Jack & Jill Raises $40M to Revolutionize Hiring with AI Agents
Jack & Jill has raised $40M in a Series A round led by Air Street Capital, bringing their total funding to $60M less than a year after securing $20M in seed funding. New investors include Madrona and Antler, alongside returning investors Creendum, Ada Ventures, Entrepreneurs First, Expedite Capital, and Repeat.vc.
The startup has developed two AI agents: Jack and Jill. Jack acts on behalf of job seekers, learning their preferences through voice calls, emails, and WhatsApp. Jill, on the other hand, represents employers, analyzing job descriptions and interrogating the criteria for success in the role. When both agents agree that a match is beneficial, the candidate is directly introduced to the hiring manager, eliminating the need to fill out applications.
Nathan Benaich, General Partner at Air Street Capital, highlights the unique approach:
“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.”
Matt Wilson, co-founder and CEO of Jack & Jill, simplifies the concept:
“Every company has someone paid to represent its interests in the job market. People have never had the same for their careers.”
The platform boasts impressive traction:
- Jack’s network has grown tenfold since the seed round, reaching 350,000 people.
- Jill has collaborated with 5,000 businesses, including Ramp, Attio, Multiverse, Corgi, Tavus, Faculty, and Fyxer.
- Together, the agents have arranged 25,000 interviews, conducting approximately 5,000 interviews per month.
While the company doesn’t disclose the number of hires resulting from these interviews, they highlight the depth of conversations users have with Jack, including one user who engaged in 144 calls and spent over 44 hours chatting, demonstrating a high level of user commitment.
The announcement avoids discussing regulatory implications, but it’s worth noting that recruitment and candidate evaluation fall under the high-risk category as per the EU AI Act. While the obligations were deferred until December 2027, the transparency duty has been in effect since August 2026, requiring clear disclosure when interacting with AI systems, including automated phone systems. GDPR Article 22, covering automated decision-making, also applies.