The Pulse
Jack & Jill raises $40M for two-sided recruiting agents
Jack & Jill has raised $40 million in Series A funding to build a recruiting service in which an AI agent represents the candidate and another represents the employer.
AI.info Team ·
“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
Jack & Jill has raised $40 million in Series A funding to build a recruiting service in which an AI agent represents the candidate and another represents the employer. Air Street Capital led the round, with Madrona joining and existing investor Creandum investing again.
The financing follows a $20 million seed round announced less than a year ago, bringing the company’s disclosed funding to $60 million. Jack & Jill says it will use the capital to move toward a job market where candidates and companies each have an agent working on their behalf.
Jack speaks for candidates; Jill recruits for companies
Jack is the candidate-side agent. People speak with it about the kind of work they want, the teams they hope to join, the conditions they would accept and the roles they would rather avoid. The company presents those conversations as a richer source of information than a résumé or LinkedIn profile, which largely records a person’s past rather than their next career move.
Jill works for employers. Companies brief the agent on an open role, and Jill develops a view of what success in that position requires before searching through Jack’s network. When both systems conclude that a match is worth pursuing, Jack & Jill introduces the candidate to the hiring manager directly, skipping the standard application process.
“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, Jack & Jill’s co-founder and chief technology officer, says in the company’s funding announcement. He argues that adding more applications and filters will not solve the problem; the company instead wants a network in which agents understand both sides of a hiring decision.
380,000 people and 5,000 companies
Jack & Jill says 380,000 people in San Francisco, New York and London have spoken with Jack about their careers. More than 5,000 companies are hiring with Jill, including Corgi, Ramp, Multiverse, Maze and Attio.
The company does not disclose how many of its introductions have resulted in hires. Its announcement describes the introductions as events with direct consequences for candidates and employers, but provides no conversion figure or revenue data.
Jack & Jill’s candidate service is built around conversation rather than a conventional job-board search. The company says Jack reads large numbers of job listings to identify a smaller set of roles that fit what a candidate has described, while Jill works from the employer’s needs and recruits from the candidate network.
Air Street’s bet on agents on both sides
For Air Street, the investment rests on the idea that hiring has lacked representation for candidates. Employers can pay recruiters to search for talent, while jobseekers generally depend on job boards, personal networks and applications that may never receive a response.
“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,” Benaich says in the announcement. The approach differs from recruiting software that automates outreach or filters résumés for only one participant in the hiring process.
Jack & Jill’s funding arrives as companies experiment with AI systems that conduct interviews, source candidates and manage parts of the hiring workflow. Its proposal goes further by giving the candidate an agent with a separate interest from the employer’s agent, then treating agreement between them as the point at which a human conversation should begin.
A marketplace built around introductions
The company’s model depends on both networks being large enough to produce useful matches. Candidates need a reason to share detailed information with Jack, while employers need confidence that Jill’s introductions are relevant enough to replace some of the early work handled by recruiters.
That makes the undisclosed hiring-conversion rate an important measure of the business. The company gives participation figures, but the funding announcement does not say how many candidates have been hired through the service.
For now, Jack & Jill’s concrete pitch is narrower: Jack learns what a person wants, Jill learns what a company needs, and the two agents arrange a meeting only when the match appears strong enough to justify one.