AI Agents Are Rewriting the Hiring Playbook: Inside Jack & Jill's $40M Bet

Jan de Vries · 2026-09-15

### Two AI Agents Walk Into a Job Interview What if the future of hiring doesn't involve you scrolling through job boards at 2 a.m.? Instead, imagine an AI that knows your career goals inside and out—and another AI that knows exactly what a company needs. When they agree you're a match, you get an introduction. No applications, no cover letters, no ghosting. That's the bold vision behind Jack & Jill, a London-based startup that just raised €34.68 million ($40 million) in Series A funding. The round was led by Air Street Capital, with new investors Madrona and Antler joining. Existing backers like Creandum, Ada Ventures, Entrepreneurs First, and others also piled in. It's a strong signal that the hiring industry is ripe for disruption. ### Meet Jack and Jill: Your New Career Advocates Founded in March 2025 by Matt Wilson and Saaras Mehan, Jack & Jill operates two distinct AI agents. Jack works for job seekers, having voice conversations that feel more like career coaching than a typical chatbot. People have already logged 12,000 hours talking to Jack—one user called 144 times. Through these chats, Jack uncovers things a resume never shows: a toxic manager, a desired salary, or a dream role that's a slight pivot. Jill, on the other side, represents employers. She reads job descriptions, researches the company, and asks questions to define what success looks like. Then she sources candidates directly from Jack's network—not from a pile of applications. When both agents agree, they make the introduction. No application required. > "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." — Saaras Mehan, co-founder and CTO of Jack & Jill ### The Team Behind the Bots Before Jack & Jill, Wilson co-founded Omnipresent, an employer-of-record company acquired by Deel in 2025. Mehan co-founded Kular (YC W22) and is a former England chess international. The company employs 25 people across London and San Francisco—15 of whom are former founders. That's a lot of startup scar tissue in one room. ### Traction That Speaks Volumes The Series A brings total funding to €52.9 million ($60 million), following an €18.3 million ($20 million) seed round in October 2025. That seed was led by Creandum and backed by over 75 angels, including 2016 Formula One World Champion Nico Rosberg and individuals from Lovable, Anthropic, and ElevenLabs. Since the seed round, Jack & Jill's network has grown tenfold to 350,000 professionals. Jill has worked with 5,000 businesses, including Ramp, Attio, Multiverse, and Corgi. Together, the agents have arranged 25,000 interviews and are now facilitating 5,000 more each month. Interestingly, the startup is seeing faster traction in the US than in London. Over the same post-launch period, they've completed nearly four times as many interviews across San Francisco and New York. Revenue has grown 40-fold since the seed round. The new capital will primarily fund US expansion. ### What This Means for the Future of Work Wilson predicts that by 2030, a billion people will have an AI agent searching every opportunity on their behalf. Every company will have one helping it hire. Connecting those agents could make the job market run like clockwork—uncovering opportunities on both sides that would otherwise be missed. Is this the end of the resume black hole? Not entirely. But it's a compelling alternative to the broken application process. And with $40 million in fresh funding, Jack & Jill is betting big that agents—not applications—will broker the next generation of hires.