Jack & Jill AI
Category: AI in HR & Talent
A conversational AI platform that uses two distinct AI agents, Jack and Jill, to connect job seekers with employers in a personalized and efficient manner Jack & Jill AI was founded in 2025. The company is led by Matthew Wilson. Based in London, United Kingdom. Team size: 12. Total funding raised: $20 million. Latest round: Seed. Key investors include ["Creandum (lead)","Ada Ventures","Entrepreneur First","DIG Ventures","Firedrop","Repeat.vc","Episode1","Playfair","75+ angel investors including Nico Rosberg"].
- Founded
- 2025
- Headquarters
- London, United Kingdom
- Team size
- 12
- Total funding
- $20 million
Value proposition
For job seekers: personalized career assistant that understands skills and ambitions beyond resumes. For employers: more efficient, human-like recruitment process from sourcing to initial interviews, improving match quality at half the cost of agency recruiters
Products and solutions
["Jack: AI career agent that conducts conversational interviews, provides career clarity coaching, salary benchmarking, mock interviews, salary negotiation coaching, and direct introductions to hiring managers","Jill: AI recruiting agent that works with employers to define hiring needs, calibrates candidate briefs, sources from Jack's network, and conducts initial screenings","End-to-end recruitment automation with 10% fee structure (vs 20-30% for traditional recruiters), full refund guarantee if hire leaves within 3 months"]
Unique value
Dual-agent conversational AI model (Jack for candidates, Jill for employers) that creates human-centric experience and captures nuanced candidate aspirations and employer requirements. Claims to combine nuanced human understanding with technology scale
Target customer
Job seekers seeking a personalized job search experience; employers (particularly in tech and startups) seeking to streamline hiring and find better-matched candidates
Industries served
["Technology","Startups","High-growth companies","Recruitment and HR"]
Technology advantage
Proprietary conversational AI that goes beyond keyword matching to facilitate deeper dialogue, enabling more accurate matches. Charges 10% of first-year salary vs 20-30% for traditional recruiters. Offers money-back guarantee if hire leaves within 3 months
How they differentiate
Uses conversational AI agents to provide personalized and automated job matching service, replacing traditional listings and resume filtering with interactive, recruiter-like dialogue. Claims 50% cost savings vs traditional recruiters
Main competitors
["LinkedIn","Indeed","Traditional recruitment agencies","Other AI recruitment startups"]
Key partnerships
["Creandum (lead investor)","Ada Ventures","Entrepreneur First","DIG Ventures","Firedrop","Repeat.vc","Episode1","Playfair","75+ angel investors including Nico Rosberg and executives from Anthropic, Lovable, ElevenLabs"]
Notable customers
["Airtable","Airwallex","TrueLayer","Maze","Encord","Architect"]
Major milestones
["Secured $20M seed funding within 6 months of founding","Reached 180,000+ candidate engagements","Hundreds of employer integrations in London","Preparing US expansion to San Francisco Bay Area"]
Growth metrics
180,000+ professionals have engaged with Jack; Jill embedded with hundreds of high-growth London companies; Jack scans 14 million jobs every day
Market positioning
Positioned as next-generation talent acquisition platform offering more efficient, less biased, and deeply personalized alternative to traditional job search methods. Free for job seekers, commission-based for companies
Geographic focus
Currently live in London with planned expansion to US market (San Francisco Bay Area)
Patents and IP
No patents or specific IP information publicly available as of December 2025
About Matthew Wilson
Founder of HR tech scaleup Omnipresent; scaled Omnipresent from startup to $600M valuation in three years
Official website: https://jackandjill.ai