Invest3 publishers3 min readPublished
Jack & Jill raises 2.7 times what Deel paid for its co-founder's last company
Air Street Capital led $40 million into a hiring marketplace where an agent for the candidate and an agent for the employer must both agree before an introduction happens. The two have arranged 25,000 interviews so far.
The Investor · Invest desk
What happened
- Jack & Jill raised EUR 34.68 million, or $40 million, in a Series A led by Air Street Capital, with Madrona and Antler joining as new investors alongside existing backers including Creandum.
- The round takes total funding to $60 million, following a $20 million seed in October 2025 that was led by Creandum and backed by more than 75 angel investors.
- Jill reads job descriptions and sources candidates from Jack's network, and when both agents agree on a match the candidate and employer are introduced directly with no application.
- The two agents have arranged 25,000 interviews to date and are now facilitating 5,000 more each month, with the candidate network up tenfold since the seed to 350,000 people.
Compiled by The InvestorSomething wrong?How this is made
Why it matters
- constraint Because Jill can only introduce people Jack has already spoken to, employer coverage is capped by candidate supply, and five interviews per client to date is what that pairing has yielded.
- decision The spending decision is US-first, so the London operation gets the smaller share of a round raised by a London-founded company.
- exposure A $40 million round leaves Jack & Jill competing for the same employer budgets as a rival carrying a $2 billion mark on the single-sided version of the product.
- contradiction TechFundingNews cites a recruitment software market of $3.4 billion rising to $7.5 billion while flagging that other researchers size it very differently, so the addressable market cannot anchor this round's price.
Twelve thousand hours of talking to Jack, spread across a network of 350,000 professionals, is roughly two minutes a head [1]. One user called 144 times [8]. That distribution matters because Jill sources candidates from Jack's network instead of an open applicant pool [7], so the depth of those calls is what an employer is actually buying.
On the employer side the counting is easier. Jill has worked with 5,000 businesses, among them Ramp, Attio and Multiverse [9], and the two agents have arranged 25,000 interviews since the company was founded in March 2025 [10][5], five per client [4]. The current rate of 5,000 a month is a fifth of everything arranged to date, so five more months at that pace doubles the total [5].
The company did not disclose a valuation, or the revenue base that grew 40-fold since the October 2025 seed [11][4]. Nathan Benaich, general partner at Air Street Capital, said: "The next leap in hiring will not come from better searches over the same resumes or more automated outreach. It will come from putting an agent on both sides of the table and making the introduction only when both sides would take the call" [15].
Nearby, Mercor has raised $100 million at a $2 billion valuation for AI-driven technical interviews and Juicebox $30 million for its PeopleGPT search tool, according to TechFundingNews [19]. The same report puts the global recruitment software market at $3.4 billion in 2025 and $7.5 billion by 2034 [20], compounding at about 9% a year [7], and notes that other research firms give markedly different estimates [20].
Matt Wilson co-founded Omnipresent in 2019 and took it to a $600 million valuation before Deel acquired it in October 2025 for $15 million, according to Dealroom figures cited by TechFundingNews [18]. The sale was 2.5% of the peak mark [2]. That report says he is "now seeking from investors four times the amount paid when the company was acquired" [21]; this round is 2.7 times $15 million, and it is the $60 million raised since founding that gets to four [3].
Most of the new money goes to the United States, after the January San Francisco launch and the June one in New York [13], and the two US cities have already produced nearly four times London's interview count over the same post-launch period [12]. So London is where the expansion budget is not going, for a 25-person team still split across both [14].
This is a supply-side bet, and the number to test it on is introductions per member: 5,000 a month against 350,000 people is about 1.4% [6]. If the network multiplies tenfold again and the monthly interview count does not, the voice calls will have produced a list, and resume filtering is a cheaper way to sell a list. Saaras Mehan, co-founder and CTO, said the problem "requires a fundamentally different solution: a marketplace brokered by agents that understand what both sides want" [16]. Wilson said, "By 2030, a billion people will have an AI agent searching every opportunity on their behalf and deciding which ones deserve their attention" [17]. Mercor's $2 billion mark says investors will currently pay more for the single-sided version [19].
What to watch
- Any disclosed valuation or absolute revenue number, which would let the 40-fold growth be checked against a level.
- Mercor's next raise at or above its $2 billion mark, pricing single-sided interviewing against the dual-agent structure.
- Whether the 5,000-a-month interview rate keeps climbing once the US expansion spending lands.