Finding a job has never felt more chaotic.
Between endless scrolling on job boards and waves of AI-generated applications flooding recruiters’ inboxes, both job seekers and employers are struggling to connect in meaningful ways.
“Post a job on LinkedIn and you might get 1,000 applications in a few hours,” says Matt Wilson, the London-based entrepreneur behind Jack & Jill, a new AI-powered recruitment platform.
“But most of those never get reviewed. The signal-to-noise ratio is terrible.”
Now, Wilson wants to fix that.
Bringing Conversation Back to Job Searching
Jack & Jill uses conversational AI to make hiring more human again – and investors are taking notice.
The startup just raised $20 million in seed funding led by European venture capital firm Creandum.
The platform is already live in London, with nearly 50,000 users, and Wilson plans to use the new funding to expand into the U.S.
“I think we’ve outgrown how job matching works,” Wilson explains. “Billions of people could be in jobs better suited for them – that’s what Jack & Jill is here to fix.”
A Modern Twist on the Hiring Process
It’s been nearly two decades since LinkedIn and Indeed reshaped online recruiting.
Wilson believes the next big leap will come from AI-driven, conversational matching.
As the name suggests, Jack & Jill operates as a two-sided platform:
| Platform Side | Function |
|---|---|
| Jack | Works with job seekers, guiding them through an AI-powered 20-minute profile interview. It then curates a shortlist of relevant roles and offers mock interviews or professional coaching. |
| Jill | Partners with employers to build detailed job profiles and surface the most compatible candidates automatically. |
Both sides stay active on the platform, so the system can make connections quickly when new roles or applicants appear.
Like traditional recruiting tools, Jack & Jill takes a commission on successful hires, but Wilson says the real innovation lies in the conversational layer – not the transaction.
Why AI Chatbots Might Fix Hiring Fatigue
Using AI in recruitment isn’t entirely new. Companies worldwide – especially in China – already use automated systems for first-round interviews.
But Wilson believes conversational AI offers something different: a smarter, more scalable, and more personal alternative to the tedious resume shuffle.
Instead of sifting through a mountain of resumes or ghosting candidates, AI chatbots can:
- Conduct initial interviews in minutes.
- Ask tailored follow-up questions.
- Flag the most qualified candidates instantly.
“It’s not about replacing humans,” Wilson says. “It’s about using AI to make better matches and free people from the parts of job hunting that no one enjoys.”
The Bigger Picture
Jack & Jill’s model comes at a time when AI is reshaping how we work, from automating office tasks to rewriting the rules of creative collaboration.
As the hiring world continues to evolve, Wilson sees his platform as part of a larger mission: making sure technology helps people find work that fits, not just work that pays.
“There hasn’t been a real breakthrough in how we find jobs for nearly 20 years,” he says. “It’s time for something better.”
Key Takeaways
- Funding: $20 million seed round led by Creandum.
- Users: Nearly 50,000 in London; U.S. expansion planned.
- AI Role: Uses conversational AI to match applicants and employers.
- Goal: Reinvent job hunting by making it more efficient – and more human.
