Jack & Jill Raises $40M Series A to Build Dual-Agent AI Hiring Marketplace

London-based AI recruiting startup Jack & Jill has raised $40 million in Series A funding to expand its dual-agent hiring marketplace and accelerate its growth in the United States.

The round was led by Air Street Capital, with Madrona and Antler joining as new investors. Existing backers including Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital and Repeat.vc also participated.

The latest financing comes just 10 months after Jack & Jill raised a $20 million seed round, bringing its total funding to $60 million.

The company says its candidate network has grown tenfold to approximately 350,000 people.

A Hiring Marketplace With Two AI Agents

Jack & Jill is taking a different approach to traditional recruitment platforms.

Instead of starting with resumes and keyword searches, the company uses two AI agents to understand both sides of the hiring process.

Jack conducts telephone interviews with candidates to understand their skills, preferences and job requirements. Jill has similar conversations with hiring managers to learn about their hiring needs.

The two agents then assess potential matches based on information collected through these conversations.

When both sides appear interested in the opportunity, Jack & Jill facilitates a direct introduction between the candidate and hiring manager, allowing the candidate to bypass the conventional application process.

The company believes voice conversations can reveal information about candidates and employers that conventional databases and resume-scraping systems may not capture.

Founders With Recruitment and Startup Experience

Jack & Jill was co-founded by Matt Wilson and Saaras Mehan.

Wilson previously co-founded Omnipresent, an employer-of-record company founded in 2019. Omnipresent reached a reported $600 million valuation before being acquired by Deel in October 2025 for approximately $15 million, according to Dealroom.

Mehan previously founded Kular, an AI sales startup that received funding from Y Combinator. He also previously competed as a chess player for England.

The founders are now pursuing a substantially larger vision for Jack & Jill, with Wilson targeting the development of a hiring agent capable of serving a billion people by 2030.

Growing Candidate and Employer Networks

Jack & Jill says its candidate network has expanded tenfold to 350,000 people since its previous funding round.

On the employer side, Jill has interacted with 5,000 companies, including Ramp, Attio and Fyxer.

The company has also expanded internationally, launching in San Francisco in January 2026 and New York in June.

Since its $20 million seed round, Jack & Jill says its revenue has increased 40 times.

The company currently has a 25-person team distributed between London and San Francisco, including 15 former founders.

Competing in an AI-Powered Recruitment Market

Jack & Jill is entering a recruitment technology market where AI is increasingly being used for candidate discovery, interviewing and matching.

Mercor has raised $100 million at a reported $2 billion valuation for AI-driven technical interviews, while Juicebox has raised $30 million for its PeopleGPT recruitment search platform. Other startups are also developing AI-powered approaches to recruitment.

Jack & Jill's model differs by attempting to replace resume-first matching with conversations between AI agents representing candidates and employers.

The company argues that simply increasing the number of applications or improving resume filters does not necessarily address the underlying trust problem between candidates and employers.

$40M to Expand in the US

The Series A funding will support Jack & Jill's continued expansion in the United States following its launches in San Francisco and New York.

The company plans to grow its marketplace, expand its network of candidates and employers, and further develop its agent-based matching technology.

With $60 million raised in total and a candidate network of 350,000 people, Jack & Jill is now scaling a recruitment model built around AI agents interviewing both sides of the hiring market before making introductions.

Its next phase will test whether this conversation-first approach can scale across thousands of companies while maintaining the quality and relevance of the matches.