Jack & Jill, the London-based AI recruiting startup founded by Matthew Wilson, has raised $20 million in seed funding to transform how people and employers connect. The round was backed by top investors including Creandum, DIG Ventures, Entrepreneur First, Ada Ventures, Firedrop, Repeat.vc, Episode 1 Ventures, Playfair, and several angel investors.

With this funding, the company aims to scale its technology and expand globally - redefining what it means to have a “human” experience in the age of artificial intelligence.

AI Recruiters with a Human Touch

Jack & Jill has created two digital personas - Jack and Jill - that replicate the warmth and intuition of real recruiters. Jack guides job seekers through career goals and applications, while Jill helps employers identify, screen, and recommend talent that fits both technically and culturally.

What sets the startup apart is its focus on contextual empathy. Most AI recruitment tools prioritize efficiency and keyword matching, but Jack & Jill focuses on understanding human nuance - ambition, tone, growth trajectory, and cultural alignment. It’s less about automation for speed, and more about automation that feels alive.

The system goes beyond surface-level matching. It decodes intent, learns from every interaction, and curates opportunities that genuinely align with users’ aspirations. This approach has led to remarkable results - reducing recruitment time by up to 60% and doubling candidate engagement rates.

Scaling Emotional Intelligence in AI

Jack & Jill’s technology operates on a simple yet powerful principle: AI can’t replace human trust - but it can scale it. The startup’s proprietary models continuously learn from recruiter feedback loops and user interactions, which allows the AI to refine its tone, recommendations, and outreach.

And buried inside this progress lies something every founder should pay attention to. Jack & Jill’s true innovation isn’t just technological - it’s emotional. The company is proving that trust can be engineered. Each message, each recommendation, each interaction is intentionally designed to deliver consistency and emotional reliability.

In a world where users are trained to expect disappointment from automation, this consistency becomes the foundation of belief. The founders have understood that people don’t just want accuracy from technology - they crave dependability. This is the subtle art of engineering emotional trust at scale.

Here’s the ultra value drop - one most founders completely overlook: trust doesn’t begin with branding; it begins with pattern recognition. When a user’s fifth experience with your product feels as consistently thoughtful as their first, you’ve transcended being a tool. You’ve become a habit. Jack & Jill has achieved this by designing predictable emotional performance into every corner of its platform. Founders often chase virality, but compounding trust is the real growth engine. Technology can be copied; trust loops cannot.

The Next Chapter of Recruiting

Jack & Jill’s approach reflects a deeper understanding of how hiring truly works - not as a transaction, but as a relationship of confidence. By bridging employers and candidates through emotionally intelligent automation, the startup is reshaping recruitment into something more relational and less mechanical.

Its system runs ongoing scans across the market, learning from thousands of data points, then personalizing results based not only on skills but on ambition, personality, and communication style. Employers benefit from highly tailored shortlists, while candidates experience a sense of being genuinely seen.

That combination of intelligence and empathy is why investors are betting big. In a landscape crowded with tools that feel cold and impersonal, Jack & Jill’s warmth is its competitive advantage. The product’s tone, speed, and reliability make users feel like they’re interacting with something human - and that emotional resonance is what transforms technology into trust.

Redefining Recruitment Through Connection

This funding isn’t just capital - it’s a signal of where recruitment technology is heading. Investors like Creandum and Ada Ventures are increasingly drawn to startups that infuse emotional intelligence into automation. As the industry shifts away from brute-force optimization toward experience-driven design, Jack & Jill stands out as a blueprint for how AI can scale human-like engagement.

If the company continues executing its vision, it won’t just make hiring faster - it will make it more personal. That’s a fundamental redefinition of success in recruiting tech. Instead of focusing on volume or speed, Jack & Jill is showing the power of consistent, emotionally intelligent interactions that build loyalty and trust over time.

For founders watching this rise, the message is clear: scale isn’t just about users - it’s about reliability. When your product earns the right to be expected, you’ve crossed from startup to standard. Jack & Jill isn’t just building AI recruiters; it’s building belief, one interaction at a time.