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webAI is seeking a Founding Operator to drive key initiatives and solve complex challenges. This multifaceted role will involve collaborating closely with leadership to shape the company’s future, providing hands-on support across product, sales, and operations. Ideal candidates will demonstrate high intelligence, adaptability, and a proactive approach in a fast-paced environment, integral to shaping the company's legacy. Join us at the Entrepreneurs First offices in London and contribute to a transformative journey in AI-driven recruitment.
We’re hiring a founding operator to get hands-on ownership across our most critical functions—driving initiatives in GTM, product, hiring, fundraising, operations. One week you’ll be setting up a new support process, the next you could be building a new outbound sales engine or launching a new product. It's the ultimate tour of duty for a future founder or a high-impact operator looking to build a career-defining legacy.
AI enables small teams to achieve incredible things: building wonderful products, and huge businesses. We’re doing the same.
We’re building the most talent-dense team in Europe. We’ve got impressive track records, but Jack & Jill will be the defining achievement of our careers.
Matthew Wilson –Co-Founder and CEO – 3x founder. Founder/co-CEO at HRTech Omnipresent, the fastest growing Entrepreneur First company of all time (0 → $600m valuation in 3 years).
Saaras Mehan – Co-Founder and CTO – Second-time Founder and {YC, EF, Cambridge, Microsoft Research}-alum Grew Kular.ai (YC W22) from $0 → $3m ARR in one year.
Franky Athill – CMO – Serial startup/scaleup CMO. Multiple 0 -> double digit ARR journeys. Most recently founding CMO at Fyxer.ai - built growth engine from 0 -> $10m ARR in 15 months.
Sam Coope – Founding Engineer – 4x founding Engineer at AI startups. Built the world’s first fully neural voice agent for customer service at PolyAI in 2018. 11 papers and 5 patents published in conversational AI.
Arya Tandon – Founders Associate – 3x start-up operator and ex-founder (raised £1.5m pre-seed). Ex-VC who ran Notion Capital's high-velocity pre-seed investing. Built a London-based community for future founders with 1k+ members.
You? – Founding Operator – A smart, product-focused, ambitious, fast-moving, high-agency team player.
Imagine a world where every person is in their optimal job – doing their best work, fulfilled and impactful – and every company has the optimal people working for them, driving innovation and success. We’re a long, long way from that today.
It’s ridiculous that processes so fundamental to our lives and companies are this terrible.
It isn't a problem that can be solved by adding AI to existing workflows. We need to think from first principles about what is possible with today and tomorrow’s technologies.
Jack is an AI that gets to know you deeply, what you’re great at and what you want out of your career. He then works to make that a reality – finding the best fit public job listings as they come up, supporting with applications, interview prep, and moral support.
He also works together with his partner Jill to find off-market opportunities and introduce you directly to companies, just like a recruiter would.
Jill is an AI that spends time with hiring managers and talent teams to really understand their company, their open roles, and who will thrive there. She works with Jack to find great fit people, like a headhunter with 1000x the network.
Jack & Jill will not just disrupt the existing recruitment software market, but also the 10x bigger recruitment services market (e.g. agency recruiters).
You can chat to Jack here.
We’re just over 3 months old, we’ve built two remarkable products, have thousands of users, paying customers and a spectacular early team. The technology is ready and 10x better than the status quo – we need to build and execute at a relentless speed to build on this early momentum and bring it to the world as fast as we can.
We have thousands of users having incredible experiences with Jack & Jill:
We’re looking for a Founding Operator to join our Founder's Office. You won't be in a box. You'll be a force multiplier for the entire company, working directly with the CEO to solve our highest-leverage challenges and turn ambitious ideas into reality in hours, not weeks.
We’re aiming to build one of the fastest growing companies of all time, and as such, the needs of the company change weekly. One week you’ll need to swarm on running a process manually, before automating it and moving onto the next fire.
While we're open to exceptional people from any background, we've found that people who thrive in this role often have a specific DNA. You could be an ex-founder who knows the startup grind, an aspiring founder looking to learn from a world-class team, a former tier-1 consultant with some startup operating experience, or a high-performing Founders Associate ready for more ownership.
Mindset: First-principles thinking, extreme ownership, intellectual honesty.
Method: You diagnose problems, build v1 solutions manually, then automate and scale.
You're a high-agency, 'full-stack' problem solver. You have the raw intelligence to get to the core of any problem, fast. You can flex seamlessly from high-level strategy to rolling up your sleeves and executing with no-code tools, a spreadsheet, or just sheer grit. You don't need a playbook; you find a way to get it done.
You're an ambitious overachiever. You have a history of holding yourself to an exceptionally high bar and excelling, whether academically, professionally, or personally. You are driven by a desire to be part of an elite team doing career-defining work.
You are a low-ego team player and a great communicator. We believe a small team of A-players is exponentially more than the sum of its parts. You communicate with clarity, and you understand that we only win together. You make the people around you better.
You are an AI power user. You're not just curious about AI; you actively use it to 10x your own output and are constantly experimenting with new tools and workflows. You believe, as we do, that AI enables small, elite teams to achieve extraordinary things.
️ You want a predictable 9-to-5. We are building an extremely ambitious company at lightspeed. The work is intense and demanding. While we value your life outside of work, we are a team that does what it takes to win, and that often means working long and hard.
You need a highly-structured environment. We are in the ambiguous, chaotic, and thrilling phase of 0-to-1. You will be creating the structure, not operating within it. If you need a manager to tell you what to do, this is not the right place for you.
You think some work is beneath you. There is no room for ego. One day you'll be building an investor deck, the next you'll be doing manual data entry to unblock a customer. We all do the unglamorous work required to succeed.
We’re working in-person at the Entrepreneurs First offices in London, so you’ll be surrounded by builders!
We’re building a high-performance environment. You’ll work hard, and we want to clear your plate to make sure that you have everything you need to be able to perform at your very best!
Above market salary
Generous equity 0.1% - 0.5%
Private health insurance
An Uber home if you’re working late
Dinner in the office
Fortnightly home clean
Brand new MacBook
Apply by speaking to Jack, and sending an email to our founder/CEO Matt Wilson on careers@jackandjill.ai, telling him why you’re interested.
Intro Call with Matt – a 30-min chat about your ambitions and to learn more about our biggest challenges.
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 will be made and you’ll join us on the journey.