Remote, executive administrative assistant

We are seeking a highly dependable, discreet, and technologically capable individual with skills in AI, ChatGPT, and remote executive operations to support year-round business operations, administrative systems, scheduling, communication, and select owner-support responsibilities.

This role is ideal for someone who is organized, calm, trustworthy, detail-oriented, and comfortable working remotely with clear accountability. The right candidate will be able to manage tasks independently, protect confidential information, communicate professionally, and help keep important business details moving forward.

• Manage administrative tasks, scheduling, reminders, and follow-ups
• Support daily communication through Slack, email, and shared task systems
• Assist with QuickBooks tasks such as invoices, expenses, receipts, and basic reporting
• Work with Fair Harbor or similar reservation/booking software
• Organize digital files, documents, permits, contracts, insurance records, and company information
• Track projects, deadlines, renewals, open tasks, and owner priorities
• Draft professional customer, vendor, and internal communications
• Help maintain calendars, appointments, reminders, and recurring administrative routines
• Support selected confidential business and owner-related administrative tasks
• Provide regular updates so priorities, deadlines, and next steps are clear

• Strong discretion and respect for confidential business and personal information
• Proven ability to work remotely and complete tasks without constant supervision
• Strong technology skills and ability to learn new platforms quickly
• Experience with Slack, QuickBooks, Google Workspace, Microsoft Office, or similar tools
• Excellent written communication and follow-through
• Highly organized and detail-oriented
• Calm, professional, and low-drama communication style
• Ability to manage multiple priorities and keep tasks moving
• Comfortable working in a small-business environment where responsibilities may vary by season

• Experience with Fair Harbor or other reservation / booking systems
• Experience supporting an owner, executive, entrepreneur, or small-business operator
• Basic bookkeeping or financial administration experience
• Experience creating task trackers, checklists, SOPs, or organized workflows
• Background in tourism, outdoor recreation, hospitality, operations, or customer service

$48,000–$55,000 per year, depending on experience, skill level, and fit.

This is a remote, year-round position. The role requires consistent communication, reliable availability, strong task completion, and the ability to work independently.

This position involves access to sensitive company and owner information. The selected candidate must demonstrate excellent judgment and will be required to sign a confidentiality agreement.

Please submit your resume and a brief note explaining:

1. Your experience working remotely
2. The administrative systems and software you have used
3. Your experience handling confidential information
4. Why you would be a strong fit for a small-business operations support role