With endless job board scrolling and the confusing surge of AI-generated fake applicants flooding the market, searching for a job online has quickly become one of the most perplexing digital experiences. Job postings are repeatedly shared across multiple sites, while applications often go unanswered, resulting in a torrent of activity that feels like spam for both employers and job seekers.
“If you advertise a position on LinkedIn, you could see 1,000 applications roll in within just six hours,” explains Matt Wilson, an entrepreneur based in London. “Many companies don’t even bother to review all those applications, because the useful ones are buried in so much noise.”
To address this, Wilson has launched Jack & Jill, a new platform that leverages conversational AI to completely overhaul the hiring process. The company just revealed a $20 million seed round led by EU investor Creandum, though it hasn’t exactly been operating in secrecy. The service is already available in London, where it has attracted close to 50,000 users. Wilson plans to use the new funding to expand into the US and further develop Jack & Jill’s capabilities.
“Since LinkedIn and Indeed emerged two decades ago, the way people look for jobs hasn’t fundamentally changed,” Wilson notes. He believes that, with AI chatbots transforming workplaces globally, now is the perfect moment to disrupt the status quo.
As its name suggests, Jack & Jill operates as a dual-sided platform. The “Jack” component is designed for job seekers, offering a 20-minute AI-driven interview to build a profile before presenting a curated selection of job opportunities from online sources. Users can then use Jack for practice interviews or more comprehensive career coaching. On the employer side, “Jill” helps companies define role requirements and highlights candidates who best fit those needs. Like LinkedIn, the platform encourages both job hunters and recruiters to stay active on their respective apps, allowing the system to engage users as opportunities arise. The platform earns a typical commission for every successful placement, and as it expands, Wilson envisions Jack & Jill becoming essential for both employers and applicants.
While this may sound like a conventional recruitment tool with some AI features, Wilson argues that conversational chatbots offer more value than basic matching algorithms. By centering the process around chatbot-led interviews, he believes he’s created a scalable alternative to the endless cycle of job postings and resumes, potentially redefining the fundamentals of modern hiring.
AI-powered initial interviews are already a common practice in many regions—especially in China, where numerous global companies use them to fill local positions. Although being interviewed by an AI recruiter might feel impersonal, Wilson hopes Jack & Jill’s method will ultimately lead to smarter, more effective job placements.
“I believe the way people are matched with employers, and vice versa, is highly inefficient,” Wilson says. “There are billions who could be in roles better suited to them. That’s a challenge worth tackling.”
A previous version of this article included an incorrect number in the headline. TechCrunch apologizes for the mistake.
