Air Street leads $40M Series A for AI job-market startup Jack & Jill

nathanbenaich · x · 2026-09-15

Air Street Capital has led a $40M Series A in Jack & Jill, an AI talent marketplace that puts agents on both sides of hiring — representing candidates beyond their resumes and matching them with employers. Madrona joined the round, with existing investors Creandum and Entrepreneurs First participating, less than a year after the company's $20M seed. Investor Nathan Benaich says the deal was triggered by a portfolio founder who called it a "top tier AI product" after trying it. The post also outlines Air Street's approach to sourcing deals through its founder and expert network.

Related event: Air Street Leads $40M Series A in AI Career Matching Startup Jack & Jill(5 posts)→

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