Jack & Jill Raises $40 Million To Put AI Agents on Both Sides of Hiring

Jack & Jill has raised $40M in Series A led by Air Street Capital to scale AI hiring agents.

The startup runs “Jack” for job seekers and “Jill” for employers. They only match when both agree.

350,000 candidates and 5,000 companies already use it. 5,000 interviews booked per month.

Hiring today is more difficult than it has ever been. If you post a job on LinkedIn, you get 1,000 applications in 6 hours. Most are spam. Many are from AI bots applying everywhere.

On the other hand, candidates send hundreds of applications and hear nothing back. Recruiters can’t tell who’s serious. Candidates can’t tell if the job is real. To solve this, Jack and Jill raises $40 million to put AI agents on both sides of hiring.

London-based Jack & Jill just raised €34.68 million, about $40 million, in Series A funding. The round was led by Air Street Capital. New investors Madrona and Antler joined. Old backers like Creandum and Ada Ventures also put in more.

This brings total funding to $60 million in less than a year. They raised a $20M seed 6 months ago. The new capital inflow will go to US expansion. They’ve already launched in San Francisco and New York.

Jack & Jill was founded in March 2025 by Matt Wilson and Saaras Mehan. Wilson was frustrated with how inefficient and biased recruitment was.

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Instead of one platform, Jack & Jill puts an AI agent on each side of the hiring table.

Meet Jack. He works for you, the job seeker. Jack talks to you with voice calls. People have logged 12,000 hours talking to him. One person called 144 times.

Jack asks about what you really want. Not just what’s on your resume. He’ll ask about a bad manager you had or the salary you need. He scans millions of open roles every day. Think of him as a career coach that never sleeps.

Meet Jill. She works for the company. Jill reads the job description, but she doesn’t stop there. She researches the company and asks what “success in the role” actually looks like. Then she sources candidates directly from Jack’s network. Not from an open applicant pool.

When Jack thinks you’re a good fit, and Jill thinks the company is a good fit, only then do they introduce you. It’s like having two negotiators who only make the intro when both sides would take the call.

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Jack’s network grew to 350,000 candidates. Jill works with 5,000 businesses, including Ramp, Attio, and Multiverse. The agents have already arranged 25,000 interviews. Now they’re doing 5,000 per month. 7800

Revenue is up 40x since the seed round. Jack is free for job seekers. The company makes money by charging employers a 10% commission on successful hires.

The $40M will fund US growth. The founders have a big vision. By 2030, Wilson says a billion people will have an AI agent searching jobs for them. Every company will have one helping them hire. Connecting those agents is what makes the market work.

It uncovers opportunities that would otherwise be missed. They’re also building out the product. Jack talks to people on voice, email, and WhatsApp. Jill digs deeper into what success looks like in a role.

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