London-based Jack & Jill raises €34.68 million Series A to scale its AI agents for jobseekers and employers

Jack & Jill, the London-based startup that puts an AI agent on each side of the hiring table, has raised €34.68 million ($40 million) in a Series A round.

The round was led by Air Street Capital, with new investors Madrona and Antler joining. Existing backers Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc also joined the round, alongside current investors Dig Ventures, Firedrop, Episode 1 and Playfair.

“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.

Founded in March 2025 by Matt Wilson and Saaras Mehan, Jack & Jill runs two AI agents that sit on opposite sides of the hiring process. Jack acts on behalf of job seekers, holding voice conversations that function more like career-coaching sessions than typical job-search chatbots.

The company says people have logged 12,000 hours talking to Jack in the past few months, with one user calling 144 times. Jack uses those conversations, along with a daily scan of millions of open roles, to work out what a candidate actually wants, including details that would never appear on a resume, such as a difficult manager or a desired salary.

Jill, on the other hand, works for employers. She reads job descriptions, researches the hiring company, and asks questions to understand what success in the role looks like, then sources candidates directly from Jack’s network rather than from an open applicant pool. When both agents agree that a candidate and a role are a match, the two are introduced directly to each other, with no application required.

“AI is displacing jobs and pushing more people into the job market. At the same time, automated applications and outreach are flooding inboxes and applicant pools. 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 Mehan, co-founder and CTO of Jack & Jill.

Before starting Jack & Jill, Wilson co-founded and co-led the employer-of-record company Omnipresent, which was acquired by Deel in 2025, while Mehan co-founded Kular (YC W22) and is a former England chess international. The company employs 25 people across London and San Francisco, 15 of whom are former founders.

The Series A brings Jack & Jill’s total funding to €52.9 million ($60 million), following a €18.3 million ($20 million) Seed round in October 2025. That round was led by Creandum and backed by more than 75 angel investors, including 2016 Formula One World Champion Nico Rosberg and individuals connected to Lovable, Anthropic and ElevenLabs.

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. Together, the two agents have arranged 25,000 interviews and are now facilitating 5,000 more each month.

Jack & Jill has seen faster traction since its launch in the US than in London. The company has completed nearly four times as many interviews across San Francisco and New York over the same post-launch period, while revenue has grown 40-fold since the Seed round.

Wilson, co-founder and CEO of Jack & Jill, 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. Connecting those agents will make the job market run like clockwork and uncover opportunities on both sides that would otherwise be missed.”

The new capital will primarily fund Jack & Jill’s expansion across the US, building on its January launch in San Francisco and June launch in New York.