Guest: Manny Medina, CEO of OutreachIn its Seattle headquarters, the sales execution platform Outreach has at least one wall covered in AI diagrams and architectural flows. CEO Manny Medina says that’s because he believes “there’s no world in which reps don’t have an assistant the way that coders do.” The AI revolution has also given Manny — who got his M.A. in computer science at Penn — a chance to be more hands-on than your average CEO of a $4 billion company. “I try not to think myself as a CEO,” he says. “I try to think myself as a team member that is doing something useful.”In this episode, Manny and Joubin discuss northern New Jersey, American opportunity, going to the future, crossing the chasm, jujitsu, Tony Robbins, winning on your own terms, shifting motivations, inspiration through transparency, Moonwalking with Einstein, Lululemon, hands-on CEOs, and “been there, done that.”In this episode, we cover:Leaving Ecuador for the US (02:21)Would Manny do it all again? (07:45)Finding product-market fit (10:09) Scaling, scarcity, and stability (14:41)AI-assisted sales reps (18:59)Winner takes most (24:20)Placing long-term bets (26:42)Imposter syndrome and chips on your shoulder (32:59)“Ten million or die” (35:15)Irrational forces (42:33)Manny’s weekly internal emails (44:17)Memorizing names and making sacrifices (48:00)Personal and professional goals (52:23)“All the other jobs were taken” (56:53)Do-overs (01:00:18)Bad and good startup advice (01:03:24)Who Outreach is hiring and what “grit” means to Manny (01:05:58)Links:Connect with MannyLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Manny Medina, CEO and Co-founder of Outreach, discusses the revolutionary role of AI in sales, emphasizing how it enhances personalized communication while retaining human connections. He explores the shift from spammy outreach to meaningful engagement, asserting that AI empowers sales reps rather than replaces them. Manny delves into the necessity of unlearning traditional habits to fully harness AI's potential and improve productivity, highlighting the need for empathetic communication in sales strategies for future success.

Manny Medina, the visionary founder and former CEO of Outreach, dives into his latest venture, Paid, which aims to revolutionize how AI agents earn their keep. He discusses innovative billing strategies tailored for the unique challenges of pricing in the AI landscape. With insights into enhancing profitability for businesses leveraging AI, Medina sheds light on the future of agentic startups. This engaging conversation showcases how technology is evolving to support the financial needs of intelligent bots.