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. This desk did not see the term sheet.

Valuation and a full cap table were not disclosed on the company page. File the US$40 million figure, the Air Street lead, and Creandum and Madrona as participants as Jack & Jill’s. This desk is not inventing a valuation, an ownership percentage, or a check size.

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. File that picture as Jack & Jill’s. This desk did not run the product.

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. This desk did not count the people or the employers.

Named voices on the company blog: Saaras Mehan, co-founder and chief technology officer; and Nathan Benaich, general partner at Air Street Capital. File those names and titles as the company’s. Their quotes are color only and stay in Sources. Axios Pro’s exclusive, linked from the same company page, names Matt Wilson as CEO. File that CEO title as Axios / the company link — not a second title invented here. 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. File that earlier figure as TechCrunch’s, via the company link. The company PRIMARY page does not print a lifetime total. This desk is not adding the two rounds into a “total funding” number the company did not state.

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. File those cities and the careers URL as Jack & Jill’s. This desk did not count headcount.

PRIMARY here: Jack & Jill’s 15 Sep 2026 company blog — Tier A company source, the original record. Discovery / corroboration: Axios Pro’s exclusive, linked from that page, and TNW’s 15 Sep 2026 write-up — not sole sources and not a second originating company text. The US$40 million Series A, the Air Street lead, Creandum and Madrona, the Jack / Jill pairing, the skip-the-application pitch, the 380,000 / 5,000-plus traction claims, the named customer logos, the Mehan and Benaich titles, and the San Francisco / New York / London hiring line are company-attributed. The CEO title for Matt Wilson is Axios / company-link attributed. The earlier about-$20 million raise is TechCrunch-attributed via the company link. NOT claimed: a valuation, a full cap table, a lifetime “total funding” sum, revenue, independently verified user or company counts, interview or hire counts from secondary write-ups, that this desk tested Jack or Jill, a stock tip, or investment advice. Distinct from the already-filed flam-40m-series-b, alphapai-50m-series-b, synapse-analytics-13m-series-a, and nuance-labs-50m.