Chief of Staff

Can you help us fix the world's most broken supply chain?

The fashion industry produces over 100 billion garments a year. 60% end up in landfill, not because people don't want these clothes, but because the supply chain for getting secondhand fashion from donation to resale is completely offline, manual, and broken.

Fleek is fixing this.
Our mission is to make secondhand the first choice. We're building the infrastructure powering the global secondhand clothing trade, through a B2B marketplace and the AI systems digitising the supply chain behind it

Through Fleek, vintage stores, online resellers, and retail buyers source graded secondhand inventory directly from wholesalers and rag houses across multiple countries. Our key enabler is Fleek Sort, an AI model fine-tuned on secondhand fashion, that can grade, price, and categorise items with just a photo, turning what has historically been an opaque and manual trade into a structured, searchable, and tradable global inventory layer.

Since 2022, we've saved 9 million items from landfill and tripled in size year-on-year. We've raised ~$50M from a16z, Y Combinator, HV Capital, and others, and have recently closed our Series B. Our advisors and private investors include operators behind Depop, Shopify, and Postmates.

Today, we serve thousands of resellers and retailers across the UK, Europe, and the US. With the secondhand fashion market projected to reach $350B by 2027, Fleek is building the AI-native operational and financial backbone for secondhand commerce globally.

We're looking for people who want to build something that matters, and move fast doing it. Sound good? Keep reading.

We're building Fleek's AI-native operating engine, and we need the person who runs it. As Chief of Staff, you'll operate closer to a COO than a traditional chief of staff: building the drumbeat of the company, keeping a 200-person organisation aligned across three geographies and ensuring the operating rhythm holds as we scale fast.

The timing matters. The operating structure this role builds is the structure Fleek scales on: if it isn't in place now scaling effectively becomes very difficult. You won't inherit a rhythm, you'll create it, and you'll do it AI-first: this is about building an AI-powered company, not automating a traditional one.

This is a senior leadership role with real ownership over how this company thinks, communicates and executes. Our founders are experienced and capable; your job is to multiply them.

• Build the company brain: design our AI-native information architecture and knowledge flows so the right people know the right things at the right time, across every team and geography.

• Own the operating rhythm: build and run the cadence that doesn t exist today: weekly and quarterly business reviews, OKRs, goal-tracking and cross-functional alignment across three geographies.

• Create founder leverage: make the founders meaningfully more productive and effective through hyper-growth: owning their priorities, filtering what reaches them and driving what leaves their desk to completion.

• Run investor relations: own the cadence and quality of investor updates, keeping our backers (a16z, YC, HV Capital and others) close and informed as we scale.

• Build communication infrastructure: define how decisions get made, documented, communicated and followed through at scale, internally and externally.

• Turn patterns into systems: wherever the company repeats itself, find the pattern, build the process or the agent that runs it and get out of the way.

• Be the connective tissue: spot misalignment between teams and geographies before it becomes a problem and fix it without being asked.

You're one of two profiles:

Ex-founder, operator at scale. You've built something yourself and you've worked inside a fast-scaling company. You know what 200 people looks like from the inside, you've seen what breaks and you know how to stop it happening.

Senior operator ready for a bigger seat. You've been in a chief of staff, strategy, or senior ops role at a high-growth startup or scaleup. You've built the operating systems companies run on and you're ready to…