As co-founder and CEO of Jack & Jill, Matthew Wilson has built two AI agents to work on opposite sides of the hiring market. Jack works for candidates, learning what they actually want from their careers and searching millions of opportunities on their behalf. Jill works for companies, turning a hiring brief into a search for people who could genuinely fit the role. When both sides agree, they make the introduction directly, without an application.
Jack & Jill says more than 380,000 professionals are now using Jack, while more than 2,000 companies use Jill. Jack scans around 15 million jobs each day, and the company says its agents have reviewed more than 100 million job matches.
That scale matters because Wilson is officially challenging the basic architecture of the hiring market.
His argument is that conventional hiring gives employers representation but leaves candidates largely on their own. Recruiters have databases, sourcing tools and increasingly powerful AI. Candidates only have job boards, CVs and application forms. In Wilson’s view, the result is a market flooded with automated applications and automated outreach, but short on genuine understanding. Jack & Jill’s answer is to give both sides an agent that knows what they want and can negotiate the space between them.
It is a particularly relevant proposition as AI changes the labour market itself. For graduates and early-career workers, traditional entry-level routes are already becoming more difficult, while employers face unprecedented volumes of AI-assisted applications. Recent reporting has highlighted both trends, making the question of how people and companies find one another increasingly consequential.
Before Jack & Jill, Matthew Wilson co-founded Omnipresent and spent years dealing with the mechanics of building teams across borders. That experience led him to the realisation that the hardest part of building a company is often not finding people who can do a job, but understanding who should do it in the first place.
Jack & Jill is his attempt to rebuild that process around context rather than keywords. Wilson’s ambition is to create a labour market in which people no longer have to search for every opportunity themselves, and companies no longer have to sift through everyone who applies.
