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 — conversational intake, job search across 15M roles/day, career coaching, salary benchmarking, mock interviews, negotiation coaching, direct intros to hiring managers, Jill: AI recruiting agent — builds hiring briefs, sources from Jack's network, shortlists in minutes, Slack/Ashby integrations, Jill free to start with pricing that scales with hiring (positioned at ~half traditional agency cost); Jack free for candidates
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
Fyxer, Caura, Maze, Architect, Kyra, Omnea, Marloo, Stitch Health, Strala, Round Treasury
Major milestones
Secured $20M seed funding within 6 months of founding (Oct 2025), Scaled to 371,000+ professionals on Jack and 2,000+ companies on Jill, Expanded hiring footprint to San Francisco alongside London, Launched Slack/Ashby integrations and Friends of Jack & Jill partner program (2026)
Growth metrics
371,000+ professionals working with Jack; 2,000+ companies on Jill; Jack scans 15 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
Live in London with active US presence (San Francisco hiring; Jill serving London, San Francisco and New York startups)
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
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Official website: https://jackandjill.ai
