Executive Assistant & Multi-Business Operations Coordinator

We are seeking a highly organized, experienced, dependable, resourceful, and proactive Executive Assistant & Multi-Business Operations Coordinator to provide comprehensive executive, administrative, and operational support to the owner of multiple businesses based in the United States and the U.S. Virgin Islands.

Our businesses operate across behavioral health and social services, restaurants, hospitality, catering, private events, business consulting, media, entertainment, and creative ventures.

This is not a traditional Virtual Assistant position limited to answering email s, scheduling appointments, or completing basic administrative tasks.

We need someone who can serve as a reliable extension of the business owner, independently manage responsibilities, anticipate needs, coordinate activities across multiple businesses, and ensure that important tasks are completed accurately and on time.

The ideal candidate takes initiative, solves problems, communicates proactively, follows through consistently, and does not require constant reminders or supervision.

Key Responsibilities

1. Executive & Administrative Support

Manage executive calendars, appointments, meetings, schedules, and deadlines.

Monitor and organize email s, correspondence, and administrative communications.

Draft professional email s, letters, reports, presentations, and business documents.

Track outstanding requests, responses, assignments, and follow-up items.

Organize electronic files, business records, contracts, and administrative documentation.

Coordinate meetings and prepare agendas, notes, and action-item summaries.

Research business needs, gather information, and recommend practical solutions.

Assist with personal executive administrative responsibilities when appropriate.

Establish organized systems that improve efficiency and reduce the business owner's administrative workload.

2. Multi-Business Operations & Project Coordination

Coordinate administrative activities across multiple businesses and industries.

Maintain project trackers, task lists, operational calendars, and deadline reminders.

Follow up with Workers, contractors, vendors, and business partners regarding outstanding responsibilities.

Monitor progress on assigned projects and provide regular updates.

Assist with developing and implementing administrative procedures, workflows, and standard operating procedures.

Identify operational inefficiencies and recommend improvements.

Coordinate information between business departments and designated personnel.

Assist with business registrations, renewals, applications, and administrative compliance deadlines.

Support the implementation and maintenance of business management software and digital systems.

Help ensure business operations remain organized, efficient, and accountable.

3. Worker, Contractor & Payroll Administration

Coordinate Worker and contractor scheduling, availability, and administrative communications.

Collect, organize, and review timesheets, attendance records, and payroll-related documentation.

Follow up on missing timesheets, incomplete records, and outstanding payroll submissions.

Coordinate with supervisors and management to verify approved hours, schedules, and payroll adjustments.

Track payroll deadlines and ensure required information is submitted to the Bookkeeper on time.

Organize approved mileage, reimbursements, and other compensation-related documentation.

Assist with resolving Worker and contractor payroll inquiries and discrepancies.

Maintain organized Worker and contractor administrative records.

Assist with recruitment, applicant screening, interview scheduling, onboarding, orientation, and training coordination.

Track required onboarding documents, acknowledgments, and outstanding administrative requirements.

Payroll calculations, financial reconciliations, and accounting reports will primarily be handled by the Bookkeeper. Management retains final payroll approval authority.

4. Behavioral Health & Healthcare Administration

Assist with administrative coordination for behavioral health and social service programs.

Monitor service authorizations, expiration dates, billing deadlines, and outstanding administrative requirements.

Track documentation submissions, Provider notes, and missing administrative records.

Coordinate with Providers, case managers, authorized agencies, and internal personnel as directed.

Assist with preparing administrative reports, correspondence, and service-related documentation.

Maintain organized and confidential client and Provider records.

Track outstanding invoices, reimbursements, and payment follow-ups in coordination with the Bookkeeper.

Assist with Provider scheduling, availability, onboarding, and administrative compliance.

Follow up on unresolved administrative matters to help prevent delays in services or billing.

All responsibilities involving confidential healthcare information must follow applicable privacy, security, and organizational requirements. Clinical decisions and regulated approvals remain with authorized professionals.

5. Restaurant, Hospitality, Catering & Event Support

Provide administrative support for restaurant, bar, lounge, catering, and hospitality operations.

Coordinate with restaurant management, supervisors, and operational personnel.

Assist with tracking vendor communications, orders, purchasing requests, and administrative records.

Support event inquiries, private bookings, catering requests, and related follow-ups when needed.

Coordinate administrative tasks with designated event and marketing personnel.

Assist with updating menus, business information, websites, and digital platforms.

Track outstanding operational tasks and ensure appropriate follow-up.

Assist with organizing operational reports, schedules, and internal communications.

6. Business Development, Research & Special Projects

Research business opportunities, partnerships, vendors, and service providers.

Assist with preparing applications, proposals, presentations, and business correspondence.

Support administrative activities related to consulting, media, podcasting, entertainment, and creative ventures.

Coordinate deadlines and supporting documentation for ongoing business projects.

Research software, systems, and tools that can improve productivity and efficiency.

Assist with organizing customer, vendor, and business contact information.

Support other executive and operational projects as assigned.

7. Financial Administrative Coordination

Although a separate Bookkeeper will manage primary accounting responsibilities, the Executive Assistant will help ensure financial information is collected, organized, and submitted on time.

Responsibilities include:

Collecting and organizing invoices, receipts, and supporting documentation.

Tracking administrative payment deadlines and outstanding financial requests.

Following up on unpaid invoices and outstanding receivables as directed.

Coordinating with the Bookkeeper regarding missing financial records.

Assisting with vendor communications and payment-related inquiries.

Monitoring completion of assigned financial administrative tasks.

Helping maintain organized financial documentation across multiple businesses.

This position does not require independently preparing financial statements, performing bank reconciliations, or managing full-cycle bookkeeping.

Required Qualifications

Minimum 3 years of relevant executive assistance, administrative coordination, or business operations experience.

Demonstrated ability to manage multiple priorities, projects, and deadlines.

Excellent written and verbal English communication skills.

Strong organizational, time-management, and problem-solving abilities.

Experience coordinating with multiple individuals, departments, or businesses.

Proficiency with Google Workspace, Microsoft Office, email , calendars, and spreadsheets.

Comfortable learning new software, business platforms, and administrative systems.

Ability to work independently and proactively without constant supervision.

Strong attention to detail and commitment to accuracy.

Professional judgment, discretion, integrity, and confidentiality.

Reliable internet connection, computer, and remote working environment.

Availability to participate in scheduled meetings during U.S. business hours.

Preferred Qualifications

Previous experience directly supporting a CEO, business owner, or senior executive.

Experience supporting multiple businesses or departments simultaneously.

Healthcare, behavioral health, or social services administrative experience.

Restaurant, hospitality, catering, or event operations experience.

Experience coordinating Workers, contractors, recruitment, or onboarding.

Familiarity with payroll administration and timesheet coordination.

Experience with project management software, CRM platforms, and workflow automation.

Basic website administration and digital business management experience.

Experience with administrative billing, invoicing, or accounts receivable follow-up.

Schedule & Compensation

Position Type: Remote, part-time independent contractor.

Starting Rate: $3.75–$5.00 USD per hour, based on qualifications, experience, and demonstrated capabilities.

Initial Workload: Approximately 5–10 hours per week.

Schedule: Flexible, but applicants must be available for scheduled meetings, timely communication, and agreed-upon responsibilities during U.S. business hours when necessary.

Start Date: Immediate, following successful selection and onboarding.

Additional hours, responsibilities, and compensation adjustments may become available based on demonstrated performance, reliability, business growth, and operational needs.

Performance & Accountability Expectations

We are looking for someone who can genuinely reduce the administrative burden of managing multiple businesses.

The successful candidate must be able to:

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