At The Flex, we’re on a mission to make renting a home as effortless as buying something on Amazon — fast, seamless, and borderless.
Our proprietary Property Management System (PMS) is transforming how people live and landlords operate — removing friction, cutting fees, and enabling freedom of movement.
We’re assembling a small, elite team of A-Players who thrive under pressure, move fast, and execute with precision. If you want to build a global business from the ground up alongside a visionary founder — this is your opportunity.
🎯 The Role: Chief of StaffAs Chief of Staff, you’ll serve as the Founder & CEO’s right hand — acting as a strategic partner, operator, and execution engine.
This is not a support role — it’s a company-building position. You’ll help set priorities, turn ideas into execution, and ensure the entire organization moves in sync.
You’ll gain exposure across all aspects of the business — operations, technology, finance, expansion, and fundraising — while playing a key role in shaping The Flex’s trajectory as it scales globally.
⚙️ Key ResponsibilitiesStrategic Execution: Drive high-impact initiatives across product, operations, tech, and expansion.
Company Alignment: Turn strategic goals into actionable plans — ensuring every team stays focused on what matters.
Hiring & Talent: Help identify, attract, and onboard world-class talent across functions.
Operational Leadership: Step in where needed to bridge gaps and ensure smooth execution.
Market Expansion: Lead research and operational planning for new city launches and international growth.
Process Optimization: Design systems, workflows, and processes to make the company faster and more efficient.
Cross-Functional Collaboration: Be the connective tissue between departments — driving clarity, accountability, and speed.
Founder Leverage: Act as the CEO’s trusted advisor and execution partner — preparing briefs, managing priorities, and driving decisions forward.
Bachelor’s degree required; advanced degree is a plus.
Background in startups, consulting, investment banking, or real estate.
Exceptional analytical, communication, and organizational skills.
Strong problem-solving ability with bias toward execution.
Highly adaptable — thrives in fast-changing, unstructured environments.
Relentless drive, resilience, and willingness to take full ownership.
High-impact role: Work directly with the CEO on company-defining projects.
Rapid growth: Shape systems, teams, and decisions that will scale globally.
Competitive compensation + performance-based incentives.
Remote-first environment with flexibility and autonomy.
Career-defining opportunity: This is the closest seat to the founder’s table — a launchpad to an executive leadership role or future venture.
You’re looking for a stable, slow 9–5 job.
You prefer talking over doing.
You dislike accountability or ambiguity.
You’re not committed to becoming world-class at your craft.
We’re not building another property company.
We’re building a global ecosystem for flexible living — powered by technology, automation, and ambition.
If you want to build at the intersection of real estate, tech, and scale, and work side-by-side with a founder obsessed with excellence — apply now.
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What We Do
At The Flex, we believe renting a home should be as easy as buying an item from Amazon, that means ensuring our guests have an abundance of choice and flexibility to cancel if their plans change. We aim to help landlords stop paying excessive management fees and help renters live and work comfortably anywhere in the world.
