Jack & Jill

Jack & Jill is a recruiting product built around two conversational AI agents that sit on opposite sides of a hire. Jack is an AI agent that works for candidates, learning what they want and monitoring openings on their behalf, while Jill works for companies, building a detailed picture of who they need and surfacing matches from Jack's network. When both agents see a mutual fit, the product produces a direct introduction between the candidate and the decision maker rather than routing through job boards or cold outreach. According to the launch video, the network already covers roughly half a million people across San Francisco, New York, and London, which is the geography this raise is meant to deepen. The launch marks a $40M Series A led by Air Street Capital, with participation from Madrona and Creandum. It comes only months after a $20M seed led by Creandum in October 2025, backed by Dig Ventures, Entrepreneur First, Ada Ventures, Firedrop, Repeat.vc, Episode1, Playfair and angels from Lovable, Anthropic and ElevenLabs . For operators tracking the AI recruiting space, the notable pattern is the pace of follow-on capital and the bet that agent-to-agent matching can compete with both agency recruiters and job boards on the same axis. The company is based in London and was founded in early 2025 by Matthew Wilson, who scaled HR technology firm Omnipresent from 0 to a $600m valuation in three years, and Saaras Mehan, YC-backed founder of Kular.ai and former England Chess Team member . Wilson, who posted the launch, frames the thesis around how people spend their working hours, arguing that recruiters offer nuance without scale, job boards offer scale without nuance, and AI-generated applications have made the noise worse. Jack & Jill's pitch to founders and hiring managers is a way to get warm, briefed introductions at internet scale, with recent product updates letting hiring teams review candidates and request intros from inside Slack.