Jack & Jill raises £30m led by Air Street Capital with Madrona
This article covers Jack & Jill, an AI startup, which has raised £30m in a series A funding round to expand its two-agent hiring marketplace that runs AI agents on both sides of the job market. The funding aims to support US expansion and scale a platform that brokers introductions between candidates and employers, affecting startups, recruiters and jobseekers in the hiring market.
Jack & Jill, an AI startup, has raised £30 million in a series A funding round to expand its two-agent hiring marketplace that connects candidates and employers by running AI agents on both sides of the job market. The funding marks a step-up for the company as it targets US expansion after launches in San Francisco and New York, and reflects growing investor interest in AI-driven labour-market tools.
Why it matters
The hiring market is noisy: automated applications and outreach flood employer inboxes while candidates struggle to surface their true fit. Jack & Jill’s approach — pairing an AI agent for the candidate (Jack) with one for the employer (Jill) and only making introductions when both sides signal interest — aims to reduce wasted time for both parties. If the model scales, it could change how hiring pipelines form and how passive candidate pools are activated without relying on resumes alone.
Inside the product
The product places two distinct AI agents on opposite sides of hiring. Jack acts like a career coach for candidates, running voice conversations, benchmarking pay expectations, helping with negotiation scenarios and searching millions of live job postings to surface a small number of highly relevant roles. Candidates share contextual signals with Jack that do not typically appear on resumes, such as a problematic manager or the types of problems they would accept a pay cut to solve.
Jill works for employers. She reads job descriptions, researches the business, clarifies what success in a role looks like and then recruits from Jack’s network. When both agents agree there is a match, the candidate is introduced directly to the hiring manager rather than completing a standard application.
Since its seed round, Jack & Jill says Jack’s network has grown tenfold to 350,000 people and the team has recorded 12,000 hours of candidate conversations in recent months, with one person calling 144 times. Jill has been used by around 5,000 businesses, including fast-growing startups such as Ramp, Attio, Multiverse, Tavus, Faculty, Fyxer and Corgi — a mix of fintech, productivity and AI consultancies that illustrate the platform’s early traction among growth-focused employers. Together the agents have arranged 25,000 interviews without an application and now arrange a further 5,000 each month. The company also reports revenue has increased 40-fold since the seed round.
Who are the investors?
The round was led by Air Street Capital, with participation from new investors Madrona and Antler. Existing backers Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc also joined, alongside additional investors Dig Ventures, Firedrop, Episode 1 and Playfair.
In the announcement, 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. 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.
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Founder perspective
Jack & Jill was founded in March 2025 by Matt Wilson and Saaras Mehan and now employs 25 people across London and San Francisco, with 15 of those hires coming from founder backgrounds. Wilson is a third-time founder who co-founded and co-led Omnipresent, an employer-of-record business sold to Deel in 2025. Mehan previously co-founded Kular and represented England in chess.
In the announcement, Saaras Mehan, Co-founder & CTO at Jack & Jill, said:
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.
In the announcement, Matt Wilson, Co-founder & CEO at Jack & Jill, said:
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.
Customer feedback is already positive. In the announcement, Archie Hollingsworth, Co-founder at Fyxer, said:
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.
The bigger picture
Jack & Jill’s raise joins a string of AI hires-and-marketplace plays attracting capital as founders explore interventions that reduce friction in hiring. The company’s move to scale in San Francisco and New York follows an often-seen pattern for UK-founded startups that validate in London before prioritising US markets; Jack & Jill reports nearly four times as many interviews were completed in those US cities as in London after launch.
The deal also signals continuing appetite from AI investors for companies that combine conversational AI with network effects rather than pure search optimisation. How regulators, employers and jobseekers respond to agent-mediated introductions will shape whether this model becomes a mainstream alternative to applicant-tracking systems or remains a niche route for select roles.
For the UK and wider European ecosystem, the round highlights export ambitions among local AI startups and underlines ongoing investor support for companies that aim to rewire labour-market infrastructure.
They've invested in Jack & Jill
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| Investors | Investment Focus | Startup Investments | Round Size | Connect |
|---|---|---|---|---|
 Air Street Capital( ) Air Street Capital is a venture capital firm specialising in AI-first companies.... London  | ||||
 Madrona Ventures( ) Seattle, US  | ||||
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 Ada Ventures( ) This venture capital firm focuses on three key investment areas: Climate Equity,... London | ||||
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 Expedite Capital( ) | ||||
 Repeat.vc( ) | ||||
 Dig Ventures( ) This European venture capital firm focuses on early-stage investments in B2B Saa... London | ||||
 firedrop( ) London | AlphaJack & Jill | |||
 Episode 1 Ventures( ) The firm specialises in investing in Pre-Seed and Seed stage B2B software compan... London | ||||
 Playfair Capital( ) The venture capital firm focuses on providing an unfair advantage to founders, s... London | ||||
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