Blog
$40M Series A to make warm introductions at the scale of the internet
The decisions we make about our careers are among the most important of our lives. And yet finding a job you love is left to chance.
Matthew Wilson
AI sourcing is broken by design. Here’s how we’re fixing it.
A response to Paul Karrmann’s article on why AI sourcing keeps failing, and how Jack & Jill is fixing the three structural problems he identified.
Matthew Wilson
Rewriting tech roles
Founders Associate, Founding GTM, MTS, Forward Deployed Engineer, GTM Engineer, Talent Engineer, Founding Operator: the new generation of startup titles and where they came from.
Arya Tandon
How to Build an AI-Native Team
Notes from the Jack & Jill x Ashby breakfast panel: how founders and talent leaders are actually getting their teams to compound on AI, not just have access to it.
Jack & Jill
How to Find a Job in 2026
A practical, step-by-step guide to navigating the 2026 job market, from working out what you actually want to landing the offer and negotiating it.
Ainhoa Arias
Press
View all 9 →- Watch video — Jack & Jill raises $40M Series A, live on TBPN (opens in new tab)
Jack & Jill raises $40M Series A, live on TBPN
Matt Wilson joins Jordi Hays and John Coogan on TBPN on the day of the raise to talk through the $40M round.
- Watch video — Matt Wilson on the $40M Series A, live on ETN (opens in new tab)
Matt Wilson on the $40M Series A, live on ETN
Matt Wilson joins the European Technology Network’s live show on the day of the raise, in a run of founder interviews from across European tech.
- Read article — Our investment in Jack & Jill: a job market that works for you (opens in new tab)
Our investment in Jack & Jill: a job market that works for you
Air Street Capital leads Jack & Jill’s $40M Series A to put an agent on both sides of the job market.
- Watch video — Will AI Kill White-Collar Jobs | Jack&Jill CEO Matt Wilson (opens in new tab)
Will AI Kill White-Collar Jobs | Jack&Jill CEO Matt Wilson
Matt Wilson joins Jimmy's Jobs of the Future to discuss how AI is flooding hiring with noise, why a CV is losing its power to signal anything, and what Jack and Jill do instead.
- Read article — Air Street Capital leads $40M Series A into Jack & Jill’s dual-agent hiring marketplace (opens in new tab)
Air Street Capital leads $40M Series A into Jack & Jill’s dual-agent hiring marketplace
Tech Funding News covers the $40 million round led by Air Street Capital, and how a pair of agents works either side of the hiring market.
- Read article — Exclusive: Agentic job platform Jack & Jill raises $40M (opens in new tab)
Exclusive: Agentic job platform Jack & Jill raises $40M
Jack & Jill, a London-based agentic job-finding platform, raised a $40 million Series A led by Air Street Capital, CEO Matt Wilson tells Axios Pro exclusively.
- Read article — Jack & Jill raises $20M to bring conversational AI to job-hunting (opens in new tab)
Jack & Jill raises $20M to bring conversational AI to job-hunting
The startup has built two AI agents, Jack for candidates and Jill for recruiters, and is expanding across London and San Francisco.
- Watch video — The future of work: AI agents for hiring and careers (opens in new tab)
The future of work: AI agents for hiring and careers
Matthew Wilson joins the EUVC podcast to discuss how AI is reshaping the global labour market and what it means for candidates and companies alike.
- Watch video — A Conversation with the AI Minister of the UK (opens in new tab)
A Conversation with the AI Minister of the UK
Jack & Jill features in a sit-down with the UK's AI Minister on how AI is transforming employment and the future of work.
