The First Senior Hire

A dinner about hiring your first senior leader—when to do it, how it goes wrong, and what it changes. Hiring your first 'real' senior leader—a product manager, a head of sales, someone with more experience than you—is a milestone that changes your startup forever. Some founders wait too long. Others hire too fast. Many quietly question whether they've made a terrible mistake… but few talk about it out loud. At this Ascend Dinner, we'll gather a small group of founders who are navigating (or have recently navigated) this exact moment. We'll share the decisions, doubts, and discoveries that don’t make it into investor updates—like how to hand over control without losing your identity, how to spot signs of misalignment early, and what it really means to 'let go.' This isn’t a panel. There are no slides. Just one table, one conversation, and the kind of honesty that only happens when the pressure’s off and the food’s hot.

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Ascend Dinners

Connecting founders through curated dinners