Jack & Jill raises $40M Series A for AI agents on both sides of hiring

Jack & Jill, a London-based startup building AI agents for job seekers and employers, said it raised a US$40 million Series A led by Air Street Capital, with participation from Creandum and Madrona. The product pairs Jack — an AI career agent for candidates — with Jill — an AI hiring agent for companies; when both sides agree there is a match, the agents introduce them directly instead of routing through a classic job application.

Same-day primary capital is going into AI that sits on both sides of hiring — candidates and employers — instead of another résumé filter or chatbot apply button. That is a concrete labor-market story, with a named lead investor and an on-record company announce.

Jack & Jill, a London-based startup building AI agents for job seekers and employers, published “$40M Series A to make warm introductions at the scale of the internet” on its company blog on 15 Sep 2026. The company said it raised a US$40 million Series A led by Air Street Capital, with participation from Creandum and Madrona. Series A is early growth funding after seed money — not a first check, and not a later growth round. That company blog, dated 15 September 2026 and signed Matthew Wilson, is the filing event. These are company claims.

Valuation and a full cap table were not disclosed on the company page.

What the product is, as the company describes it: Jack is an AI agent for a candidate’s career. Jill is an AI agent for hiring. An agent here means software that acts for a person or a company — not a human recruiter sitting in the middle. When both agents agree there is a match, they introduce the candidate and the company directly, “skipping the application altogether.” A warm introduction, as the company uses the phrase, means connecting two sides only when both look like a fit.

Traction claims, still the company’s — do not independently verify: about 380,000 people in San Francisco, New York, and London are talking to Jack, described as a voice agent; more than 5,000 companies are hiring with Jill, including Corgi, Ramp, Multiverse, Maze, and Attio. File 380,000, more-than-5,000, the three cities, and those company names as Jack & Jill’s.

Named voices on the company blog: Saaras Mehan, co-founder and chief technology officer; and Nathan Benaich, general partner at Air Street Capital. Their quotes are color only and stay in Sources. Axios Pro’s exclusive, linked from the same company page, names Matt Wilson as CEO. Matthew Wilson signed the company blog. This is not investment advice.

Prior-raise context, secondary and attributed: the company page links a TechCrunch piece on an earlier about-$20 million raise. The company PRIMARY page does not print a lifetime total.

Geography and hiring, still the company’s: it is hiring across San Francisco, New York, and London, and points open roles at jackandjill.ai/about-us.