Matthew Wilson
Co-Founder & CEO | Jack & Jill
18 Feb 2026OpenClaw Joins OpenAI, Legora Eyes $6B, Netherlands Tax Unrealised Gains
Jack & Jill Founder Matthew: AI Agents for Hiring
After a Polymarket sponsor read, founder Matthew introduces Jack & Jill, an 11-month-old AI recruitment company where Jack coaches candidates and Jill works with hiring companies, following a $20M seed from Creandum and a recent launch in San Francisco. He explains Jack's evolution into a full career coach and what data from roughly 110,000 users shows: a diverging labor market with AI-native engineers in extreme demand while entry-level and early-career workers struggle. He also discusses AI's coming disruption of white-collar work, the value of live rather than backward-looking market data, Jack 2.0 and plans for the year, and why they kept the HQ in London instead of San Francisco.
18 Oct 2025Jack and Jill raise $20m, Oura hits $11bn, UK IPO Market, IPO push for Nscale, Waymo announce London
Jack & Jill founders on their $20M seed round
Jack & Jill founders Matt and Saras join fresh off announcing a $20 million seed round led by Creandum. They explain the two-sided product — Jack, a free AI career agent that interviews candidates, and Jill, an AI internal recruiter that knows companies deeply — charging a ~10% success fee on hires, roughly half a traditional agency's rate, arguing AI plus recruiter-grade nuance can outperform agencies. They discuss expanding from London tech startups to San Francisco, deploying the round across two products and multiple markets, and hiring former Fyxer CMO Frankie for consumer marketing. After they leave, the hosts note that building B2B and B2C at once fails 99 times out of 100, but are bullish on this team.