The job-hunting experience has become increasingly chaotic, from endless scrolling through job boards to AI-generated fake applicants flooding postings. To tackle this growing dysfunction, London entrepreneur Matt Wilson has launched Jack & Jill, a conversational AI platform aiming to reinvent how people find and fill jobs.
The company announced $20 million in seed funding led by Creandum, with plans to use the investment to expand into the U.S. market. Already live in London, Jack & Jill has attracted nearly 50,000 users in its early phase.
Wilson argues that little has changed in recruitment since the rise of LinkedIn and Indeed two decades ago. His vision: use AI-driven chatbots to streamline matching between applicants and employers, replacing the noisy flood of resumes with meaningful, data-rich conversations.
The platform is split into two parts, “Jack” for job seekers and “Jill” for employers. Jack uses AI interviews to assess candidates and recommend roles, while Jill helps companies define roles and identify the best matches. The service earns revenue through standard hiring commissions and plans to become a go-to ecosystem for both workers and recruiters.
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By relying on conversational AI, Wilson believes Jack & Jill can offer a scalable alternative to traditional listings and resumes. “There are billions of people out there that could be in better jobs for them,” Wilson said. “And that’s a mission worth working on.”
