Jack & Jill AI: The AI Agent twins taking over recruitment 🧑‍💻

(7 minutes)

Hey 👋, this is the Kitsune VC Newsletter: A subset of Today in AI, where we vest a $10 million early stage fund over the next 2 years.

We make “investments” every few weeks into early stage startups we think will make it big in hopes to beat the returns of big funds like Sequoia and a16z. 💸

Today we are talking about an AI startup that can find you the perfect job or help you recruit the perfect person. 

The Problem: Hiring is noisy, and dehumanizing 🔊

Recruitment is fragmented across job boards, agencies, forms, and inboxes. 📥

Candidates struggle to tell coherent stories; hiring managers sift through low-signal CVs.

AI has made it a lot worse - mass-produced applications spike volume without increasing fit. 📄

Meanwhile, 9M+ adults in the UK alone are economically inactive, and the matching layer still fails on both sides. 📉

Candidates want guidance and momentum and employers want fewer, better matches - fast, and at lower cost than traditional agencies. 

So what if an AI actually understood candidates’ narratives and delivered pre-screened, high-signal matches on both sides?

The Solution: Jack & Jill 👫

Jack&Jill was founded by Matthew Wilson and Saaras Mehan in April 2025 (yes it’s just 6 months old) with the vision to make hiring amazing people cheaper, and faster.

The product is made up of 2 agents: “Jack” helps candidates, and “Jill” helps hiring managers.

How it works? 💭

1. Listen & Profile (Jack): Hold a 10-minute voice conversation that pulls out experience, strengths, favorite campaigns, and goals - then structure it into a candidate profile. ✨
   

2. Search & Match (Jack): Scan ~10k new jobs per hour and push “truly unmissable” roles within minutes; simulate interviews and assist with applications.
   

3. Brief & Source (Jill): Let hiring managers describe the role in natural language; Jill queries Jack’s candidate network and returns great-fit profiles fast.
   

4. Charge on Success (Jill): Employers pay 10% of first-year salary only when a hire is made; job seekers use Jack for free. 💸
   

5. Different from incumbents: Unlike job boards/ATS that optimize for clicks and forms, Jack & Jill optimize for fit via voice-native understanding + closed-loop placement.
   

Day in the life (employer): Share your brief → Jill clarifies must-haves and nice-to-haves → Shortlist of pre-screened, AI-ranked candidates → Interviews scheduled → Pay on hire.

Founders & Backstory 👀

Matthew Wilson grew up in Yorkshire in a family of doctors, lawyers, and accountants. 🧑‍⚕️

Despite his family's professional leanings, he wasn’t interested in entrepreneurship during his childhood, he loved science and maths.

That led him to the University of Oxford - he first studied Physics and then went on to complete a Master's degree in Theoretical and Mathematical Physics. He initially wanted to go full-time on academia. 📚

He scrapped that idea in 2012 after looking at the discovery of the Higgs boson at CERN. 🦠

Peter Higgs had to wait 65-70 years for his PhD thesis to "pay off," a timeline Wilson found "pretty brutal" and felt it wasn't the "most rewarding career". 😔

After leaving academia, Wilson found a new path by working with small businesses. It was "refreshing" as it showed him that he "didn't need to ask for permission to go and create something that could have an immediate impact on the world".  🌎

He also spent a bunch of time as a software engineer and product manager.

He then founded Veratrak in 2017 with Jason Lacombe, whom he met at University.

Veratrak developed blockchain-based software for pharmaceutical supply chains, by digitizing documentation. 💊

It was backed by Seedcamp and got Matthew into Forbes 30 Under 30 Europe in 2019 for Manufacturing & Industry. 🏆

Veratrak did well but Matthew later said that it "wasn't a space I was passionate about".

Matthew then joined Entrepreneur First (EF)’s program to connect with other founders and build another startup. 

This is where he met Guenther Eisinger, the co-founder for his next startup - Omnipresent. Their goal was to solve the challenges companies faced in managing remote teams, an idea many investors initially thought was "10 years too early". 

