Jack & Jill Raises $40M for AI Job Matchmaking

Jack & Jill, operated by Tinker Tailor Talent Ltd., has raised $40 million in a Series A round led by Air Street Capital, bringing its total funding to $60 million. The platform uses two AI agents to eliminate traditional job applications, with Madrona, Creandum, and Entrepreneurs First also participating. The platform pairs Jack, a voice-based AI career coach for job seekers, with Jill, an AI that learns employer hiring needs. Together, the agents have arranged over 25,000 interviews across 5,000 companies, handling 5,000 new matches monthly without resumes or manual screening.