Startup Jack & Jill Secures $20 Million for AI Job Matching

A London-based startup, Jack & Jill, has successfully raised $20 million to enhance its innovative AI recruitment technology. The funding will support the growth of its AI agents, designed to autonomously match job seekers with potential employers. The startup has reportedly gained traction, with over 49,000 job seekers and hundreds of companies utilizing its services.

Jack & Jill has created two conversational AI agents, named Jack and Jill, tailored for both job seekers and companies. The Jack agent assists candidates by gathering data from their LinkedIn profiles, CVs, and through a brief introductory conversation. It then scours the internet for suitable job opportunities, offers coaching, and conducts mock interviews to prepare candidates for the hiring process.

On the other side, Jill collaborates with companies to understand their recruitment needs better. It analyzes job descriptions and engages in discussions with the in-house talent teams. Jill can review applications, source candidates from platforms like LinkedIn, and conduct initial interviews, streamlining the hiring process.

Matthew Wilson, cofounder and CEO of Jack & Jill, emphasized the dual capabilities of the AI agents, stating, “AI enables us to combine the nuanced understanding that a human can have, with the scale that you can get from technology.” Wilson and cofounder Saaras Mehan launched the startup six months ago, driven by their frustrations with inefficiencies in traditional recruitment methods.

The service is available for free to job seekers, while Jack & Jill charges companies 10% of the base salary for successfully placed hires. Notable clients include Airtable, Airwallex, and TrueLayer, reflecting the startup’s growing reputation in the industry.

Wilson believes that AI will significantly disrupt various roles in the job market. He noted that while AI can handle repetitive tasks, there remains a crucial need for human involvement in fostering quality conversations and strategic decision-making within recruitment.

With a team of 12 employees, Jack & Jill integrates AI across various functions, such as coding, generating marketing videos, and analyzing user interactions to maximize efficiency.

Investment in agentic AI startups is on the rise, with $2.8 billion allocated globally in the first half of 2025, according to Dealroom data. This surge reflects a broader trend where startups are leveraging AI technology across diverse sectors, including customer support and cybersecurity.

Jack & Jill’s seed funding round was led by Creandum, with support from Dig Ventures, Entrepreneur First, Ada Ventures, Firedrop, Repeat.vc, Episode1, and Playfair. Additionally, over 50 angel investors from companies such as Lovable, Anthropic, and ElevenLabs contributed to the financing.

Moving forward, Jack & Jill plans to utilize the new funding to expand its presence in Europe and the San Francisco area, aiming to increase its impact on the recruitment landscape. The pitch deck that secured this substantial investment has been made available to the public, with sensitive content redacted for confidentiality.