Rewriting Corporate Culture: How Chili Piper Scales with Humans, AI Agents, and Radical Decision-Making w/ Alina Vandenberghe, Co-Founder at Chili Piper

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What happens when an engineer-turned-entrepreneur brings B2C energy to B2B enterprise software and a borderline obsession with fixing broken meetings? You get Alina Vandenberghe—co-founder and Co-CEO of Chili Piper, the woman who turned scheduling software into a billion-dollar empire while managing teams across 38 countries (and somehow still finds time to make her employees build AI agents).

From starting work at 8 years old to building stealth iPad apps that caught Steve Jobs' attention, Alina's journey is equal parts inspiring and remarkable. In this episode, Becca sits down solo with one of enterprise software's most magnetic leaders to discuss how she turned corporate culture on its head.

You'll discover:
— Her early career wins (including a New York Times interview before she could barely speak English)
— Chili Piper's radical approach to decision-making and culture design
— Why every employee is required to build AI agents
— How LinkedIn became her unexpected writing school
— Why parenting, product-building, and personal growth are all connected by the same thread: curiosity

This episode is packed with tactical ideas and vulnerable reflections—from the power of documentation to the messiness of leadership to what it means to find joy while you're building something hard. Stick around for walkout songs, emoji debates, and a rapid-fire round featuring your favorite unhinged “hiccups or pinkies” question.