Chief of staff - Remote

The Flex; San Marino (CA); Remote; USD 120,000 - 160,000; Full time

Job summary

An innovative property management company in California is seeking a Chief of Staff to work closely with the CEO. This role involves driving strategic initiatives, optimizing processes, and aligning teams for global expansion. The ideal candidate is highly adaptable with a strong background in startups or consulting. Enjoy a remote-first environment with competitive compensation and a career-defining opportunity.

Benefits

Competitive compensation

Performance-based incentives

Flexibility and autonomy

Qualifications

• Experience in startups, consulting, investment banking, or real estate.
• Ability to thrive in fast-changing, unstructured environments.
• Willingness to take full ownership of projects.

Responsibilities

• Drive high-impact initiatives across the organization.
• Ensure alignment on strategic goals.
• Help identify and onboard world-class talent.
• Optimize processes for efficiency.
• Lead research and planning for market expansion.

Skills

Analytical skills

Communication skills

Organizational skills

Problem-solving ability

Adaptability

Resilience

Education

Bachelor's degree

Advanced degree

Job description

Overview

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.