Jack & Jill raises $40M Series A for AI agents that match job seekers and employers

The round included new investor Madrona and existing investors Creandum and Entrepreneurs First, the company said. The funding brings Jack & Jill’s total raised to $60 million, ten months after a seed round led by Creandum.

“AI is displacing jobs and pushing more people into the job market,” said co-founder and Chief Technology Officer Saaras Mehan. “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.” Mehan said the problem is not better filters but a better solution, and that solution is a marketplace brokered by the same technology that is disrupting hiring. Jack & Jill offers brokered AI agents that can understand what both sides want, according to the company.

In practice, professionals speak to Jack, an AI agent who takes voice calls as a career coach. Over the past few months, the company says job seekers have spent more than 12,000 hours speaking to Jack, and one person spent more than 44 hours speaking to the agent. Many return every week to continue the same conversation. On the other side, Jill builds a detailed understanding of what each company is looking for in a hire, reading job descriptions and answering questions about what success looks like.

“Every company has someone paid to represent its interests in the job market. People have never had the same for their careers,” said co-founder and Chief Executive Matt Wilson. “By 2030, a billion people will have an AI agent searching every opportunity on their behalf and deciding which ones deserve their attention.” The pairing of Jack and Jill creates a two-sided conversation between job seekers and employers, the company said. Nobody submits a resume, and an employer does not need to sit down, crunch numbers and break down a role. The aim is for the two agents to act as matchmakers based on rich contextual information rather than keywords and job roles. Wilson said the hope is that it will help the job market “run like clockwork” and “uncover opportunities” that would otherwise be missed.

Jack & Jill said it has worked with 5,000 companies, including Tavus Inc., Fyxer AI Inc., Ramp Business Corp., Attio Ltd., Multiverse Group Ltd. and Corgi Insurance Services Inc. Together, the two AI agents have arranged more than 25,000 interviews and currently handle another 5,000 each month.