Chief of staff - Remote

About The Flex

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 Staff

As 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 Responsibilities

• Strategic 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.
  
  

What We’re Looking For

• 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.
  
  

Why Join The Flex

• 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.
  
  

Do Not Apply If

• 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.
  
  

The Flex

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.