He studies broken systems for a living. Pharma supply chains. Global payroll. And now the thing almost everyone hates and almost nobody has fixed: getting hired.
Talk to Jack for twenty minutes and something odd happens. People start telling an AI the things they would never put on a resume - the sideways career move, the role they actually want, the worry about starting over. One early user finished the session and said, "I didn't want the conversation to end." Nobody has ever said that about an online application form.
That reaction is the entire thesis of Jack & Jill, the London company Matthew Wilson co-founded in early 2025. There are two AI recruiters. Jack works for the person looking for a job - interviewing them, coaching them, surfacing only the roles that fit. Jill works for the company, learning what a team actually needs and finding the right people from Jack's network. Jack and Jill, like the nursery rhyme. One goes up the hill, the other follows.
Wilson's complaint about the status quo is precise rather than vague. A single LinkedIn job can draw more than a thousand applicants in six hours. That is not a sorting problem you fix with a better filter. It is a signal problem. "The way that we are mapped to the companies we work for, and vice versa, is just extremely inefficient," he says. His rule for the team is blunt: "Don't use AI to accelerate a broken process." Rebuild the process instead.
Six months after starting, the company announced a $20 million seed round led by Creandum. By then roughly 49,000 people had already spoken with Jack in the London market. Next stop, San Francisco.
It's a low-signal, high-anxiety process for everyone. Candidates feel like a number, and companies are buried in a sea of irrelevant applications.- Matthew Wilson
Wilson grew up in Yorkshire surrounded by doctors, lawyers and accountants - the safe professions - and chose physics instead. He read Physics at Oxford, then took a Masters in Theoretical and Mathematical Physics, and went into academia to work on theoretical particle physics. It is about as far from recruitment software as a career can get.
In 2012 he walked away. The disillusionment was specific: in research, impact arrives in decades, if it arrives at all. He started building software for small businesses and found it almost suspiciously freeing that he didn't need anyone's permission to make something useful and watch it matter the same week.
The pattern that defines him showed up next. In 2017 he co-founded Veratrak, using blockchain to digitise the tangle of the pharmaceutical supply chain. Then he joined Entrepreneur First - the programme that pairs would-be founders with co-founders - and there met Guenther Eisinger. In November 2019 they started Omnipresent to handle the legal and administrative mess of hiring people anywhere in the world.
The timing was brutal and then perfect. His first investment meeting with Playfair was on 9 March 2020, the day before Italy locked down. Remote work was about to become the only kind of work. Omnipresent scaled to 150-plus people across 35-plus countries, raised a $120 million Series B, and reached a valuation of around $600 million in about three years before being acquired by Deel. Wilson didn't meet his own 120-person team in person until a retreat in Madeira in September 2021 - two years in.
Building a company that hired across 160 countries gave him a front-row view of how badly people and jobs are matched. "I spent my days in the trenches of the talent market," he says, "and it was clear to me that the system is fundamentally broken." Jack & Jill is what he decided to do about it.
A roughly 20-minute voice conversation that reads like a session with a career coach, not a stuffy interview. It captures ambition, cultural fit and the nuance of a non-linear career - the things a form throws away - then surfaces only roles that actually match, plus mock interviews and coaching.
Works with a hiring team to understand what a role genuinely needs, then finds ideal people from Jack's network. The pitch: faster and more accurate than a traditional recruiter, at up to half the cost, paid on successful hires.
Wilson's co-founder is Saaras Mehan, a Y Combinator alumnus who previously founded Kular.ai and runs the technical side of Jack & Jill as CTO. The pairing matters because the company's whole bet is that voice is a better interface for hiring than a text box, and voice agents are unforgiving to build. They have to feel like a person who is actually listening, or the magic collapses into an automated phone menu.
So the early team was assembled around that single problem. A founding engineer who had built neural voice agents before they were fashionable. A marketing lead who had taken earlier ventures to serious revenue. A deliberately small group - around a dozen people when the seed was announced - because Wilson has said before that organisational focus is everything, that every yes is an opportunity cost paid somewhere else. It is a lesson he learned the expensive way at Omnipresent, where saying yes to too much, too fast, is the default failure mode of a hypergrowth company.
The investor list reads like a vote of confidence from people who understand both AI and hiring. Creandum led. Around it sit Dig Ventures, Entrepreneur First - the programme that made Omnipresent possible - Ada Ventures, Firedrop, Repeat.vc, Episode1 and Playfair, the firm that took that nerve-wracking first meeting the day before lockdown. Then more than seventy-five angels, among them former Formula 1 World Champion Nico Rosberg and operators from Lovable, Anthropic and ElevenLabs. When the people building the frontier models and the breakthrough voice products put their own money in, they are saying the interface is ready.
Creandum, one of Europe's most established early-stage firms, anchoring a $20M seed.
Dig Ventures, Entrepreneur First, Ada Ventures, Firedrop, Repeat.vc, Episode1, Playfair.
75+ individuals, including Nico Rosberg and people from Lovable, Anthropic and ElevenLabs.
A roughly twelve-person group built around one hard thing: voice that feels human.
There is a thread running through Veratrak, Omnipresent and Jack & Jill, and it is not the technology. Blockchain, payroll and voice AI have nothing in common. The thread is the shape of the problem. Each one is a market where two sides need to find each other, where the matching is done badly, and where everyone has quietly accepted the friction as the cost of doing business. Wilson has a physicist's allergy to that kind of accepted inefficiency. If a system wastes this much energy, the system is wrong, not the people stuck inside it.
Recruitment is the purest version yet. Think about how little the mechanics have changed since LinkedIn and Indeed arrived. You write a document that flattens a non-linear life into bullet points. A keyword filter decides whether a human ever reads it. On the other side, a hiring manager drowns in a thousand applications and a recruiter charges a fee that can run into tens of thousands for the privilege of introductions. Both sides feel like they are losing. Both sides are right.
Wilson's insight is that generative AI arrives at this moment as a fork in the road. The lazy path is to bolt a chatbot onto the existing funnel and call it innovation - to use AI to send more applications faster, which only makes the signal-to-noise problem worse. The harder path is to ask what the process would look like if you designed it from scratch around how people actually talk about their careers. That is why the guiding rule is a refusal: don't use AI to accelerate a broken process.
What surprised the team most was the human response. People are more honest with Jack than with a human recruiter. They volunteer the doubts, the ambitions, the messy truth of why they want to leave - the things a candidate instinctively hides from someone who holds the keys to the job. A machine that has no agenda turns out to be a better confidant. "I didn't want the conversation to end" is not a line about software. It is a line about being heard, which is the one thing the old process never offered. If Wilson is right, the future of finding work looks less like applying and more like being known.
"Imagine a world where every person is in their perfect job, and every company has the right people. We're a long, long way from that today."
"Don't use AI to accelerate a broken process."
"Being an entrepreneur is about changing how the world works."
"Execution and results are what count."
Wilson's five-year picture flips the whole ritual: job search becomes passive. Instead of dusting off a resume when you're miserable, an AI co-pilot runs quietly in the background, learns how your skills change, and surfaces the right opportunity before you start looking. The mission, in his framing, is simple and very far off - that everyone, hiring or job hunting, gets unimaginably good support.