Jack & Jill, operated by Tinker Tailor Talent Ltd., a hiring platform powered by conversational generative artificial intelligence, said Tuesday it has raised $40 million in early funding to build a job market where people don’t need to apply for jobs – instead, a pair of AI agents do the work.
Air Street Capital led the Series A round, joined by new investors including Madrona, existing investors Creandum and Entrepreneurs First also participated. The funding brings the company’s total raised to $60 million, ten months after its 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 argued that the problem isn’t better filters; it’s about a better solution, and that’s going to be a marketplace brokered by the same thing that’s eating hiring right now. Jack & Jill is offering brokered AI agents that can understand what both sides want.
Professionals speak to Jack, an AI agent who takes voice calls as a career coach. In the past few months, the company says that 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, continuing 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.”
This pairing is the secret sauce of Jack & Jill, creating a two-sided conversation where job seekers and employers come together, and nobody submits a resume and an employer doesn’t need to sit down, crunch numbers and break down a role. The point is to allow the two agents to act as matchmakers based on rich contextual information rather than keywords and job roles.
According to Wilson, the hope is that it will help the job market “run like clockwork” and “uncover opportunities” that would otherwise be missed.
The company 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 over 25,000 interviews and currently handle another 5,000 each month.
