Jack & Jill
Chief of Staff (+ Equity) at Fleek
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This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.
She will pick the best candidates from Jack's network.
The next step is to speak to Jack.
Job Title
Chief of Staff
Salary
Not Disclosed + Equity
Company Description
Fleek is a ~$50M Series B London marketplace backed by a16z and Y Combinator building the AI-native infrastructure for the global secondhand clothing trade.
Job Description
As Chief of Staff, you will build and run Fleek’s founder’s office, designing the operating system for a 200-person global company scaling across three geographies. You will own the rhythm of business, investor relations, and AI-first knowledge flows, acting as a force multiplier for the founders while scaling the company's internal brain.
Location
London, UK
Why this role is remarkable
- Join a high-growth, post-Series B marketplace backed by top-tier investors like a16z, Y Combinator, and HV Capital at a critical scaling inflection point.
- Build an AI-native company operating system from scratch, designing how a global team of 200 communicates and executes across London, Karachi, and Bangalore.
- Have direct impact on the $350B secondhand fashion market, helping Fleek triple its growth annually while diverting millions of items from landfills.
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What You Will Do
- Design and own the company’s operating rhythm, including OKRs, quarterly business reviews, and cross-functional alignment across three international offices.
- Architect AI-native information flows and knowledge management systems to ensure seamless decision-making and transparency across the entire organization.
- Manage investor relations end-to-end, maintaining high-quality communication with backers like a16z and YC while multiplying the founders' decision throughput.
The ideal candidate
- Proven experience scaling a high-growth company from 50 to several hundred people in operations, strategy, or business leadership roles.
- An AI-native systems thinker who instinctively uses and builds AI tools to automate patterns and optimize complex organizational workflows.
- Exceptional communication and synthesis skills with the ability to navigate sensitive investor relations and lead cross-functional teams with total discretion.
Who are Jack & Jill?
Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
Get help with your application
Your very own career expert that helps elevate your application to the next level.
And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
How does this work?
- Jack's an AI agent for job searching and career coaching. He works for you.
- Jill is the AI recruiter working for the company. She recruits from Jack's network.
- If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
We never post fake jobs
This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.
Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.
We appreciate this can make them look a bit suspect, but there isn't much we can do about it.
Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.
“It took my CV and asked me questions relevant to understanding what kind of jobs to suggest for me. Suggestions were almost perfect. Jobs were exactly what I’ve been looking for.”
Jessica, London
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