Senior Executive Assistant / Chief of Staff

Location: Remote (Latin America or South Africa preferred for time zone alignment with U.S. hours)
Employment Type: Full-Time | Independent Contractor
Work Schedule: U.S. Business Hours (EST overlap required)

About the Company

We are a fast-growing real estate investment and development group focused on acquiring, operating, and scaling high-value residential and commercial real estate assets across the United States.

The company operates across multiple areas of the real estate ecosystem including acquisitions, development, asset management, and strategic partnerships. Leadership works at a fast pace and manages multiple initiatives simultaneously, requiring strong operational coordination and disciplined execution.

To support this growth, we are hiring a Senior Executive Assistant / Chief of Staff to work directly with the Founder and executive leadership team.

This role goes beyond traditional executive assistance. The ideal candidate will function as an operational partner to leadership, helping manage priorities, coordinate cross-department initiatives, and ensure critical projects move forward efficiently.

Over time, this role will also take on leadership responsibilities overseeing a team of Executive Assistants, helping build structure, accountability, and operational consistency across the administrative function.

The Role

This position is designed for a highly organized, operationally minded professional who has previously supported C-level executives in high-growth environments, ideally within real estate, private equity, or property development businesses.

You will serve as the right hand to the executive team, helping manage priorities, organize information, coordinate stakeholders, and ensure strategic initiatives are executed.

As the company continues to scale, this role will evolve into a leadership position responsible for managing and coordinating a team of Executive Assistants, ensuring executive support across the organization operates at a high standard.

This is a high trust role requiring discretion, strong business judgment, and the ability to anticipate leadership needs before they arise.

Key Responsibilities

Executive Support

Act as the primary operational support partner to the Founder / Executive team
Manage complex calendars, scheduling, and executive priorities across multiple business initiatives
Coordinate internal and external meetings including investor calls, deal reviews, and leadership meetings
Prepare agendas, notes, and follow-up action items to ensure accountability and execution
Draft high-quality communications including emails, reports, and internal documentation

Operational Coordination

Track and manage strategic projects across the business, including acquisitions, development projects, and operational initiatives
Coordinate between internal teams, partners, vendors, and external stakeholders
Build and maintain operational dashboards, trackers, and reporting systems
Ensure key deadlines and milestones are met across departments

Business Operations Support

Assist with operational planning and business processes across real estate operations
Help organize financial reporting, project updates, and executive dashboards
Support executive decision-making by gathering information and summarizing key insights
Improve internal systems, documentation, and workflows

Executive Assistant Team Leadership (Future Scope)

Provide leadership and operational oversight to a team of up to five Executive Assistants
Establish best practices, processes, and workflows for executive support across the organization
Mentor and develop junior Executive Assistants to improve productivity and performance
Coordinate workload distribution and ensure executives receive consistent, high-quality support
Create documentation, SOPs, and operational playbooks for executive support functions
Monitor performance, provide feedback, and identify areas for improvement across the EA team

Required Qualifications

6+ years supporting C-level executives (Founder, CEO, Managing Partner, etc.)
Experience working in real estate, property investment, development, or related industries
Experience managing complex business operations, projects, or executive initiatives
Demonstrated experience coordinating or managing administrative teams (EA teams, operations staff, or similar)
Exceptional English communication skills (written and spoken)
Strong ability to prioritize, organize, and manage multiple workstreams simultaneously
High level of professional discretion and confidentiality
Comfortable operating in fast-paced entrepreneurial environments

Preferred Qualifications

Experience working in real estate investment firms, development companies, or property management businesses
Experience supporting founders or executives managing multiple ventures or portfolios
Experience building systems, documentation, or operational processes
Familiarity with tools such as:
- Notion
- Monday.com / Asana / ClickUp
- Google Workspace
- Slack
- CRM platforms

Key Traits for Success

Operational leader
You understand how to organize people, priorities, and systems to keep the business moving forward.

Highly organized
You create structure in fast-moving environments and manage multiple executive priorities.

Proactive problem solver
You anticipate issues before they arise and implement solutions.

Strong communicator
You communicate clearly with executives, partners, and internal teams.

Mentor and team builder
You enjoy helping junior team members grow and perform at a higher level.

What Success Looks Like

Within the first 90 days:

Executive priorities are clearly organized and tracked
Leadership receives proactive support and coordination across key initiatives
Meetings and strategic projects are structured with clear follow-through
Internal processes become more organized and efficient

Within 6–12 months:

The Executive Assistant team operates under clear processes and leadership
Junior EAs are more productive and accountable
Executive support across the organization becomes standardized and scalable
Leadership gains significant time back to focus on high-impact decisions

Senior EA / Chief of Staff - 18298