Executive Assistant & Office Mgr

Park Square Homes•Orlando, FL

1d•Onsite

About The Position

Executive Assistant to CEO & Office Manager 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 & Office Manager 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 & Office Manager at Park Square Homes serves as a trusted operational and strategic partner to the CEO and COO, enabling both executives to focus on high-impact priorities by managing their schedules, communications, and administrative needs with precision and discretion. Beyond executive support, this role owns the day-to-day management of the corporate office environment and partners with the existing Executive Assistant on company-wide and internal events. This individual will also provide select personal support to the CEO and COO as needed. This is a high-trust, high-visibility role that requires exceptional judgment, professionalism, organizational mastery, and the poise to represent executive leadership at every level of the organization.

Requirements

Minimum of 5+ years of executive assistant experience supporting C-suite or senior leadership, ideally with dual-executive or multi-principal support experience.
Demonstrated experience managing office operations, facilities, or an office management function.
Experience planning and executing corporate events, executive retreats, or company-wide gatherings from concept through completion.
Comfort with select personal and family office support in a professional and discreet capacity.
Proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint) and calendar/collaboration tools required.
High school diploma required

Nice To Haves

Experience in a fast-paced, entrepreneurial, or growth-oriented environment strongly preferred; homebuilding, real estate, or construction background a plus.
Bachelor's degree or additional certifications in office administration, business, or a related field preferred.
Executive presence and professional poise — the ability to represent the CEO and COO with confidence, credibility, and professionalism in any setting, whether fielding a stakeholder call, managing a board meeting, or greeting a guest at the front desk.
Exceptional judgment and discretion — the kind of trusted, instinctive judgment that allows this individual to handle sensitive information, personal matters, and confidential situations without instruction, and without error.
Organizational mastery — the ability to manage two executive schedules, a full office operation, event logistics, and special projects simultaneously without losing accuracy, missing a deadline, or letting anything fall through.
Proactive anticipation — consistently one step ahead of both executives' needs, identifying issues before they arise and resolving them before they disrupt priorities or require escalation.
Adaptability and composure under pressure — stays calm, focused, and effective when priorities shift rapidly, timelines compress, or unexpected challenges arise in either the executive support or office management functions.
Collaborative partnership — works closely and effectively with the existing Executive Assistant and department leaders, contributing to a cohesive, high-functioning executive support team.
Service orientation — genuinely invested in making the CEO, COO, and the entire office team more effective and well-supported, taking pride in every detail and viewing no task as beneath the role.
Clear and polished communication — produces executive-quality written correspondence, communicates with confidence across all levels of the organization, and exercises appropriate judgment about what to say, how to say it, and when.

Responsibilities

Manage the complex, high-volume calendars of both the CEO and COO with a strong command of their priorities, time sensitivities, and business objectives — proactively resolving conflicts and ensuring each executive is set up for every commitment.
Prepare agendas, briefing documents, presentations, and follow-up summaries that support informed executive decision-making and keep key initiatives moving forward.
Track commitments, action items, and deadlines across both executives' workstreams, ensuring nothing falls through and that accountability is maintained across all stakeholders.
Draft and refine executive-level correspondence, internal communications, memos, and reports on behalf of the CEO and COO with accuracy, professionalism, and appropriate voice.
Arrange complex domestic and international travel itineraries, accommodations, ground transportation, and detailed travel briefings; manage expense reporting promptly and accurately.
Anticipate needs and proactively resolve potential issues before they escalate, serving as a stabilizing and enabling force within the Office of the CEO and COO.
Exercise sound judgment in handling sensitive, confidential, and time-critical matters on behalf of both executives.
Collaborate closely with the existing Executive Assistant and Chief of Staff to ensure continuity, cohesion, and seamless support within the executive function.
Own the day-to-day operations of the corporate office environment, ensuring the space is clean, well-organized, fully stocked, and consistently reflective of the Park Square Homes brand and culture.
Serve as the primary point of contact for visitors, vendors, and guests at the corporate office, providing a professional, welcoming, and brand-aligned experience at all times.
Manage office vendor relationships including facilities, supplies, equipment, maintenance, and building management — ensuring service levels are met and costs are controlled.
Maintain organizational systems for office records, documents, contact databases, and filing — both digital and physical — ensuring information is accessible, current, and secure.
Oversee office supply inventory, ordering, and distribution; manage incoming and outgoing mail, deliveries, and document handling.
Coordinate office logistics related to seating arrangements, workspace needs, renovations, and facilities-related requests.
Process and organize office expense reports, credit card statements, and vendor invoices; escalate any financial discrepancies appropriately.
Act as a resource for team members with office-related needs, questions, or issues, maintaining a productive and well-supported work environment.
Partner with the existing Executive Assistant to plan, coordinate, and execute company-wide internal events including employee recognition events, holiday gatherings, town halls, department celebrations, and culture initiatives.
Manage all event logistics from concept through execution: venue coordination, catering, vendor management, guest communications, setup, and post-event follow-up.
Plan and execute executive-level meetings, board meetings, leadership retreats, and special gatherings with meticulous attention to detail, timeline management, and a polished outcome.
Order and coordinate catering for executive meetings and company events, accommodating dietary preferences and restrictions and ensuring all details are handled in advance.
Manage event budgets and vendor relationships in partnership with the executive team, ensuring events are delivered on time and within budget.
Provide select personal support to the CEO and COO as needed, including scheduling personal appointments, managing personal errands, and handling time-sensitive personal logistics with the highest level of discretion.
Assist with family office coordination and personal matters in a professional, confidential, and efficient manner, adapting to evolving needs with flexibility and good judgment.
Run personal and corporate errands as required, managing priorities and logistics effectively across both professional and personal requests.
Serve as a professional and credible point of coordination between the CEO, COO, and internal or external stakeholders — ensuring communication is timely, clear, and handled with appropriate discretion.
Facilitate information flow across departments and leadership, following up on action items and ensuring key parties are informed and aligned.
Represent executive leadership with professionalism and poise in all correspondence and interactions, including with board members, investors, clients, and external partners.
Handle escalated internal or external matters on behalf of the CEO and COO with sound judgment, empathy, and urgency, resolving issues effectively and keeping leadership informed.
Support and independently manage special projects aligned with executive and organizational priorities, including research, coordination, stakeholder communication, and execution.
Document workflows, decisions, and processes to improve institutional knowledge and operational efficiency.
Provide regular project updates, track milestones, and follow up with stakeholders to ensure completion and accountability.