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

Between infinitely scrolling job boards and the puzzling rise of fake applicants using AI to apply en masse, job-searching has quickly become one of the most bewildering experiences the internet has to offer. Listings are posted and re-posted across different platforms as applications go unanswered, creating a spam-like flood of activity on both sides.

“If you put a job on LinkedIn, you might get 1,000 people applying for that job within the first six hours,” says Matt Wilson, a London-based serial entrepreneur. “Some companies don’t even review the applicants that apply for those jobs, because the signal to noise ratio is very, very low.”

Wilson’s new solution is Jack & Jill, a new platform that uses conversational AI to reinvent the recruitment process from the ground up. The company announced $20 million in seed funding today, led by EU investor Creandum, but it’s hardly been in stealth. Service is already live in London, where the outfit has garnered nearly 50,000 users — and Wilson wants to use the influx of cash to fuel a US expansion and take Jack & Jill to a new level.

“There hasn’t been a major change in how people find jobs since LinkedIn and Indeed came on the scene 20 years ago,” says Wilson. His bet is that, with AI chatbots changing workplaces across the world, now might be the 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, giving users a 20-minute, AI-powered profile interview before providing them with a select list of roles pulled from online databases. From there, Jack can be used for mock interviews or more involved professional coaching. “Jill” works with employers, building a profile of a particular role and elevating candidates that match its requirements. Like LinkedIn, part of the goal is for both workers and hiring managers to keep an active presence on their respective apps, letting the app pull players off the sidelines as needed. The service takes a standard commission from any successful hire, and as the scope of the platform grows, Wilson hopes to make Jack & Jill indispensable for both sides.

That might sound like a standard recruiting system with a little AI sprinkled on top, but Wilson thinks conversational chatbots are more important than a simple matching algorithm. By building the process around chatbot interviews, he believes he’s found a scalable alternative to the endless shuffle of listings and resumes, potentially reinventing the basic elements of the contemporary hiring process.

Using AI systems to conduct first-round interviews is increasingly common in many parts of the world — particularly in China, where many multinational corporations have used the practice for hiring local roles. But while a surprise interview with an AI hiring manager might seem alienating, Wilson hopes that Jack & Jill’s approach will result in more intelligence applied to job placement overall.

“I think the way that we are mapped to the companies we work for, and vice versa, is just extremely inefficient,” Wilson says. “There are billions of people out there that could be in better jobs for them. And that’s a mission worth working on.”