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 FleekSort, 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.

About the Role

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.

What You'll Do

• 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.

What You Bring

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 own them end to end in a company moving faster.

In both cases, you are:

• Deeply AI-native. You use AI tools instinctively and you're thinking about how to build an AI-powered company, not just automate tasks. You can show the systems and prompts behind how you work.

• A systems thinker. You find the pattern, build the process and get out of the way. You'd rather build something repeatable than be the bottleneck it depends on.

• A sharp communicator. You write clearly, synthesise fast and can represent the founder's credibly to a room of investors or a floor of operators.

• Trusted with everything. You handle sensitive company, people and investor information with total discretion and sound judgment.

• Comfortable at pace. Fleek moves fast and expects the same from everyone. Shifting priorities energise you rather than rattle you.

• Genuinely excited to build the operating system of a company defining a category that didn't exist three years ago.

Nice to Have

• Experience in marketplaces, commerce, or supply chain businesses

• Exposure to fundraising, board management, or investor communications

• Experience working across multiple geographies and time zones

What You'll Get

• Competitive salary

• Generous equity: being on Fleek means you'll own a part of it

• Comprehensive healthcare coverage

• A collaborative team in a lovely office in the heart of East London

• Access to founders. We're a small team and they're heavily involved (and good fun!)

• Exclusive employee discounts to buy on Fleek

• Access to borrow any item from our collection of vintage and reworks in the office

• A disproportionate level of responsibility and the opportunity to drive massive impact

How We Work

Fleek is an in-office company. We're based at Commercial Street, E1 (Liverpool Street / Aldgate East). We operate a fully in-person culture at our office in Shoreditch, with trust-based flexibility. We hire adults and trust them to perform.

The Practicalities

• Location: London HQ, Commercial Street, E1 (Liverpool Street / Aldgate East)

• Work model: On-site, with trust-based flexibility

• Stage: Post-Series B, hyper-growth

• Team: 200 across three geographies

• Culture: High ownership, non-hierarchical, fast-moving. Founder-led with strong opinions loosely held.

Success Metrics

• First 30 days: deep understanding of how Fleek runs today: every team, geography, and founder workflow mapped, with the first version of the operating cadence proposed.

• 3 months: weekly and quarterly business reviews, OKRs and goal-tracking live and holding across all three geographies; investor update cadence owned end to end.

• 6 months: the company brain operational: AI-native knowledge flows in place, decision-making documented and followed through, measurable time returned to the founder's calendar.

• 12 months: the company runs as a system, not a person. The operating rhythm scales with headcount and leadership treats it as infrastructure they can't work without.

Our Values

Five values shape how we work at Fleek:

• Dream Big and Disrupt Yourself: Push the most ambitious version of what you're building. Step out of your comfort zone. Nothing is out of reach.

• Absolute Ownership: The buck stops with you. Drive initiatives to completion. Experiment, learn, persevere. The job isn't done until the job is done.

• Curiosity Leads the Way: Don't accept anything at face value. Ask questions you don't know the answer to. That's how you innovate.

• Talk to the Customer: Deeply understand their challenges, motivations, and ambitions. Every decision starts with the customer at the centre.

• Embrace Diversity: A global team building for a global supply chain. Bring your authentic self and embrace the diversity of everyone you encounter.

Ready to build the infrastructure for the world's fastest-growing fashion economy? If you want to work on genuinely hard problems, with a world-class team, at a company that's tripling annually, we'd love to hear from you.