Executive Support Specialist

About the Role

We are seeking an experienced and exceptional Executive & Administrative Assistant to support a dynamic CEO of a Private Security Company and Investment Property Company. This role is ideal for a highly organized, initiative-taking, and versatile individual who can effectively manage the professional and personal aspects of the CEO's life as well as some administrative functions within the Private Security company.

In this position, you will play a crucial role in streamlining daily operations, managing various administrative tasks, and expertly managing complex schedules. You will also oversee property-related responsibilities and provide support for family activities and personal matters.

The ideal candidate will have multiple years of experience executing meticulous attention to detail, be tech-savvy, and preferably possess some bookkeeping or accounting experience. You should be highly adaptable, demonstrating the ability to manage competing demands and prioritize effectively in fast-paced environments.

This is a unique opportunity to work directly with a CEO, providing comprehensive support across a wide range of business and personal matters.

If you are ready to take on a challenging role that demands excellence, we would love to hear from you. Join our team and be an integral part of ensuring the smooth operation of both the CEO's professional endeavors and personal life. Your skills and dedication will be essential to our executive's success.

Key Responsibilities:

Executive Support

• Manage the CEO's calendar, schedule meetings, and coordinate appointments.
• Prioritize emails, phone calls, paper mail, and other communications, collaborating with company leaders to respond to or otherwise appropriately manage communications on behalf of the CEO.
• Prepare, edit, and present correspondence, presentations, and other documents.
• Arrange travel, including flights, transportation, accommodations, and itineraries, ensuring all logistics are coordinated.
• Manage highly confidential and sensitive information with the utmost discretion.
• Perform general administrative duties such as processing incoming communications, filing, organizing, data entry, ensuring office supplies are stocked, and equipment is in working condition.
• Manage Accounts Receivable / Accounts Payable.
• Function as a liaison between the CEO and internal/external stakeholders.

Personal Support

• Assist with personal errands and daily tasks as requested, such as making reservations, scheduling appointments, accepting deliveries, purchasing gifts, personal correspondence, and running errands.
• Coordinate family or personal events, including travel and logistics.
• Organize and maintain personal files and documentation.

Property Management Support

• Assist with managing a portfolio of investment / rental properties, including tenant vetting, accounts receivable, accounts payable, and communications.
• Manage leasing agreements, renewals, and inquiries from potential tenants and tenants or property managers.
• Conduct regular announced and unannounced inspections of properties. Coordinate maintenance requests, contractors, and tenants.
• Manage the rental payment tracking and ensure timely rent collection.
• Prepare property-related reports and documentation for tax purposes or property performance analysis.
• Oversee property-related tasks such as organizing cleaning services, lawn care, or repairs as needed.
• Manage timely payments related to taxes, insurance, and other accounts payable.

Security Company Admin Support

• Assist office staff with day-to-day responsibilities, such as post office and mail runs, filing and scanning paperwork, office supply inventory, human resources support, errands, etc.
• Complete projects such as booking hotels, flights, reservations for meetings, events, conferences, etc.
• Assist the Executive Committee with ad hoc projects and tasks that supports the entire Security related business.

Project Management & Ad-hoc Tasks

• Assist in overseeing special projects, ensuring deadlines are met, and keeping the CEO updated on progress.
• Organize and track deadlines for projects related to business development or property management.
• Manage ad-hoc tasks and requests, demonstrating flexibility and the ability to problem-solve.

Requirements:

Key Qualifications Needed:

Education & Experience

• 5+ years' experience in executive support, administrative management, or personal assistant roles.
• Experience handling Accounts Receivable / Accounts Payable, bookkeeping, or general finance tasks.
• Background in property management or real estate support preferred.
• Prior experience supporting C-level leadership or entrepreneurs with diverse business interests.

Skills & Competencies

• Organization & Time Management: Exceptional ability to manage calendars, coordinate schedules, and prioritize tasks across multiple areas.
• Communication: Excellent written and verbal communication; ability to draft correspondence, presentations, and reports professionally.
• Confidentiality: Proven discretion with highly sensitive and confidential information.
• Technology: Proficiency with Microsoft Office Suite (Word, Excel, Outlook, PowerPoint) and comfort with cloud-based tools (Google Workspace, project management tools like Asana/Trello).
• Financial Skills: Competence in basic accounting, expense tracking, and payment processing. QuickBooks or similar software a plus.
• Problem-Solving: Ability to adapt quickly, anticipate needs, and resolve issues independently.
• Customer Service & Liaison Skills: Skilled at interacting with executives, vendors, tenants, and team members with professionalism and tact.

Personal Qualities

• Highly detail-oriented and proactive.
• Flexible and able to juggle changing priorities.
• Comfortable supporting both professional and personal aspects of a leader's life.
• Trustworthy, dependable, and resourceful.
• Strong follow-through and accountability on tasks big and small.

What we Offer:

• Paid Time Off (PTO): Time to rest, recharge, and take care of life outside of work.
• Competitive Compensation & Benefits: Fair pay paired with health benefits to support you and your family.
• Flexibility: We understand life happens, and we value work-life balance.
• Team Celebrations: From company outings to our annual Christmas party, we love to celebrate wins and enjoy time together.
• Positive Culture: A supportive environment where every team member matters and has a voice.

We are an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.