

Jack & Jill, a hiring platform powered by conversational generative artificial intelligence, said today it has raised $20 million in seed funding led by Creandum.
Every year, millions of job seekers go online to find employment and 68% of companies said they used online platforms for “all” or “most” of their hiring, according to a report from iHire. But despite this digital shift, the experience has deteriorated for both employers and candidates.
“Hiring is broken for candidates and companies. Misaligned incentives, spammy outreach and crowded inboxes,” Chief Executive Matthew Wilson said in the announcement.
According to Wilson, AI has made the problem worse. It has enabled job seekers to generate generic cover letters and flood job boards with automated applications, while recruiters increasingly rely on keyword-based filters that screen out qualified candidates with little context.
“We’re not adding a layer on top of that messy system,” said Wilson. “We’re rethinking it from first-principles, equipping everybody with an agent that works for them.”
Given the name of the company, it’s easy to understand that the platform is a two-part system.
Jack is a conversational AI chatbot that does intake interviews with job seekers. It gets to know them, understands their skills and experience, and works through what they really want out of their career. It does this with a 20-minute profile interview that gives users a real chance to describe their experience and role in the workplace, as well as their ambitions.
The platform can also be used for mock interviews or more involved “coaching” to provide users with the tools needed to land their preferred job.
Jill, on the other hand, works with employers by building a profile of specific roles and job opportunities, then uses information from the solution to find applicants that fit those requirements and company needs.
Wilson said in just six months, already 49,000 candidates have spoken with Jack, and Jill has managed the initial recruitment process for hundreds of high-growth companies in London.
“Talking to Jill was a surprisingly valuable experience — she had way more context than we expected, and we’re already speaking to some excellent candidates as a result,” said Eric Landau, co-founder and CEO of data annotation platform Encord.
Jack is currently free for job seekers. The company earns revenue by charging employers a 10% commission on successful hires that Jill helps facilitate.
This year has seen a wave of AI-driven hiring platforms gaining traction. Freelancer marketplace Upwork Inc. upgraded its AI capabilities with an instant-interview chatbot feature, while recruiting startup Mercor Inc. raised $100 million. Even Google LLC has entered the space with Career Dreamer, an experimental AI-powered career assistant designed to help students, recent graduates and other job seekers explore opportunities in the workforce.
Although Wilson noted that AI is breaking the job marketplace, it’s still early in deciding if AI will repair it. With this $20 million raise, Jack & Jill has a chance to help change the current experience of looking at postings online and then trying to get noticed amid hundreds or more potential candidates bustling for the same role.
Wilson said the company intends to set its sights on broader job markets with an international expansion. The company also has plans for major updates to the platform coming in the next few months.
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