Executive Assistant

POSITION OVERVIEW

The Executive Assistant (EA) provides high-impact strategic, operational, and administrative support to the CEO and Chief of Staff across multiple companies. Serving as a trusted partner and extension of executive leadership, this role ensures seamless execution of priorities, disciplined follow-through, and effective cross-functional coordination.

The EA operates with a high degree of autonomy and discretion, managing complex workflows, sensitive information, and competing priorities in a fast-paced, high-trust environment. This role is critical to maintaining executive focus, organizational alignment, and operational momentum.

KEY RESPONSIBILITIES

Executive Partnership & Strategic Support

• Act as a trusted partner to the CEO and Chief of Staff, managing day-to-day operational priorities to enable focus on strategic leadership.
• Anticipate executive needs, assess dependencies, and proactively resolve issues before escalation.
• Support executive decision-making through structured information management, task tracking, and consistent follow-through.

Complex Calendar & Meeting Management

• Own sophisticated, multi-stakeholder calendar management across internal teams, external partners, and multiple entities.
• Coordinate scheduling across time zones, organizations, and senior leadership levels, including highly confidential meetings.
• Drive meeting logistics, confirmations, and outcomes through proactive communication and follow-up.

Documentation, Compliance & Confidential Information Management

• Manage end-to-end workflows for sensitive documentation, including NDAs and related compliance materials.
• Partner closely with legal teams, executives, and external stakeholders to ensure accurate, timely execution.
• Maintain organized documentation systems with appropriate access controls.
• Serve as a trusted gatekeeper for confidential, proprietary, and executive-level information.

Cross-Functional & Cross-Company Coordination

• Act as a central point of coordination between executives, internal functions (legal, marketing, IT, operations), and external stakeholders.
• Translate executive direction into clear action items, ownership, and timelines across teams.
• Ensure alignment, accountability, and progress across multiple companies and workstreams.

Operational Oversight & Task Execution

• Track, prioritize, and manage executive-level initiatives, tasks, and deliverables.
• Maintain visibility into progress, risks, and blockers; escalate thoughtfully and at the right time.
• Drive execution to completion while balancing competing priorities and shifting demands.

Process, Workflow & Information Management

• Maintain executive notes, priority lists, and task-tracking systems to ensure clarity and continuity.
• Identify opportunities to streamline workflows, reduce friction, and improve operational efficiency.
• Support light process design and continuous improvement initiatives as needed.

Special Projects & Administrative Leadership

• Lead and support ad hoc projects, operational initiatives, and executive requests.
• Manage administrative responsibilities with ownership, accountability, and minimal oversight.
• Adapt quickly to changing priorities while maintaining professionalism and attention to detail.

Qualifications

• Extensive experience supporting senior executives in a Senior Executive Assistant, Executive Assistant, or operations-focused role.
• Proven ability to operate independently with sound judgment, discretion, and confidentiality.
• Exceptional organizational, prioritization, and problem-solving skills.
• Strong written and verbal communication skills with executive presence.
• Demonstrated experience coordinating across departments, leadership teams, and external partners.
• High proficiency with calendar management tools, documentation systems, and productivity platforms.

Core Competencies

• Executive partnership and strategic thinking
• Ownership, accountability, and follow-through
• Stakeholder management and influence
• Operational rigor and attention to detail
• Adaptability, resilience, and sound judgment

Role Positioning

This role extends beyond traditional executive support, functioning as an operational partner who drives coordination, execution, and alignment across leadership and the organization. While the position does not include direct people management, it carries significant influence, responsibility, and trust.

About Freedom Family Investments

Freedom Real Estate Group and its Family of Companies consists of three diverse organizations, each with its unique purpose and mission. As an Executive Assistant, you will have the opportunity to contribute to the growth and success of each of these entities, making every day a new and exciting challenge.

Benefits:

- Paid Time Off (PTO) - 240 hours annually

- Paid US Holidays

- Team member rewards program

- Opportunities for growth and advancement within our organization

Job Type: Full-time

Expected hours: 40 per week

Benefits:

• Opportunities for promotion
• Work from home

Application Question(s):

• Do you have prior experience supporting senior executives (e.g., CEO, President, Founder) in a Senior Executive Assistant, Executive Assistant, or operations-focused role?
• Are you comfortable working independently and making decisions using sound judgment while maintaining strict confidentiality?
• How do you manage competing priorities and deadlines in a fast-paced environment?
• Have you coordinated work across multiple departments, leadership teams, or external partners?
• Which tools or systems have you used regularly for calendar management, documentation, and productivity?

(e.g., Google Workspace, Microsoft Outlook, Notion, Asana, ClickUp, etc.)

Work Location: Remote