The posting
Every person in the right job. Every company hiring the best person for every role. That's what our agents, Jack and Jill, exist to do - and in doing it, we're reshaping a marketplace. We’re looking for a finance leader who can mature our commercial operations with the scale of our ambition.
We’ve raised $60m within a year, most recently a $40m raise led by Air Street Capital with participation from Creandum and Madrona. We are a small, AI-native, high-leverage team, and proven PMF, with over 400,000+ warm candidates in the network. Currently ninety percent of client acquisition is through an inbound self-serve motion, with no human in the loop. We are in London, and more recently San Francisco and New York.
THE PROBLEM WE'RE SOLVING
Our career is one of the most important things in our life, with each move a far-reaching decision, but there's no-one offering help, fairly, and for free. When taking the next step in their career, most people can only access 1% of the available options.
On the flip side, recruitment is insanely inefficient for companies. Hiring the right people is the most consequential thing a company can do, yet AI has for the most part failed to make things better.
Jack is an AI agent that finds your next job and helps you land it. Jill is an AI agent for hiring already helping thousands of companies make their next great hire.
Both are connected and working together to deeply understand you - making direct introductions, and saving you from sending, or reviewing, applications.
The last major technological shift in recruitment created LinkedIn. The next great shift is here. The world of work is changing faster than we expected. Finding the right job, or the right person, has never mattered more. Or been more complicated. Soon, everyone will have an AI agent managing their career, and every company will have an AI agent helping them hire. Creating a fair and frictionless job market for the first time.
Our mission: end the era of wasted human potential. We believe the only way to fix the system is to rebuild both sides and make them work together.
WHAT DO WE NEED TO DO?
You’ll build the financial backbone that takes Jack & Jill through $100m+ in revenue. We need a hands-on, high-agency leader to build a lean, AI-first finance function who can also act as a thought partner to the CEO and the rest of the company including on the complex economics of scaling an inference heavy marketplace.
- FP&A and unit economics. Own forecasting, planning and budgets, and the unit economics across both sides of the marketplace. Finding the balance between aggression and discipline.
- Pricing and commercial strategy. Build the pricing models and shape how we make money as we scale.
- Board and investor reporting. Produce board-quality reporting and manage our relationships with existing investors.
- Fundraising. Work with the CEO on the next and subsequent rounds, from the data room and the model, to supporting in investor conversations.
- Cash and controls. Own cash, and own or directly oversee close, accounting, audit and tax.
- An AI-first function. Choose the tools, automation and dashboards that let a small finance team do the work of a much larger one.
WHO WE ARE AND HOW WE GET STUFF DONE
You will join one of the most talent-dense teams in the world: ex-founders (two thirds of the team), former CTOs, published academics, thought leaders, hypergrowth veterans, and people with multiple exits, often in the same person. Everyone is an overachiever, and we all know what it takes to win.
We move at lightning-speed, ship daily, have agents that can do as much of the lifting as our humans, and we work exceptionally hard.
We also work in person - we’re 5 days a week together in our office in Shoreditch alongside offices in SF and NYC.
OTHER USEFUL INFO
OUR TEAM
You'll report to Matt, and work alongside a world-class founding team.
Matt Wilson https://www.linkedin.com/in/matthew-wilson-671a757a/, Co-founder & CEO
3x founder. Founded Omnipresent, the fastest-growing Entrepreneur First company of all time (0 to $600M valuation in 3 years, exited to Deel).
Saaras Mehan https://www.linkedin.com/in/saaras-mehan/, Co-founder & CTO
Second-time founder, YC/EF/Cambridge/Microsoft Research alum. Grew Kular.ai http://Kular.ai (YC W22) from $0 to $3M ARR in one year.
K. Fujita https://www.linkedin.com/in/fujitak/, B2B GTM Lead
2x $0-25M, 2x exits. Ex-VP Sales & Marketing at Omnipresent, ex-Entrepreneur First founder. Leads Jill acquisition.
John Wong https://www.linkedin.com/in/johnwong00/, Startup Operator working on finance and operations, with experience scaling high-growth startups/scale-ups including early hire at Tractable (EF), Moove and Bird
Tom Robinson https://www.linkedin.com/in/t-rob/, Currently leading all B2C and B2B marketing. Specialist across Growth, Data & Product
Ex-VP Global Marketing at Deliveroo, where he spent 7 years building and leading a 100+ person function across data science, analytics engineering, and marketing. Ex-PwC. Cambridge MPhil Economics.
Ed Steele https://www.linkedin.com/in/ed-steele/, Founding Operator currently working on GTM Architecture, Product, and CS
Co-Founder of Hoxton Farms. A company he took to a team of 50, Thought Machine ML Engineer and Oxford University Tutor.
Meet the full team. https://www.jackandjill.ai/about-us
🎯 YOU'LL BE A GREAT FIT IF
- Been the number one finance person, owning the whole function, at a company doing $50–200M+ in revenue, or through a step-change to that scale. That means FP&A, forecasting, unit economics, cash, and close and accounting (or direct oversight of them).
- Produced board-quality reporting and been hands-on in raising capital.
- You've taken a VC backed tech start up from early stage through growth+, and worked with top-tier European and US investors.
- You’ve run finance across a range of complex commercial models, not just subscription based SaaS, and operated across multiple geographies.
- You have strong commercial instincts coupled with a rigorous analytical approach
- You have a real appetite for an early-stage, high-agency, commercially aggressive seat.
- You're genuinely AI-native and excited to use it as a force multiplier - You’ve worked deep in the data yourself, in SQL, spreadsheets and dashboards, with AI tools already a core part of how you work.
Bonus if you’ve worked with marketplaces, or founded your own company in the past.
🚫 THIS ROLE ISN'T FOR YOU IF
- 🧱 You need a large team to operate.
- 🖥️ You want a predictable 9-to-5. We're building fast and the work is intense. We respect life outside work, but we do what it takes to win.
🎁 AND THERE'S ALSO THE PERKS...
We have fun, work hard, and do great work. We don’t want people to have to compromise on the things that help them do that.
- 💰 Choose your own cash : equity split
- 🏥 Private health insurance with Bupa
- 🚗 An Uber home if you're working late
- 🍲 Deliveroo dinners in the office
- 🧽 Fortnightly home clean
- 📍 In-person, 5 days a week at our London office in Shoreditch Exchange, surrounded by delightful, smart people.
📌 HOW DO I JOIN THE JOURNEY?
- Talk to Jack and apply via the link on our About page https://www.jackandjill.ai/about-us.
- Intro Call with Kate. A 30-min chat about your ambitions and to learn more about our biggest challenges.
- Call with Matt, our CEO and hiring manager. Do you align on the fundamentals?
- Work Trial. A paid working session with our founding team. We'll give you a real, complex problem we're facing today and work alongside you to solve it.
- Offer made. You join the journey.
