Chief of Staff at Real Estate Investment & Education Company (Remote, SEA-Based)

Paired is a global recruiting agency that pairs remote work with top-tier talent. We help individuals from around the world connect with great companies that are looking for their specific skill set. Our mission is to provide great jobs to talented people, no matter where they are located.

About Our Clients

Our client is a results-driven real estate investment and education company that helps military and civilian investors build wealth through shared living strategies and VA-backed real estate. Through its community and consulting programs, the company provides investors with practical insights, resources, support, and access to an experienced network of real estate investors and entrepreneurs.

They are looking for a Chief of Staff to work closely with leadership and help drive operational execution across the business. This is a high-ownership role for someone who can turn priorities into action, keep cross-functional initiatives moving, identify opportunities to improve how the business operates, and bring structure to a fast-moving environment.

Key responsibilities

• Partner closely with leadership to translate priorities and goals into clear action plans and ensure consistent follow-through.
• Own and coordinate cross-functional projects, keeping stakeholders aligned on priorities, timelines, deliverables, and next steps.
• Drive day-to-day operational execution across the business and identify opportunities to improve processes, workflows, and team efficiency.
• Prepare for and follow up on leadership meetings, ensuring decisions, action items, and commitments are clearly documented and followed through.
• Monitor key initiatives and business priorities, proactively identifying blockers, risks, and areas requiring leadership attention.
• Coordinate communication and collaboration across teams to ensure projects continue moving forward effectively.
• Develop and maintain systems, processes, and documentation that improve organizational efficiency and accountability.
• Use AI tools and automation where appropriate to streamline workflows, reduce manual work, and improve operational effectiveness.
• Take ownership of ad hoc strategic and operational initiatives as business needs evolve.

Requirements

• 5+ years of experience in Chief of Staff, Operations, Executive Assistant, Business Operations, Project Management, or a similar role with significant ownership and cross-functional exposure.
• Proven experience managing and driving cross-functional projects from planning through execution.
• Strong organizational and project management skills, with the ability to manage multiple priorities and stakeholders simultaneously.
• Demonstrated ability to work independently, anticipate needs, solve problems, and operate with minimal oversight.
• Strong written and spoken English, with the ability to communicate clearly with executives and cross-functional teams.
• Strong judgment and attention to detail, with the ability to distinguish between high-priority and low-priority work.
• Comfortable working in a fast-paced, remote environment and taking ownership beyond assigned tasks.
• Working knowledge of AI tools and their practical application to business workflows.
• Experience with automation tools such as Zapier, Make, n8n, or native integrations is preferred.
• Willingness and ability to work full-time hours with complete overlap with U.S. Pacific Time (PST).

Benefits

• Competitive USD compensation based on experience, skill level, and country of residence.
• Remote flexibility – Work from anywhere while collaborating with a global team.
• Opportunity to work closely with leadership and take meaningful ownership of business operations and cross-functional initiatives.
• High-autonomy environment with opportunities to improve processes, systems, and how the business operates.