Jack & Jill Raises $40 Mn Series A to Transform Hiring With AI Agents

Jack & Jill uses AI agents to support both employers and job candidates during the hiring process, aiming to make recruitment easier and more efficient.

The funding round was led by Air Street Capital, with new investors Madrona and Antler joining the round. Existing investors, including Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc, also participated, along with Dig Ventures, Firedrop, Episode 1 and Playfair.

“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,” said Mehan, co-founder and CTO of Jack & Jill.

“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,” said Nathan Benaich, General Partner at Air Street Capital.

Wilson, co-founder and CEO of Jack & Jill, said, “By 2030, a billion people will have an AI agent searching every opportunity on their behalf and deciding which ones deserve their attention. Every company will have one helping it hire. Connecting those agents will make the job market run like clockwork and uncover opportunities on both sides that would otherwise be missed.”

Jack & Jill was founded in March 2025 by Matt Wilson and Saaras Mehan. The London-based startup has built two AI agents that support both sides of the hiring process.

One of these agents, Jack, works with job seekers. It uses voice conversations to help people with their careers, making the experience more like a career coaching session than a typical job-search chatbot.

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