COVID then hit, and it kind of exploded. 💥

Omnipresent rapidly became one of the UK's fastest-growing startups, raising $120 million by Series B. 🚀

It helps clients, including QuotaPath, Halfbrick, and Supercede, hire global teams across over 160 countries.

Jack&Jill Early Beginnings 🐣

This is when Matthew had an insight: Recruitment felt “crap, noisy, and dehumanizing,” worsened by AI-generated application floods. 

Counterintuitively, the fix for “too much AI in hiring” is more AI - but pointed at understanding and fit. 

Matthew then met Saaras Mehan. Saaras had been an entrepreneur since he was 11 and went through both EF and Y Combinator with his previous AI sales startup - Kular.

Saaras was one of the most technically gifted people Matthew knew and had an appetite for building so they started Jack&Jill together.

Jack&Jill’s initial version was launched after just an “8-week sprint” and quickly grew their network to 5,000 candidates in the first few months.

Fast forward to today and the tool has:

• 35,000+ users including 15,000+ London professionals across eng/product/marketing/sales/finance.

• 70+ companies already using Jill.

• 10k new jobs searched per hour; one user received a matched role within 15 minutes of talking to Jack.

Market & “Why Now” 📈

Hiring tech is massive and persistent; AI is already embedded across workflows. 🤖

60%+ of UK employers use AI in recruiting; tools that surface strengths can lift interview progression by ~30%; and the UK’s 9M+ inactive adults signal under-matched talent pools waiting to be activated. 

Tailwinds: Rapid LLM gains in voice understanding; employer cost pressure vs. agencies; candidate appetite for coaching and faster feedback. 

Why now: The market doesn’t need another job board - it needs a decision layer that converts messy narratives into matches and fees, end-to-end.

Investment Rationale & My Experience 💭

I’ve also personally used Jack&Jill for landing a startup job & although I didn’t land anything on there, they got me:

✅ 3 first round interviews out of 5 applications

✅ 2 second round interviews

✅ 1 direct referral to Entrepreneurs First

All of these roles were ultra-aligned to my experiences and what I wanted. I’d definitely recommend it to anyone job-hunting right now.

And before you ask, this newsletter is NOT sponsored by them.

Aside from my personal experience, and just doing some calculations on paper - they should already be milking money. 🐄

70 employers × 1 hire/quarter × 10% of avg $80k salary ≈ $2.24M annual fees. Even at half that conversion, it’s a pretty good revenue run-rate for just 6 months in. 💸

With exponential user growth, exponential revenue growth should come pretty soon. I wouldn’t be surprised if they hit $7-10 million in annual revenue by EoY. 🚀

My only concern is that the market they’re in is quite tough - there have been no huge global networked winners in recruitment since LinkedIn and Indeed.

BUT, what I love about Jack&Jill is they’re attacking 2 markets: 

1. Talent marketplaces (LinkedIn/Indeed) 

2. The agency recruitment space (10x bigger than software in recruitment)

This positions them in a much larger market - recruitment on both the enterprise and consumer ends. 📈

Deal Structure 💰

For me, this has been the most exciting investment so far! Matthew’s background is super cool and the rest of the team is super impressive, on-top of the great product. 🚀

In January 2025, Jack&Jill raised a pre-seed from British angels.

💰We’re committing $550k into their seed round at an undisclosed valuation at the founders request.

Just to clarify once more, none of the investments we make as part of Kitsune VC are real - we’re only simulating what investments we’d make if we operated such a fund. 

This is NOT financial advice. ⚠️

Preet’s view🥊

Wail has been talking about Jack and Jill forever, glad he was able to invest.

I am extremely bullish on the idea of interfaceless marketplaces, decisions being tested and simulated using ML/ automation and then connections being made. 📈

Glad they are targeting recruitment, arguably one of the most inefficient marketplace-esque problems to exist. 

Hiring for visawire.ai has been an absolute pain for myself, it took me over 5 months to find our first visa consultant. 

Great founders, a market that desperately needs improvement and a strong solution to it  - I think Wail has hit the nail on the head here (just wonder how much ownership he got).

Before you go 👋 

Thank you for reading.

So far we’ve invested in 7 startups and have vested $3.3 million of our $10 million fund.

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