A London startup betting that hiring works better when software represents both sides has closed a €34.68M ($40M) Series A. Jack & Jill runs two agents, one for people hunting jobs and one for the companies hiring them.
Air Street Capital is the lead investor. Madrona and Antler, two funds new to the company, also took part. Ada Ventures, Creandum, Repeat.vc, Expedite Capital and Entrepreneurs First came back for another round, while Dig Ventures, Playfair, Firedrop and Episode 1 joined in as well.
Matt Wilson and Saaras Mehan started the company in March 2025. Jack is the agent that talks to candidates, in voice sessions that feel closer to coaching than a job-search chatbot. One user called Jack 144 times, and the company says users have logged 12,000 hours of conversations with him.
Jill works for employers, digging into job descriptions and company research before tapping Jack’s network for names rather than wading through open applications. Introductions happen only when both agents agree the fit is real.
Total funding reached €52.9M ($60M) with this round, after a €18.3M ($20M) seed in October 2025. The new cash mostly funds American expansion, following launches in San Francisco and New York this year.
“The next leap in hiring will not come from better searches over the same resumes,” said Air Street Capital general partner Nathan Benaich, who argues that brokered introductions, not better filters, are what the market is missing.
