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.
Why it matters
- What it limits 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.
- Who has to decide decision The spending decision is US-first, so the London operation gets the smaller share of a round raised by a London-founded company.
- Who's exposed 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.
- What doesn't add up 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.
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Twelve thousand hours of talking to Jack, spread across a network of 350,000 professionals, is roughly two minutes a head [22]. One user called 144 times [17]. That distribution matters because Jill sources candidates from Jack's network instead of an open applicant pool [8], 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 [18][6], five per client [25]. 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 [26].
The company did not disclose a valuation, or the revenue base that grew 40-fold since the October 2025 seed [10][3]. 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" [12].
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 [20]. The same report puts the global recruitment software market at $3.4 billion in 2025 and $7.5 billion by 2034 [30], compounding at about 9% a year [28], and notes that other research firms give markedly different estimates [30].
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 [14]. The sale was 2.5% of the peak mark [23]. 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 [24].
Most of the new money goes to the United States, after the January San Francisco launch and the June one in New York [4], and the two US cities have already produced nearly four times London's interview count over the same post-launch period [19]. So London is where the expansion budget is not going, for a 25-person team still split across both [11].
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% [27]. 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" [13]. 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" [29]. Mercor's $2 billion mark says investors will currently pay more for the single-sided version [20].
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.
Information, not investment advice. This story is general information about companies and markets, drawn from cited reporting. It is not a recommendation to buy, sell or hold any security; check the cited sources before acting.
Clarity's read
What the record supports and how the coverage leans. The claims behind it follow.
Reality
- Evidence38
- Adoption42
- Hype gap+34
- Incentives78
- Confidence62
Perspective Coverage
3 publishers- Builder
- Builder 27%
- Operator
- Operator 23%
- Investor
- Investor 50%
Claim ledger
Ranked by verification strength, evidence, and original report placement.
- [1]
Jack & Jill raised EUR 34.68 million ($40 million) in a Series A led by Air Street Capital, with new investors Madrona and Antler joining.
- [2]
TheSaaSNews records the funding date of the $40 million Series A as September 15, 2026.
- [3]
The Series A brings total funding to EUR 52.9 million ($60 million), following a EUR 18.3 million ($20 million) seed round in October 2025 led by Creandum and backed by more than 75 angel investors.
- [4]
The new capital will primarily fund expansion across the US, building on the January launch in San Francisco and the June launch in New York.
- [5]
Existing backers Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc joined the round, alongside current investors Dig Ventures, Firedrop, Episode 1 and Playfair.
- [6]
Jack & Jill was founded in March 2025 by Matt Wilson and Saaras Mehan.
- [7]
Jack acts for job seekers, holding voice conversations that function more like career-coaching sessions than typical job-search chatbots, and uses those conversations plus a daily scan of millions of open roles to work out what a candidate wants.
- [8]
Jill works for employers: she reads job descriptions, researches the hiring company, asks what success looks like, and sources candidates directly from Jack's network rather than from an open applicant pool; when both agents agree on a match the candidate and employer are introduced directly, with no application required.
- [9]
The company says its network has grown tenfold since the seed round to 350,000 professionals, while Jill has now worked with 5,000 businesses, including Ramp, Attio, Multiverse and Corgi.
- [10]
Revenue has grown 40-fold since the seed round.
- [11]
The company employs 25 people across London and San Francisco, 15 of whom are former founders.
- [12]
"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," said Nathan Benaich, General Partner at Air Street Capital.
- [13]
"Candidates struggle to be seen, while employers cannot tell who is serious. More applications and better filters will not solve that. It requires a fundamentally different solution: a marketplace brokered by agents that understand what both sides want," said Saaras Mehan, co-founder and CTO.
- [14]
Matt Wilson co-founded the employer-of-record company Omnipresent in 2019 and took it to a $600 million valuation before it was acquired by Deel in October 2025 for $15 million, according to Dealroom.
- [15]
TechFundingNews lists Jill's clients as Ramp, Attio and Fyxer.
- [16]
Mehan co-founded Kular (YC W22) and is a former England chess international.
- [17]
The company says people have logged 12,000 hours talking to Jack in the past few months, with one user calling 144 times.
- [18]
Together the two agents have arranged 25,000 interviews and are now facilitating 5,000 more each month.
- [19]
Jack & Jill has completed nearly four times as many interviews across San Francisco and New York as in London over the same post-launch period.
- [20]
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 tool; smaller firms such as AINA are pursuing similar concepts.
- [21]
TechFundingNews wrote that Wilson is "now seeking from investors four times the amount paid when the company was acquired", with the aim of providing a hiring agent for a billion people by 2030.
- [22]
12,000 hours of Jack conversations across a network of 350,000 professionals averages about two minutes per member.
- [23]
Deel's $15 million purchase price for Omnipresent was 2.5% of the company's $600 million peak valuation.
- [24]
The $40 million Series A is about 2.7 times the $15 million Deel paid for Omnipresent, while the $60 million raised in total is four times it.
- [25]
25,000 interviews arranged across 5,000 client businesses is five interviews per client.
- [26]
At 5,000 interviews a month, the current monthly rate is one fifth of the 25,000 arranged to date, so five months at that pace doubles the cumulative total.
- [27]
5,000 interviews a month against a network of 350,000 professionals is about 1.4% of members per month.
- [28]
Growth from $3.4 billion in 2025 to $7.5 billion by 2034 is about 9% a year compounded.
- [29]
Wilson, co-founder and CEO, said: "By 2030, a billion people will have an AI agent searching every opportunity on their behalf and deciding which ones deserve their attention. Every company will have one helping it hire."
- [30]
The global recruitment software market was worth $3.4 billion in 2025 and is expected to reach $7.5 billion by 2034, while other research firms provide markedly different estimates.
Sources
3 independent publishers whose own reporting we read for this story.
- eu-startups.comLondon-based Jack & Jill raises €34.68 million Series A to scale its AI agents for jobseekers and employers | EU-Startups
1 article · September 15, 2026
- techfundingnews.comAir Street Capital leads $40M Series A into Jack & Jill’s dual-agent hiring marketplace
1 article · September 15, 2026
- thesaasnews.comJack & Jill Raises $40M Series A
1 article · September 15, 2026