Founding Operator

Founding Operator

London Full-Time 36000 - 60000 £ / year (est.) No home office possible
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At a Glance

  • Tasks: Take ownership of key functions like product, hiring, and operations in a fast-paced startup.
  • Company: Join a dynamic team revolutionising recruitment with AI, aiming to optimise job placements for everyone.
  • Benefits: Enjoy perks like equity, private health insurance, and a brand new MacBook.
  • Why this job: Be part of a high-impact team, learning from experienced founders while shaping your career.
  • Qualifications: Ideal for ambitious problem solvers with a startup mindset and a passion for AI.
  • Other info: Work in-person at Entrepreneurs First offices in London, surrounded by innovators.

The predicted salary is between 36000 - 60000 £ per year.

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.

Who are we and what on earth are we doing?

Our team

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 WilsonCo-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 MehanCo-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 AthillCMO – 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 CoopeFounding 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 TandonFounders 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.

What are we doing?

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.

Meet Jack & Jill

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 moving at breakneck speed

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:

Who are we looking for?

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.

Our Operating Approach:

  • Mindset: First-principles thinking, extreme ownership, intellectual honesty.

  • Method: You diagnose problems, build v1 solutions manually, then automate and scale.

You’ll be a great fit if:

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.

This role isn\’t for you if:

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!

And there’s also the perks…

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

How do I join the journey?

  1. 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.

  2. Intro Call with Matt – a 30-min chat about your ambitions and to learn more about our biggest challenges.

  3. 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.

  4. Offer will be made and you’ll join us on the journey.

#J-18808-Ljbffr

Founding Operator employer: webAI

At Jack & Jill, we pride ourselves on being an exceptional employer that fosters a high-performance culture in the heart of London. As a Founding Operator, you'll have unparalleled opportunities for growth and ownership, working alongside a team of elite professionals dedicated to redefining recruitment through innovative AI solutions. With competitive salaries, generous equity options, and a supportive environment that prioritises your well-being, we are committed to helping you achieve your career-defining legacy while making a meaningful impact.
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Contact Detail:

webAI Recruiting Team

StudySmarter Expert Advice 🤫

We think this is how you could land Founding Operator

✨Tip Number 1

Familiarise yourself with the latest trends in AI and how they can be applied to operational processes. Being able to discuss innovative uses of AI during your conversations will show that you understand the company's mission and are ready to contribute.

✨Tip Number 2

Network with current or former employees of StudySmarter or similar startups. They can provide insights into the company culture and the specific challenges faced by a Founding Operator, which can help you tailor your approach during discussions.

✨Tip Number 3

Prepare to demonstrate your problem-solving skills through real-world examples. Think of situations where you've had to diagnose issues and implement solutions quickly, as this aligns with the fast-paced environment at StudySmarter.

✨Tip Number 4

Showcase your ability to work collaboratively in a team setting. Highlight experiences where you've contributed to a team's success, as being a low-ego team player is crucial for the role of a Founding Operator.

We think you need these skills to ace Founding Operator

First-Principles Thinking
Extreme Ownership
Intellectual Honesty
Problem Diagnosis
Manual Solution Development
Automation Skills
High-Level Strategic Thinking
Execution with No-Code Tools
Spreadsheet Proficiency
Adaptability
Ambitious Overachievement
Team Collaboration
Effective Communication
AI Proficiency
Experimentation with New Tools

Some tips for your application 🫡

Understand the Role: Before applying, make sure you fully understand the responsibilities of a Founding Operator. Familiarise yourself with the key functions mentioned in the job description, such as GTM, product development, and operations.

Tailor Your CV: Craft your CV to highlight relevant experiences that align with the role. Focus on your problem-solving skills, any startup experience, and instances where you've demonstrated ownership and initiative.

Write a Compelling Cover Letter: In your cover letter, express your passion for the role and the company. Share specific examples of how your background makes you a great fit for the fast-paced environment and the challenges outlined in the job description.

Showcase Your AI Knowledge: Since the role involves working with AI technologies, mention any relevant experience or projects where you've used AI tools. This will demonstrate your capability to thrive in an AI-driven environment.

How to prepare for a job interview at webAI

✨Show Your Problem-Solving Skills

As a Founding Operator, you'll need to demonstrate your ability to diagnose problems and create solutions quickly. Prepare examples from your past experiences where you've tackled complex challenges, showcasing your first-principles thinking and hands-on approach.

✨Emphasise Your Adaptability

This role requires flexibility and the ability to pivot between tasks rapidly. Be ready to discuss how you've successfully managed shifting priorities in previous roles, and highlight your comfort with ambiguity and chaos.

✨Demonstrate Your Team Player Attitude

Communication and collaboration are key in a small team environment. Share instances where you've worked effectively within a team, emphasising your low-ego approach and how you’ve helped elevate those around you.

✨Be Prepared to Discuss AI Tools

Since the company values AI proficiency, come equipped with knowledge of AI tools you've used to enhance productivity. Discuss specific examples of how you've leveraged technology to solve problems or improve processes in your previous roles.

Founding Operator
webAI
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  • Founding Operator

    London
    Full-Time
    36000 - 60000 £ / year (est.)

    Application deadline: 2027-07-27

  • W

    webAI

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