Air Street Capital leads $40M Series A into Jack & Jill’s dual-agent hiring marketplace

• The AI recruiting platform Jack & Jill has obtained $40 million in its Sequence A funding spherical, with Air Road Capital appearing because the lead investor.
• A $20 million seed spherical came about ten months in the past, bringing the corporate’s complete funding to $60 million.
• Matt Wilson, a co-founder, beforehand offered his closing startup, Omnipresent, to Deel for a reported $15 million.

The AI recruiting platform Jack & Jill, based mostly in London, simply raised $40 million in a Sequence A funding spherical, led by Air Road Capital, with Madrona and Antler becoming a member of as new buyers, whereas Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital, and Repeat.vc had been among the many earlier buyers.

This financing comes after Jack & Jill raised $20 million in its seed spherical ten months in the past, bringing the entire quantity raised thus far to $60 million. The corporate states that its candidate community has elevated tenfold to 350,000 individuals.

“The following leap in hiring is not going to come from higher searches over the identical resumes or extra automated outreach. It is going to come from placing an agent on each side of the desk and making the introduction solely when each side would take the decision,” mentioned Nathan Benaich, a common associate at Air Road Capital, a agency that has beforehand invested in Synthesia and Wayve.

In a aggressive job-hiring surroundings the place candidates can use AI to ship out lots of of functions on daily basis whereas employers can reject them simply as swiftly, belief fails on each side.

“Candidates wrestle to be seen, whereas employers can not inform who’s severe. Extra functions and higher filters is not going to resolve that. It requires a basically completely different resolution: a market brokered by brokers that perceive what each side need,” added Saaras Mehan, co-founder and chief know-how officer.

A founder’s second chapter

Matt Wilson co-founded Omnipresent, an employer-of-record firm, in 2019 and took it to a $600 million valuation earlier than it was acquired by Deel in October 2025 for $15 million, in keeping with Dealroom.

Ten months on, he’s now looking for from buyers 4 instances the quantity paid when the corporate was acquired, with the purpose of constructing an organization with a a lot bigger goal: to supply a hiring agent for a billion individuals by 2030.

Mehan, who can be a co-founder, had earlier based Kular, an AI gross sales startup that obtained funding from Y Combinator, and had at one time performed chess for England earlier than getting into the recruitment discipline.

The truth that this partnership combines an individual who offered an organization at a worth under market expectations with an engineer famend for his strategic pondering underscores the background of this financing.

How Jack and Jill work in observe

Jack conducts phone interviews with candidates to study their job preferences, gathering insights that Mehan believes databases or scrapers can not seize. Jill conducts related interviews with hiring managers after which matches candidates with employers based mostly on these conversations somewhat than on key phrase matches alone.

When each brokers agree {that a} match has been made, the candidate is given a direct introduction to the hiring supervisor, bypassing the conventional utility process.

Jack & Jill at the moment are working in a aggressive surroundings. Mercor has raised $100 million at a $2 billion valuation for its AI-driven technical interviews; Juicebox has secured $30 million for its PeopleGPT search software; and smaller companies akin to AINA are also pursuing similar concepts.

Whereas most opponents concentrate on enhancing resume filtering, Jack & Jill believes that resumes shouldn’t be the start line and that voice conversations present distinctive insights. It stays an open query whether or not this method will be scaled to serve greater than 5,000 firms with out merely changing into yet one more database.

The cash, the expansion, and the open questions

The cash it has obtained shall be used to fund its growth in the USA, following launches in San Francisco in January and in New York in June. Because the seed financing spherical, Jack & Jill has seen its income improve by forty instances. The corporate’s workforce of 25, based mostly in London and San Francisco, consists of 15 former founders.

On the shoppers’ aspect, Jill has handled 5,000 firms, together with Ramp, Attio and Fyxer.

The global recruitment software market was worth $3.4 billion in 2025 and is anticipated to succeed in $7.5 billion by 2034, whereas different analysis companies present markedly completely different estimates, underscoring the uncertainty across the market dimension.

It’s clear that if Jack & Jill’s agent-matching mannequin fails to beat out conventional recruiters and job boards, it would come underneath shut examination. Wilson is already conscious of the difficulties concerned in having to promote the enterprise for lower than anticipated.

The present funding spherical will point out whether or not buyers see his expertise as having made him a greater founder or merely extra decided.

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