Jack & Jill, the London startup that puts an AI agent on each side of the job market, has raised £30M in a Series A led by Air Street Capital.
Hiring has turned into a volume game that neither side is winning. Automated applications and AI-written outreach now flood applicant pools and inboxes, so candidates struggle to be noticed and employers struggle to tell who is serious. Companies have long paid recruiters to represent them in the market; job seekers have rarely had anyone working on their side. Co-founder and CTO Saaras Mehan argues that more applications and sharper filters will not fix this, and that the market needs agents which understand what both sides actually want.
The company runs two agents. Jack works for candidates, holding voice calls much as a career coach would: benchmarking pay, talking through a dreaded counteroffer and scanning millions of open roles for the handful worth their time. People tell Jack things a CV never captures, from the manager they want to leave to the problem they would take a pay cut to work on. Jill works for employers, studying the job description and the business and asking what success in the role looks like, then recruiting from Jack's network. When both agents agree on a fit, the candidate is introduced straight to the hiring manager, with no application in between. The model resembles an executive search firm, with a far wider network and lower fees.
Mehan founded the company in March 2025 with chief executive Matt Wilson, who previously co-founded employer-of-record business Omnipresent, sold to Deel in 2025. Since its $20M seed round led by Creandum in October 2025, Jack's network has grown tenfold to 350,000 people, and Jill has worked with 5,000 businesses, mostly fast-growing startups such as Ramp, Attio, Multiverse and Fyxer. Between them the agents have arranged 25,000 interviews without a single application and now set up around 5,000 a month. Revenue is up 40-fold over the same period. Some US outlets reported the new round as $40M.
New investors Madrona and Antler joined the round, alongside existing backers Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc. The money will fund expansion across the US, following launches in San Francisco in January and New York in June, where nearly four times as many interviews were completed as in London over the same period after launch. Air Street general partner Nathan Benaich said the firm backed Wilson and Mehan because they are rebuilding the hiring market rather than building another tool to search it.
Sources