Jack & Jill

AI Recruiting · HR Tech · AI Agents

Funding

Jack & Jill raises $40M Series A for dual AI hiring agents

The startup won't disclose how many of its 25,000 arranged interviews actually turned into hires.

• London-based Jack & Jill raised a $40 million Series A led by Air Street Capital, bringing total funding to $60 million less than a year after its $20 million seed.
• Jack & Jill runs two AI agents: Jack holds voice conversations with job seekers about what they want, while Jill interrogates employers about what a role actually requires, and the two introduce a match directly, no application required.
• Madrona and Antler joined as new investors, while Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc returned from the seed; the company did not disclose a valuation.
• Jack's candidate network has grown tenfold since the seed to 350,000 people, and 5,000 companies including Ramp, Attio and Multiverse have used Jill, together arranging 25,000 interviews, now running at 5,000 a month.
• CEO Matt Wilson previously co-founded Omnipresent, an employer-of-record startup he built to a $600 million valuation before its 2025 sale to Deel.
• Air Street general partner Nathan Benaich, who led the round, said the next leap in hiring will come from putting an agent on both sides of the table rather than better resume searches or more automated outreach.
• Jack & Jill is betting that agent-to-agent matching can replace the resume-and-application funnel entirely, but investors are funding the introduction mechanism before seeing proof it reliably converts to hires.