Remote Executive Assistant - CEO Support (Real Estate Focused)

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)

• 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

• 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