Jack & Jill, a startup that puts AI agents on both sides of the job market, has raised £30 million in a Series A led by Air Street Capital, with participation from new investors Madrona and Antler. Existing investors Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc also participated. Other investors in the company include Dig Ventures, Firedrop, Episode 1 and Playfair.
Two agents sit either side of the hiring process. Jack works for the person looking for their next role, speaking to them on voice calls as a career coach would, benchmarking what they should be earning, talking them through the counteroffer they are dreading and searching millions of open job postings for the few opportunities they will care about. Candidates tell Jack things that never reach a resume: the manager they are trying to get away from, or the kind of problem they would take a pay cut to work on. Jill works for the employer, reading the job description, researching the business and asking questions to understand what success in the role looks like, then recruiting from Jack's network. When both agents agree a candidate and a role are a strong match, the person is introduced directly to the hiring manager instead of filling in an application. The service works much like an executive recruiter, with a larger network and lower costs.
Jack's network has grown tenfold to 350,000 people since the seed round, and they have spent 12,000 hours talking to him about their careers in the past few months alone, with one person calling 144 times. Jill has worked with 5,000 businesses, mostly fast-growing startups including Ramp, Attio, Multiverse, Tavus, Faculty, Fyxer and Corgi. Together the agents have arranged 25,000 interviews without a candidate submitting an application, and now arrange another 5,000 each month. Revenue has increased 40-fold since the seed round.
Founded in March 2025 by Matt Wilson and Saaras Mehan, Jack & Jill employs 25 people across London and San Francisco, 15 of them former founders. Wilson is a third-time founder who co-founded and co-led Omnipresent, the employer-of-record business sold to Deel in 2025. Mehan previously co-founded Kular and is a former England chess international.
The new funding will help Jack & Jill grow across the United States, following launches in San Francisco in January and New York in June. Nearly four times as many interviews were completed across San Francisco and New York as in London over the same period after launch.
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. Hundreds of thousands of people have told Jack, in their own words, what they want from their careers. No database contains that information and nobody can scrape it. We led this round because Matt and Saaras are rebuilding the market rather than building another tool to search it.
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.
Every company has someone paid to represent its interests in the job market. People have never had the same for their careers. 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.
Jill gives us exactly what we need. Direct introductions to people we want to hire, not another shortlist. Within minutes of briefing her on a role, I have meetings with strong candidates in my calendar.
