Jack & Jill, a London-based recruitment platform, has secured $40M in Series A funding led by Air Street Capital, pushing its total capital raised to $60M within less than a year of closing a $20M seed round. Madrona and Antler joined as new backers, while Creandum, Ada Ventures, Entrepreneurs First, Expedite Capital, and Repeat.vc all participated again.
The company operates a two-sided AI agent system designed to reshape how candidates and employers connect. Jack represents job seekers, engaging them through voice calls, email, and WhatsApp to understand their career priorities and constraints. Jill represents employers, analyzing job descriptions and probing what genuine success in a role entails. When both agents determine a match warrants introduction, the candidate meets the hiring manager directly, bypassing traditional application processes.
According to the company, 350,000 people have interacted with Jack, while 5,000 businesses have used Jill. Together, the agents have orchestrated 25,000 interviews and are now facilitating 5,000 monthly. However, the company has not disclosed how many of these interviews resulted in actual job placements.
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 at Air Street Capital
Co-founder and chief executive Matt Wilson frames the candidate-side value proposition more directly:
Every company has someone paid to represent its interests in the job market. People have never had the same for their careers.
Matt Wilson, co-founder and chief executive
Jack's user base has expanded tenfold since the seed round. Jill's client roster includes Ramp, Attio, Multiverse, Corgi, Tavus, Faculty, and Fyxer. The platform reports a 40-fold revenue increase since the seed, though the company has not disclosed the baseline figure.
A notable data point underscores user engagement: participants have logged 12,000 hours in recent months conversing with Jack. One user has called 144 times, accumulating 44 hours of conversation about career decisions. Through these interactions, users share sensitive information—difficult managers they wish to leave, salary expectations they hesitate to voice, and problems they would accept lower compensation to solve. Jack's developers argue this depth of personal career data exists nowhere else and cannot be extracted through conventional scraping.
The announcement does not address regulatory considerations, which loom large for the sector. Under Annex III of the EU AI Act, recruitment and candidate evaluation fall into the high-risk category. While full compliance obligations were deferred to 2 December 2027 by the Digital Omnibus, Article 50's transparency requirement took effect on 2 August 2026, mandating clear disclosure when users interact with AI systems, including automated phone systems. GDPR Article 22, which governs automated decision-making, applies independently. A voice agent that determines which candidates advance to hiring managers operates within this regulatory scope.
Jack & Jill is not alone in this market interpretation. Ethos raised $22.75M in May, backed by a16z, for voice-agent interviewing that connects vetted specialists to opportunities. Ethos co-founder and chief technology officer Saaras Mehan identifies the same underlying dynamic: AI-powered candidate screening has inflated qualification signals while employer-side evaluation has stalled. Traditional corporate hiring cycles have lengthened from four months to twelve to eighteen months, and some employers are quietly rehiring workers they previously dismissed for AI, often at reduced salaries. Mehan incorporates this displacement narrative into the company's positioning.
Wilson previously founded Omnipresent, an employer-of-record firm that Deel acquired last year. Mehan co-founded Kular and represented England in chess competition.
Interview volumes in the United States are running nearly four times higher than London's rate during the equivalent post-launch period—a pattern familiar to British startups seeking international scale, though not an encouraging one.
Source: The Next Web
