$40m · Other round · HRtech · London, UK
Jack & Jill has raised $40m in Series A funding led by Air Street Capital, with participation from Creandum and Madrona, according to the company’s 15 September announcement. The London-headquartered startup operates two AI agents: Jack represents job candidates and Jill works for employers.
The financing follows a $20m seed round. Jack & Jill did not publish a valuation or detailed spending plan, but said it is hiring across London, San Francisco and New York as it develops its two-sided hiring network.
Matching both sides changes the funnel
Traditional recruitment software generally helps one side search a database or process applications. Jack & Jill is designed around a different event: an introduction happens only when the candidate-side agent and employer-side agent both judge the match worth pursuing. Jack gathers information about a person’s goals, compensation and preferences through voice conversations; Jill learns the requirements behind a role and the characteristics of successful hires.
That mutual threshold is the commercial mechanism. Employers receive fewer speculative applications, while candidates can surface preferences that do not appear in a CV or public profile. The company says 380,000 people across London, San Francisco and New York have used Jack, and more than 5,000 companies use Jill, including Ramp, Multiverse, Maze and Attio.
Madrona’s investment note says the platform has arranged 25,000 interviews and is adding about 5,000 a month. Those are company and investor claims rather than disclosed hire outcomes, but they provide an early measure of whether conversations are becoming employer introductions.
Candidate trust is the marketplace asset
Recruiting products usually monetise the employer because companies hold the hiring budget. Jack & Jill is betting that a useful candidate-side agent can create the supply and preference data that attracts employers. If Jack becomes a service people use throughout their careers, the network can include professionals who are open to the right move without actively applying for jobs.
That model depends on trust. Candidates must be comfortable sharing sensitive career and salary information, and employers must believe the agent is filtering for genuine interest rather than generating more automated outreach. The company’s decision to expand city by city—from London to San Francisco and then New York—gives it a way to build density on both sides before widening the network. Madrona says the US business is already outpacing the home market, but the next test is whether interview growth translates into durable placements and repeat employer demand.
