The London-based startup is shaking up the hiring process by using chatbot interviews to match job seekers and employers more intelligently — and aims to take the concept global.
A New Take on a Broken System
Jack & Jill, a conversational AI-powered recruitment platform, has raised $20 million in seed funding led by European VC firm Creandum to expand its operations and launch in the U.S.
- The platform already has nearly 50,000 users in London.
- CEO and co-founder Matt Wilson, a seasoned entrepreneur, believes the job market is overdue for a redesign.
“There hasn’t been a major change in how people find jobs since LinkedIn and Indeed came on the scene 20 years ago,” Wilson said.
Jack & Jill: Two Sides, One Goal
The platform splits its experience into two AI-powered sides:
- “Jack” handles job seekers, using a 20-minute AI interview to generate a dynamic profile. It then recommends a curated list of jobs, not a flood of listings.
- Jack can also run mock interviews, offer career coaching, and improve candidate readiness.
- “Jill” is for employers, building intelligent role profiles and prioritizing strong candidates based on job fit.
- Employers are encouraged to maintain an active presence to enable more dynamic, ongoing recruitment.
The platform aims to replace the static shuffle of job boards with a conversation-led, context-rich hiring experience.
Beyond Matching Algorithms: Conversational Intelligence
Wilson believes that chatbots are not just a gimmick, but a fundamentally better framework for recruitment.
- Traditional job boards have become spam-like, with listings reposted and mass applications flooding inboxes.
- Recruiters often ignore thousands of applications because “the signal-to-noise ratio is very low,” Wilson noted.
With conversational AI at the center, Jack & Jill provides real-time, adaptive engagement — simulating recruiter conversations and filtering out unqualified or mismatched candidates before human involvement.
A Global Problem with a Scalable Fix
The idea isn’t entirely new — automated AI interviews are already used by corporations around the world, particularly in China. But Wilson’s approach is more user-first:
- Candidates opt-in, and the AI is designed to coach, not judge.
- The goal is to bring clarity and structure to the messy process of finding and filling jobs.
“There are billions of people who could be in better jobs for them,” Wilson said. “That’s a mission worth working on.”
Revenue Model and Expansion Plans
Jack & Jill follows a success-based commission model — similar to traditional recruiting agencies.
- As the platform scales, it aims to become indispensable to both job seekers and hiring teams.
- The $20 million will be used to:
- Fuel U.S. expansion
- Build out product features
- Hire talent across AI, engineering, and partnerships
The Challenge: Changing Default Behavior
Despite its appeal, Jack & Jill faces a steep behavioral challenge:
- Job seekers are used to LinkedIn, Indeed, and Glassdoor — systems built around static listings and resumes.
- The platform will need to prove that its AI chat-led approach is more efficient, fair, and effective for both sides of the market.
Still, with increasing frustration over traditional job search tools and growing trust in AI-enabled services, the timing could be just right.
