Guest: Manny Medina, CEO of Outreach

In 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:

#151 CEO Outreach, Manny Medina: 10M or Die

Grit