From Pivot to Powerhouse: How Manny Medina Built Outreach to $4B

How did Outreach, born out of a pivot, go from a nearly empty bank account to a $4B valuation? We chat with Manny Medina, co-founder of Outreach and now of Paid.ai, to hear his thoughts on customer obsession, pivots, and the future of AI agents. Listen on Spotify: https://open.spotify.com/episode/2mAH4hgIfJha2UrzCAW4gL?si=Lb1kQfl5TuiBe9MqeFBobQ Learn more: https://www.enterpret.com Timestamps: 00:15 – Intro to Manny Medina, co-founder of Outreach and Paid.ai 00:36 – Outreach’s origin and near-failure pivot 01:30 – Customer obsession born from survival 02:22 – The call that proved product-market fit 03:15 – Lessons from scaling Outreach to enterprise 03:44 – Selling door-to-door and learning from users 04:34 – Handling customer tickets personally 04:59 – Rethinking the roadmap and building flexibility 05:51 – Building for customers, not the roadmap 06:16 – Why “code is cheap, customers are not” matters 06:37 – Paid.ai and the new agent economy