London AI recruitment company Jack & Jill has raised £30m in a round led by Air Street Capital, roughly eleven months after announcing a $20m seed led by Creandum. The round's stage, post-money valuation and dilution were not disclosed.
Jack & Jill builds conversational AI agents that sit on both sides of the hiring process — one working for the candidate, one for the employer — and match the two. The company was founded in 2025 by a team including Matthew Wilson and came out of Entrepreneur First, the London talent investor.
The new money is led by Air Street Capital, the London firm founded by Nathan Benaich that invests exclusively in AI-first companies. It is Air Street's first disclosed position in the business, and it arrives as a new lead rather than as a follow-on from the existing register.
That matters for the cap table. Jack & Jill's $20m seed, announced in October 2025, was led by Creandum with Entrepreneur First participating alongside a group of operator angels. A £30m round led by a different firm typically resets pricing and board composition, and installs a second institutional voice above the seed holders unless they have taken their full pro-rata.
Neither the company nor the investors disclosed a valuation, the split between primary and secondary, or whether any early shareholders sold down. Terms were not disclosed.
The pace is the striking figure. Jack & Jill has moved from formation in 2025 to roughly £45m of disclosed equity in under two years, raising a round more than twice the size of its seed inside a year of announcing it. Companies raise on that cadence when either revenue or competitive pressure is moving faster than the original plan assumed.
Both apply in AI recruitment. The category has attracted heavy funding on the argument that hiring is a large, badly served market where language models can do genuine work rather than decorate an existing workflow. It has also drawn well-capitalised competitors on both sides of the Atlantic, which raises the cost of standing still.
The strategic logic of an Air Street lead is specialisation. A generalist growth fund brings capital; a dedicated AI investor brings a view on model economics, inference costs and where a wrapper stops being a wrapper. For a company whose product margin depends directly on token spend, that distinction is not cosmetic.
What the round does not yet answer is scale of commercial traction. Jack & Jill has not published revenue, placement volumes or enterprise customer counts, and none accompanied this raise. Until they arrive, the £30m is a bet on the team and the category rather than on disclosed unit economics.
For London, it is another data point in a pattern the city has been building all year: AI companies founded here raising second rounds domestically, with a British lead, instead of moving the cap table to the United States at Series A.
Original source: Sifted — https://sifted.eu/articles/exclusive-jack-jill-30m/
