Timing, Market Education and AI Risks

Timestamps:

16:11 - The Role of AI in Expense Management

22:20 - Fundraising and Partnering with Sequoia

39:09 - Maintaining Urgency in Growth

51:02 - The Decision to Sell: Timing and Strategy

Episode description:

Philippe Sahli is the Co-Founder and former CEO of Yokoy, the Swiss-built platform that automated spend management for mid-to-large enterprises using AI (acquired by Perk). In this episode, he shares how his path through corporate life and as CFO at Beekeeper shaped his founder instincts, his Switzerland-first network advantage, and the ambition to build “expenses on autopilot” into a global category leader.

Philippe shares how Yokoy found early product pull (customers referring customers) and what real product-market-fit signals looked like before scaling, raising an $80M Series B led by Sequoia, and navigating the “go big or go home” reality that comes with hypergrowth.

Philippe also opens up about the role of naivety as a superpower in entrepreneurship, the culture risk of losing sense of urgency and stop pushing after big funding, and what it feels like to shift from being CEO to becoming Chief Spend Officer inside a much larger organization.

The cover portrait was edited by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.smartportrait.io⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

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