cost of hiring beyond headcount 07:26 - How to build efficient sales processes from day one 10:26 - Engineering truths: Building fast vs building right 12:00 - Building process discipline and avoiding debt creep 13:45 - Building a culture of customer obsession 15:00 - Paid and growing in the AI agent economy 16:29 - Why AI agents need new economics 18:35 - Archetypes for successful AI monetisation 21:27 - How to show the value of AI agents and drive higher ACV deals 23:30 - Why better AI means compressed margins 24:15 - The Paid journey and tracking ACV #saas #saastockeurope #scaleup #founders #agenticai #aimonetization #saasgrowth #founderlessons