Executive Assistant

Park Square Homes; Orlando (FL); On-site; USD 55,000 - 75,000; Full time

Job summary

Park Square Homes is seeking a talented Executive Assistant to support the CEO in a fast-paced and entrepreneurial environment. Responsibilities include managing complex schedules, preparing executive-level materials, and facilitating communication across teams. Ideal candidates are proactive problem-solvers with strong organizational skills and a background in supporting senior executives.

The position offers opportunities to engage in special projects and assist with event planning. A high school diploma is required, with preference for additional qualifications or background in real estate.

Qualifications

• Minimum of 3–5 years of experience supporting senior executives.
• Experience in entrepreneurial or growth-oriented environments preferred.
• Prior experience in real estate or homebuilding is a plus.

Responsibilities

• Manage the CEO’s complex calendar and scheduling.
• Prepare materials to support executive decision-making.
• Facilitate information flow between stakeholders.
• Plan and execute executive-level meetings and events.
• Support family office activities and select personal matters.

Skills

Proactive problem-solver

Exceptional time management

Strong emotional intelligence

Collaborative team player

Adaptable and calm under pressure

Trusted communicator

Education

High school diploma

Additional education or certifications

Job description

With a 40+ year commitment to delivering breakthrough customer experiences, seizing initiatives, achieving results, and continuous learning, our award-winning company, Park Square Homes, has an opportunity for a talented Executive Assistant to join our team. Known for our entrepreneurial spirit, we have a strong culture rooted in trust, integrity, open communication, and respect, and we make it a point to use good judgment, fairness, and common sense to meet our challenges. Attracting top talent who can thrive in a fast-paced, entrepreneurial, family-oriented, efficient, and team-focused environment contributes to our success.

Job Overview

The Executive Assistant to the CEO serves as a strategic and operational partner to the Chief Executive Officer, enabling focus on high-impact initiatives by managing priorities, communications, and execution across business and select personal matters. This individual will anticipate needs, align stakeholders, and ensure seamless coordination across the Office of the CEO.

The role requires a polished communicator, strong critical thinker, and trusted professional who can navigate confidential matters, represent leadership appropriately, and maintain momentum when the CEO is engaged elsewhere.

Key Responsibilities

Executive & Strategic Support

• Manage the CEO’s complex calendar, priorities, and scheduling with a strong understanding of business objectives and timing sensitivities.
• Prepare agendas, briefing materials, presentations, and follow-up summaries to support executive decision‑making.
• Track key initiatives, action items, and commitments to ensure alignment, accountability, and progress.
• Draft and refine executive‑level correspondence, reports, and internal communications.
• Anticipate needs and proactively resolve issues before they escape or disrupt priorities.
• Exercise sound judgment in handling sensitive, confidential, and non‑routine matters.
• Serve as a central point of coordination between the CEO and internal/external stakeholders, ensuring timely, clear, and thoughtful communication.
• Facilitate information flow across departments, leadership, and partners.
• Collaborate closely with the Chief of Staff and other Executive Assistants to ensure continuity and cohesion within the Office of the CEO.
• Represent executive leadership with professionalism, discretion, and credibility in interactions and correspondence.

Special Projects & Business Initiatives

• Support and manage special projects aligned with organizational priorities, including research, coordination, and execution.
• Document workflows, decisions, and processes to improve efficiency and institutional knowledge.
• Provide project updates, track milestones, and follow up with stakeholders to ensure completion.
• Assist with internal initiatives related to operations, culture, and executive communications.

Event & Executive Engagement Planning

• Plan and execute executive‑level meetings, board meetings, retreats, and company‑wide events.
• Coordinate logistics, vendors, budgets, and timelines to deliver polished and well‑organized experiences.
• Oversee internal office events, leadership meetings, and special gatherings with attention to detail and brand alignment.
• Manage catering and meeting logistics, accommodating preferences and requirements as needed.
• Maintain highly organized systems for documents, contacts, records, and executive files (digital and physical).
• Coordinate complex travel arrangements and prepare expense reporting.
• Serve as a backup to other executive support functions as needed.
• Support office operations, executive visitors, and leadership meetings.

Family Office & Personal Support

• Provide limited support related to family office and foundation activities, including coordination, documentation, and scheduling.
• Assist with select personal matters and errands in a professional, discreet, and efficient manner.

Escalations & Executive Care

• Assist in managing escalated internal or external matters with professionalism and empathy.
• Support leadership in resolving time‑sensitive or high‑impact issues effectively.

Required Qualifications

• High school diploma required; additional education or certifications preferred.
• Minimum of 3–5 years of experience supporting senior executives or leadership teams.
• Experience in fast‑paced, entrepreneurial, or growth‑oriented environments strongly preferred.
• Prior experience in real estate, homebuilding, construction, or related industries is a plus.

Skills

• Proactive problem‑solver who anticipates needs, takes initiative, and exercises sound judgment.
• Exceptional time management and organizational skills with the ability to prioritize and meet deadlines.
• Strong emotional intelligence, professionalism, and executive presence; able to interact effectively at all levels.
• Collaborative team player who can also work independently in a fast‑paced environment.
• Adaptable, creative, and calm under pressure, particularly when managing events or solving problems.
• Trusted communicator with the ability to engage internal teams, external partners, and the public with discretion.

Physical Requirements

• Ability to sit, stand, and walk for extended periods as needed.
• Capability to lift and carry office supplies or packages weighing up to 25 lbs.
• Frequent use of a computer and other office equipment such as phones, copiers, and printers.