Jack & Jill Raises $40 Million to Skip the Job Application

Jack & Jill, a London startup that pairs job seekers and employers with competing AI agents instead of a job application, raised $40 million in a Series A round led by Air Street Capital, the company said Sept. 15, ten months after a $20 million seed round in October 2025. Neither round has come with a disclosed valuation.

Madrona and Antler joined as new investors, alongside existing backers Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc. The round brings Jack & Jill's total funding to $60 million.

What Jack does, and what Jill does

Jack is an AI voice agent that talks to a job seeker by phone, email and WhatsApp to learn what they want from their next role. Jill is a separate agent that reads a company's job description and interrogates what success in the role actually looks like. When both agents conclude a match is worth making, the candidate is introduced directly to the hiring manager, and no application is filed. Chief Executive and co-founder Matt Wilson previously co-founded Omnipresent, an employer-of-record company that Deel acquired in 2025; Saaras Mehan, the other co-founder, serves as chief technology officer.

Two different user counts

Jack & Jill's own announcement says 380,000 people in San Francisco, New York and London use Jack. Pulse2's independent reporting puts the number at approximately 350,000, a gap of roughly 30,000 users between the company's account and outside reporting on the same round. Pulse2 also reported that San Francisco and New York together generated nearly four times as many interviews as London over a comparable period, and that revenue rose roughly 40-fold since the October seed round, a multiple that says nothing about the base revenue it was multiplying.

1. Seed (Oct. 2025)20 $ millions
2. Series A (Sept. 2026)40 $ millions

Source: Jack & Jill company blog and Pulse2, accessed 2026-09-24

A 25-person company arranging 5,000 interviews a month

According to Pulse2's reporting, Jack & Jill employs 25 people, 15 of whom are former startup founders themselves, and the platform is now arranging roughly 5,000 interviews a month without a single job application behind any of them. Users have spent a combined 12,000 hours in conversation with the Jack agent since launch; one user, Pulse2 reported, logged 144 calls totaling about 44 hours. Wilson's pitch to investors rests on that volume of conversation functioning as proprietary data neither a job board nor a traditional applicant-tracking system collects.

What the round does not say

Jack & Jill's blog post does not break down how the $40 million will be split between expanding to new cities and improving the agents themselves, and it does not say whether the company is profitable at its current interview volume. The clearest test ahead is geographic: whether Jack & Jill can close the gap between its strong San Francisco and New York numbers and its comparatively quiet London market, in the city where the company is headquartered. Jack & Jill's structure resembles Ema's $77 million Series B, another AI-agent company that raised a large round without naming a valuation, and it sits in the same funding wave as Raindrop's Series A for monitoring AI agents, a sign investors are now funding both the agents doing the work and the tools built to check on them.