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Home » Jack & Jill raises $20 million to bring conversational AI to job hunting
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Jack & Jill raises $20 million to bring conversational AI to job hunting

userBy userOctober 16, 2025No Comments3 Mins Read
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Between endlessly scrolling job boards and the mysterious rise in fake applicants using AI to mass apply, job hunting has quickly become one of the most bewildering experiences the internet has to offer. If the request goes unanswered, the listing is posted and reposted on various platforms, creating a flood of spam-like activity on both sides.

“If you post a job on LinkedIn, you might have 1,000 people apply for it within the first six hours,” says Matt Wilson, a London-based serial entrepreneur. “Some companies don’t screen applicants for these jobs because the signal-to-noise ratio is so low.”

Wilson’s new solution is Jack & Jill, a new platform that uses conversational AI to fundamentally reinvent the hiring process. The company today announced $20 million in seed funding led by EU investor Creandum, but it was hardly a secret. The service has already been launched in London, where it has around 50,000 users. And Wilson hopes to use the influx of money to fuel expansion in the U.S. and take Jack & Jill to a new level.

“Not much has changed in the way people find jobs since LinkedIn and Indeed came out 20 years ago,” Wilson says. His bet is that now that AI chatbots are changing workplaces around the world, it’s time to shake things up.

As you might guess from the name, Jack & Jill is a two-part platform. The “Jack” side of the platform handles the applicant side, offering users a 20-minute AI-powered profile interview before providing them with a selection list of roles pulled from an online database. From there, Jack can be used for mock interviews and more complex professional coaching. ‘Jill’ works with employers to build profiles for specific roles and promote candidates who match their requirements. Similar to LinkedIn, one of the goals is for both employees and recruiters to maintain an active presence on their respective apps, allowing the apps to pull players off the sidelines when needed. The service receives standard commissions on successful adoptions, and as the platform expands, Wilson hopes to make Jack & Jill essential to both parties.

While this may sound like a bit of AI infused into a standard recruitment system, Wilson believes conversational chatbots are more important than simple matching algorithms. By building a process around chatbot interviews, he believes he has the potential to discover a scalable alternative to the endless shuffling of lists and resumes, reinventing the fundamental elements of the modern hiring process.

The use of AI systems to conduct initial interviews is becoming increasingly common in many parts of the world. Especially in China, many multinational companies use this practice to recruit local talent. But while a surprise interview with an AI hiring manager may feel alienating, Wilson hopes Jack & Jill’s approach will apply more intelligence to overall job placements.

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“I think the way we are mapped to the companies we work for and vice versa is very inefficient,” Wilson says. “There are billions of people out there who could use better jobs, and that’s a mission worth pursuing.”

An earlier version of this article was published with an incorrect number in the headline. TechCrunch regrets this mistake.


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