Jack & Jill raises $40M Series A for its AI hiring agents

Jack & Jill, the London startup whose paired voice agents sit on both sides of the job interview, has raised a $40M Series A led by Air Street Capital, with Madrona and Antler joining, to push its AI hiring marketplace deeper into the US.

Hiring is one of the few markets everyone agrees is broken – hundreds of applications per role, CVs nobody reads, recruiters swamped on both sides. And yet one of the fastest-scaling answers to it is being built in London, by a team of 25 that is already outgrowing its home market. Below, I lay out the round, what the company actually does, and why the interesting number here is not the $40M.

Ten months from a $20M seed to a $40M Series A

Jack & Jill announced a $40M Series A on 15 September 2026, led by Air Street Capital, the London firm run by Nathan Benaich. Madrona and Antler come in as new investors, and the seed syndicate returns: Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc, with EU-Startups also listing Dig Ventures, Firedrop, Episode 1 and Playfair in the round.

The money goes to US expansion. The company launched in San Francisco in January 2026 and New York in June 2026, and the new capital builds on both, per the announcement. It lands just ten months after a $20M seed led by Creandum in October 2025, taking the total raised to $60M for a company founded in March 2025 – eighteen months from incorporation to $60M on the cap table.

“The next leap in hiring will not come from better searches over the same resumes or more automated outreach,” Benaich said in the announcement – it comes, in his framing, from putting an agent on both sides of the table.

Jack talks to candidates, Jill talks to employers

The product is two voice agents. Jack holds phone conversations with jobseekers – career history, ambitions, constraints – and coaches them along the way. Jill does the equivalent with hiring managers, working out what a role actually needs. When the two agents agree there is a fit, the humans get a direct introduction: no job ad, no application form, no keyword-matched CV pile.

Founders Matt Wilson and Saaras Mehan are second-time operators. Wilson founded the employer-of-record company Omnipresent in 2019 and sold it to Deel in October 2025; Mehan co-founded Kular, a Y Combinator-backed AI sales startup. Of the 25 people on the team, 15 are former founders – an unusually dense bench for a Series A company.

The traction figures, all from the company’s announcement: a candidate network of 350,000 professionals, ten times where it stood at the seed; 5,000 businesses using Jill, including Ramp, Attio and Multiverse; 25,000 interviews arranged so far, with 5,000 more added each month; and revenue up 40x since the seed round. Announced figures rather than audited ones, as always at this stage – but the direction is hard to argue with.

A $639bn services market with a $600M software shadow

The market sizing here is a tale of two numbers. The software category Jack & Jill nominally sits in is small: AI recruitment software was worth $601.5M globally in 2025, forecast to grow at a 7.53% CAGR from 2026 to 2034 (Straits Research, August 2026). The market it is actually priced against is enormous: global staffing revenue reached $639bn in 2025, up 2% year on year (Staffing Industry Analysts, 2026). Agents that conduct the interview themselves compete with recruiters’ fees, not with applicant-tracking licences – and that gap between the two numbers is the whole investment thesis.

For scale against our own records: this is the third round we have covered today, and by far the largest Series A – Veridion’s $20M Series A this morning and Chift’s €10.5M last week both sit well below it. The pattern of AI companies raising to replace services revenue rather than sell software also echoes Limetax’s €36M raise to build an AI-powered group of German tax firms, covered here last week.

What 4x US interview volume says about where this goes

So why does a London company raise a round like this to leave for the US? The uncomfortable part first: EU-Startups reports the US markets are already producing nearly four times the interview volume of London. Employers there adopt faster and pay faster, and Jack & Jill is following its own data – the good news is that the product, the engineering and the cap table remain anchored in Europe, with Air Street, Creandum, Ada Ventures and Entrepreneurs First all holding meaningful positions in what may become the defining company of agentic hiring.

What we are seeing, across this round and the wider European fundraising data, is a repeatable shape: repeat founders, a voice-agent product, revenue multiplying inside a year, and a round sized off a services market rather than a software category. What to watch from here is whether candidates keep trusting an agent with their career conversations at ten times today’s volume, and whether the fee per placement holds anywhere near recruiter level as the network grows – those two curves, not the headline number, will decide how big this gets.

Europe keeps producing the founders; increasingly it also produces the lead cheques. Keep an eye on the Jack & Jill startup record as this one compounds – the interview counter will tell the story faster than the press releases do.