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Jack & Jill Raises $20M for AI-Powered Job Search

October 16, 2025
Jack & Jill Raises $20M for AI-Powered Job Search

The Modern Job Search: A Growing Challenge

The process of finding employment has become remarkably complex, largely due to the endless stream of job boards and the increasing prevalence of AI-generated, inauthentic applications. Job postings are frequently duplicated across various platforms, while many applications remain unacknowledged, resulting in a high volume of unproductive activity for both job seekers and employers.

The Problem of Signal-to-Noise Ratio

Matt Wilson, a London-based entrepreneur, notes that a single job posting on LinkedIn can attract up to 1,000 applicants within the first six hours. Consequently, some companies forgo reviewing applications altogether, as the proportion of qualified candidates to unqualified ones is exceedingly low.

Introducing Jack & Jill: An AI-Powered Solution

Wilson’s newly developed platform, Jack & Jill, aims to fundamentally reshape the recruitment landscape through the implementation of conversational AI. The company recently secured $20 million in seed funding, spearheaded by EU investor Creandum.

Despite its recent funding, Jack & Jill is already operational in London, having amassed a user base of nearly 50,000 individuals. Wilson intends to leverage this capital to facilitate expansion into the United States and further enhance the platform’s capabilities.

A Shift in Job Search Paradigms

Wilson argues that the core methods of job searching have remained largely unchanged since the emergence of LinkedIn and Indeed two decades ago. He believes that the widespread adoption of AI chatbots in the workplace presents an opportune moment to introduce innovation to the recruitment process.

How Jack & Jill Works

The platform operates on a dual system, represented by “Jack” and “Jill.” “Jack” caters to job applicants, conducting a 20-minute AI-driven profile interview to curate a tailored list of relevant job opportunities from online databases.

Furthermore, Jack provides resources for mock interviews and comprehensive professional development. “Jill” assists employers in defining role requirements and identifying candidates who align with those needs.

Similar to LinkedIn, the platform encourages continuous engagement from both job seekers and hiring managers, proactively connecting individuals with suitable opportunities. A standard commission is charged upon successful placement, and Wilson envisions Jack & Jill becoming an essential tool for all parties involved.

Beyond Simple Matching

While the system may appear as a standard recruitment tool enhanced with AI, Wilson emphasizes the significance of conversational chatbots. He posits that structuring the process around chatbot interviews offers a scalable alternative to the conventional cycle of job listings and resume submissions, potentially redefining the fundamentals of modern hiring.

AI Interviews: A Growing Trend

The use of AI for initial interviews is becoming increasingly prevalent, particularly in regions like China, where multinational corporations frequently employ this method for local hiring. Wilson hopes that Jack & Jill’s approach will foster a more intelligent and effective job placement process, contrasting with potentially impersonal AI interviews.

A Mission to Improve Job Alignment

“The current system for connecting individuals with companies is profoundly inefficient,” Wilson states. “Countless people could be in roles better suited to their skills and aspirations, and addressing this issue is a worthwhile endeavor.”

A previous iteration of this article contained an inaccurate figure in the headline. TechCrunch apologizes for this error.

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