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.
Chief of Staff at Fleek
We’re building the AI-native infrastructure for the $350B global secondhand clothing trade and need a systems-focused leader to architect our company’s operating rhythm. You’ll multiply our founders, own investor relations, and design the information architecture for a 200-person team across London, Karachi, and Bangalore. If you’ve scaled high-growth startups or founded your own company and want to build an AI-first organization that’s tripling year-over-year, this is your chance to define a category and save millions of garments from landfills.
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Location
London, United Kingdom
Compensation
Not Disclosed + Equity
Company
Fleek
Role overview
Technology100 employees
Fleek is a global online marketplace specializing in wholesale second-hand fashion. The platform connects retailers and resellers with verified vintage wholesalers around the world, making it easier to source high-quality used clothing in bulk. Fleek addresses the fragmented and often offline supply chain of vintage apparel by providing a transparent, secure, and scalable solution for both buyers and sellers. Founded in 2021, Fleek serves thousands of resellers and retailers in over 70 countries, moving millions of vintage clothing items from a vast network of wholesale suppliers. The company is backed by prominent investors, including Y Combinator, and has raised significant funding to expand its market reach and technical capabilities.
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.
Who this is a fit for
- 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.
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.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.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.
I recruit from Jack’s network and make the intro when I spot a great match.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.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
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 your profile’s a match and Fleek wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.