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Chief of Staff

FleekLondonOperations
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Salary
Not listed
Job type
Full-time
Posted
3 Aug 2026
Status
Open · checked 7d ago

About this role

Role Overview

Fleek is hiring a Chief of Staff in London to help build and run the company's AI-native operating engine. This senior leadership role works closely with the founders to establish the internal rhythm, communication infrastructure, and operating structure as the organization scales rapidly across multiple geographies. This position suits an experienced operator or former founder ready to take on massive ownership in a fast-paced environment.

Key Responsibilities

Build the company brain by designing AI-native information architecture and knowledge flows for teams across every geography.
Own the operating rhythm, including weekly and quarterly business reviews, OKRs, goal-tracking, and cross-functional alignment.
Create founder leverage by prioritizing tasks, filtering inbound requests, and driving initiatives to completion.
Run investor relations by managing the cadence and quality of updates for backers like a16z, YC, and HV Capital.
Build communication infrastructure that defines how decisions are made, documented, communicated, and executed internally and externally.
Turn recurring patterns into systems, processes, or automated agents to remove bottlenecks.
Serve as connective tissue by identifying and resolving misalignment between teams and geographies proactively.

Requirements

Background as a former founder with experience scaling inside a fast-growing company, or as a senior operator in a chief of staff, strategy, or senior ops role at a high-growth startup or scaleup.
Deeply AI-native mindset, with the ability to use AI tools instinctively and demonstrate the systems and prompts behind daily work.
Systems thinker who prefers building repeatable processes over becoming an operational bottleneck.
Sharp communication skills with the ability to write clearly, synthesize information fast, and represent leadership credibly to investors and operators.
Absolute discretion and sound judgment when handling sensitive company, people, and investor information.
Comfortable working at a rapid pace with shifting priorities in a high-ownership culture.

Nice to Have

Experience working in marketplaces, commerce, or supply chain businesses.
Exposure to fundraising, board management, or investor communications.
Experience working across multiple geographies and time zones.

Skills and Tools

RAG
AI-native productivity and workflow tools
OKR and goal-tracking systems
Business review frameworks

Salary and Benefits

Competitive salary
Generous equity ownership in Fleek
Comprehensive healthcare coverage
Collaborative team based in an office in the heart of East London
Direct access to the founders and leadership team
Exclusive employee discounts for purchases on Fleek
Access to borrow items from the office vintage and rework collection

About the Company

Fleek is building the infrastructure that powers the global secondhand clothing trade through a B2B marketplace and AI systems that digitize the supply chain. Since 2022, the company has saved 9 million items from landfill, tripled in size year-on-year, and raised approximately $50 million from prominent investors including a16z, Y Combinator, and HV Capital. Operating out of an office on Commercial Street in Shoreditch, London, Fleek serves thousands of resellers and retailers across the UK, Europe, and the US.

How to Apply

To apply for this position, please visit the official Fleek careers page and submit your application online.

Skills and tech stack

RAG

Questions candidates ask

Where is the Chief of Staff role located?

The role is based at Fleek's London headquarters on Commercial Street in Shoreditch, operating as an in-office position with trust-based flexibility.

What type of experience is required for this role?

Candidates must either be former founders with experience inside a fast-scaling company or senior operators who have held chief of staff, strategy, or senior ops roles at high-growth startups.

What does being 'AI-native' mean for this position?

It means using AI tools instinctively, building an AI-powered company rather than merely automating traditional tasks, and being able to show the systems and prompts used in daily work.

What are the success metrics for the first year?

Success metrics include mapping workflows and proposing an operating cadence in 30 days; establishing reviews, OKRs, and investor updates in 3 months; deploying the company brain and AI knowledge flows in 6 months; and having the company run as a reliable system by 12 months.

What perks and benefits are included?

Benefits include a competitive salary, generous equity, comprehensive healthcare, office perks like vintage clothing borrowing and discounts, and direct access to founders.

Ready to apply?

The application is on the official Fleek careers page.

Apply on company site