Jack & Jill raises $40M to put an AI agent on both sides of hiring

Jack & Jill, a London startup, has raised a $40M — about £30M — Series A to build out a distinctive idea about how hiring should work: give both sides an AI agent and let the agents do the matching. “Jack” is an agent that works for a jobseeker, learning their career and putting them forward for roles; “Jill” is an agent that works for an employer, sourcing and screening candidates. The company describes the result as making warm introductions at the scale of the internet. The round was led by Air Street Capital, and the company says its revenue has grown roughly fortyfold in the ten months since it raised a seed.

It is a deliberately different bet from most AI-recruitment tools, which tend to be a single system bolted onto one side — a résumé screener for employers, or a job-matcher for candidates. Jack & Jill’s premise is that the interesting thing happens when both sides are represented by an agent, each acting in its principal’s interest, meeting in the middle. Whether that produces better matches or simply an arms race of agents talking to agents is the open question, but it is a genuinely novel structure for a market that has resisted improvement for a long time.

The people and the money behind it are worth noting. It was founded in March 2025 by Matt Wilson, who previously sold his company Omnipresent to the payroll firm Deel, and Saaras Mehan, who earlier founded the Y Combinator-backed AI sales startup Kular — repeat founders, in other words, who have built and sold before. The Series A was led by Air Street Capital, the London firm run by Nathan Benaich that specialises in AI, with Madrona, Antler, Creandum and Entrepreneur First among the other backers. That is a serious cap table for a company not yet two years old.

For the UK, it is another data point in a pattern we keep seeing: London producing agentic-AI companies aimed squarely at real, unglamorous workflows — after precision manufacturing and enterprise AI governance, now recruitment — and increasingly backed by home-grown AI-specialist investors rather than only American ones. The caution is the one that shadows all automated hiring: when every CV is written and every applicant screened by an agent, the risk is that the process gets faster and noisier without getting fairer, and questions of bias and gaming do not disappear just because an agent is doing the work. Jack & Jill’s bet is that representation on both sides is part of the answer. It is a bet worth watching.