Jack & Jill raises $40M Series A led by Air Street for AI career matching
nathanbenaich · x · 2026-09-15
Air Street Capital founder Nathan Benaich announced he led a $40M Series A for Jack & Jill, an AI career-matching startup, with Madrona Ventures and Creandum participating.
- Earlier this year a founder in Air Street's portfolio tried the product and urged him to invest, calling it a "top tier AI product"
- CEO Matt Jon Wilson frames the problem: most people leave one of life's biggest decisions—how they spend their work time—almost entirely to chance
- Each search digs into what motivates someone, what they excel at, and what they'd love to do next to match talent with opportunities
Related event: Air Street leads $40M Series A in AI career-matching startup Jack & Jill(5 posts)→
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