Remote Executive Assistant - CEO Support (Real Estate Experience)

FreedUp are seeking a proactive and detail-oriented Executive Assistant (EA) to support the Founder and CEO of a fast-growing organization building innovative systems. This role is ideal for someone who thrives on structure, accountability, and operational clarity - a professional who can turn complex processes into seamless execution.

We’re a high-performance team with a culture built around accountability, clarity, and efficiency. We’re looking for a proactive, detail-oriented Executive Assistant (EA) to directly support our CEO - helping streamline both his professional and personal operations so he can stay focused on strategy, growth, and leadership.

This is a full-time, remote position that requires strong written communication, organizational excellence, and accountability.

Location: Fully Remote

Job Type: Full-Time

Salary: $800 - $1,600 per month (based on experience)

Requirements

• 3+ years of experience as an Executive Assistant, Operations Coordinator, or similar role supporting senior leadership.
• Excellent written and verbal communication skills.
• Tech-savvy and comfortable working in digital ecosystems (Slack, Notion, Google Workspace, etc.).
• Strong organizational and prioritization abilities.
• Proven ability to manage sensitive information with discretion.
• Background in contracting and compliance concierge services (preferred)
• Experience with client needs assessment
• Statement of work (SOW) creation skills
• Procurement management experience
• Proactive, self-directed, and thrives in an environment with evolving needs.
• Experience managing both business and personal responsibilities for a founder or executive is a plus.
• Basic knowledge of bookkeeping, reporting, or data entry preferred.
• Technical Requirements: Reliable high-speed internet and a modern home office setup.

Key Responsibilities

• Calendar & Inbox Management: Own and optimize the CEO’s calendar and inbox to ensure efficient scheduling, focus time, and timely communication. Coordinate meetings, manage follow-ups, flag priorities, and respond on behalf of the CEO when appropriate. Maintain alignment between professional and personal calendars.
• Business Support: Bookkeeping and accounting support (using QuickBooks), Contracting support for government compliance, Marketing assistance (as secondary capability)
• Process Optimization & SOPs: Document, organize, and improve company workflows and Standard Operating Procedures (SOPs) in Notion. Support the creation of internal systems for accountability, task tracking, and delegation across Trotta’s operations and team structure.
• Administrative & Financial Support: Handle recurring administrative finance processes such as client billing setup, monthly invoices, commissions, and reimbursements. Maintain organized digital records, ensuring accuracy and timeliness in monthly cycles.
• Travel & Event Coordination: Plan and manage travel logistics for the CEO and team, including flights, accommodations, and conference registrations. Build and maintain an annual travel calendar for 8-9 industry events, ensuring smooth execution and detailed itineraries.
• Communication & Coordination: Serve as the central communication link between the CEO, internal team, and external partners. Maintain a professional tone and ensure clear, timely updates across all channels (Slack, Gmail, Notion).
• Reporting & Accountability: Provide structured updates and summaries on priorities, progress, and deadlines. Support time-blocking and productivity systems to help the CEO stay focused on strategic work.
• Compliance & Security Requirements: Ability to maintain cybersecurity protections, Understanding of defense-related compliance certifications, Capability to handle restricted calendar/email access appropriately, Background check clearance.
• Property management: Property management experience, Ability to handle approximately 80% property management-related tasks. Handle assistant property manager-level work and Support property management operations.
• Tools & Communication: Notion, Slack, Google Workspace (Gmail, Calendar, Drive, Docs, Sheets), Todoist or similar task management platforms, Appfolio, LeadSimple
• Preferred Communication: Slack (daily), Zoom (weekly check-ins), email summaries

Benefits

• International experience
• Opportunity to work remotely from anywhere
• Supportive and collaborative team environment
• Learning and development opportunities
• Potential Performance Bonuses
• PTO
• HMO after 3 months