Jack & Jill raises £30M Series A to put an AI agent on both sides of every hire

Jack & Jill (London) has raised £30 million (approximately €34.7 million) in a Series A led by Air Street Capital, with new investors Madrona and Antler joining, alongside a broad syndicate of existing backers including Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital, Repeat.vc, Dig Ventures, Firedrop, Episode 1, and Playfair. The company, founded in March 2025 by Matt Wilson (CEO) and Saaras Mehan (CTO), runs two AI agents that sit on opposite sides of the hiring process.

The round brings total funding to approximately €52.9 million ($60 million), following a €18.3 million Seed in October 2025. The company has now arranged more than 25,000 interviews between candidates and hiring managers, with around 5,000 per month.

How the system works

The premise is structural: conventional hiring is adversarial. Candidates write CVs to pass keyword filters; employers post job descriptions to limit applications rather than describe the role; both sides invest time they cannot recover on interactions they would not have chosen with better information. The job board model amplifies this by optimising for volume.

Jack & Jill's architecture inverts it. Jack — the candidate-side agent — engages through voice calls, email, and WhatsApp, learning what the candidate actually wants (not what looks good on a CV), what they are willing to move on, and what they will walk away from. Jill — the employer-side agent — interrogates the hiring manager about what the role actually requires, not what the job description says. A match is made only when both agents agree that the introduction is worth making. The candidate is then introduced directly to the hiring manager, bypassing the application layer entirely.

The numbers Matt Wilson and Saaras Mehan have built: 350,000 professionals in the network, 5,000 businesses on Jill. Founders Wilson and Mehan bring operational specificity: Wilson co-founded Omnipresent (acquired by Deel in 2025), a company that proved employers will buy infrastructure they cannot see when it solves a real workflow problem. Mehan co-founded Kular (YC W22, AI outbound sales) and is a former England chess international — a background in optimising games with incomplete information that maps more directly to two-sided matching than it might appear.

The investor logic

Nathan Benaich, Air Street Capital: "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."

Air Street Capital's thesis is concentrated on research-grade AI applications; its portfolio includes companies building in AI safety, medical imaging, and drug discovery — contexts where matching quality, not throughput, defines the product. That framing is coherent for Jack & Jill's architecture: the system adds value precisely by reducing the volume of interactions, not by increasing it.

Madrona's entry is significant for US distribution: the Seattle-based firm has backed developer-tooling and enterprise SaaS companies with strong US market penetration and is a credible route-to-market partner for the US expansion that is consuming most of this round's capital. The company launched in San Francisco in January 2026 and in New York in June; the $40 million is the fuel for that build-out.

The competitive landscape is not empty — Paradox, HireVue, Findem, and a cohort of newer agentic recruiting startups are all building toward variations of the same thesis. What differentiates Jack & Jill's position at this stage is the two-sided symmetry: most incumbents have an agent on one side (screening candidates or parsing JDs) but not both simultaneously. Whether that symmetry is the durable moat, or a feature that can be copied, is the Series B question.