Jack & Jill Raises $40M Series A to Make Warm Introductions at the Scale of the Internet

Jack & Jill, an AI agent for your career, led by Matthew Wilson and Saaras Mehan, has raised a $40M Series A, led by Air Street Capital with participation from Creandum and Madrona, to move faster toward a job market where every person and company has an agent in their corner.

Jack is an AI agent for candidates, while Jill is an AI agent for employers. When the two identify a potential match, they connect the candidate and company directly, removing the traditional application process.

The approach aims to address a fundamental problem in recruitment: balancing scale with understanding. Job boards provide reach but leave candidates to navigate countless opportunities, while recruiters offer context and judgment but can only represent a limited number of clients.

As a result, candidates often see only a small fraction of relevant opportunities, while companies struggle to identify the right people. AI agents operating on both sides of the market are designed to connect candidates and employers more efficiently, based on skills, preferences, context, and fit.

“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 network brokered by agents that understand what both sides want.”

— Saaras Mehan, CTO.

For the first time, AI agents can combine the scale of the internet with the context of a personal introduction.

Around 380,000 people across San Francisco, New York, and London are using Jack, a voice agent that learns what they want from their careers. More than 5,000 companies are hiring through Jill, including Corgi, Ramp, Multiverse, Maze, and Attio.

Jack and Jill facilitate introductions between candidates and companies, aiming to make the hiring process more direct and personalized while expanding access to opportunities.

“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.”

— Nathan Benaich, General Partner, Air Street Capital.

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