Executive Assistant to CEO-Support Multiple Companies

We are seeking a highly organized, tech-savvy Executive Assistant to support CEO , an entrepreneur managing several fast-growing companies in hospitality, property management, laundry services, and real estate.

This role supports the operations of multiple businesses including:

• Lakecation Vacations – Luxury vacation rental management
• Maid Squad Ozarks – Professional cleaning services
• Aloha Laundry Co. – Commercial laundry and linen services
• Property Squad – Maintenance and property services

This is a high-trust role working directly with the CEO to keep multiple businesses organized, moving, and growing.

The ideal candidate thrives in a fast-paced entrepreneurial environment, is proactive, detail-oriented, and loves systems, organization, and solving problems.

Key Responsibilities
Executive Support

• Manage CEO calendar and appointments
• Coordinate meetings, calls, and travel planning
• Organize daily priorities and task lists
• Draft email s and professional communications
• Handle confidential business information

Operations & Administrative Support

• Assist with project coordination across multiple companies
• Track tasks and deadlines across departments
• Organize digital files and documents
• Assist with hiring, onboarding, and team coordination
• Manage vendor and contractor communications

Marketing & Digital Support

• Assist with social media scheduling
• Coordinate marketing content and campaigns
• Upload listings and property content
• Assist with CRM updates and database management

Customer & Owner Support

• Assist with guest and homeowner communication when needed
• Help monitor inboxes and respond professionally
• Support customer experience and concierge requests

Technology You Will Use

Applicants should be comfortable learning and using digital tools such as:

• Google Workspace (Docs, Sheets, Calendar, Drive)
• Slack or internal communication tools
• Hostaway (property management software)
• QuickBooks
• Canva
• CRM systems
• Project management tools (Asana / ClickUp / Monday)
• Social media platforms

Experience with AI tools and automation is a plus.

Skills & Qualifications
Required Skills

• Excellent written and spoken English
• Strong organization and time management
• Ability to manage multiple priorities
• Detail-oriented and proactive
• Strong communication skills
• Comfortable learning new technology quickly
• Ability to work independently

Preferred Skills

• Executive assistant experience
• Experience working with U.S.-based companies
• Hospitality or property management experience
• Social media or marketing support experience
• CRM or automation experience

Compensation

$6.50 – $8.00 per hour depending on experience.

Opportunity for long-term growth and leadership roles as the companies expand.

What Success Looks Like

The right candidate will become a trusted right hand to the CEO, helping keep multiple companies organized, efficient, and moving forward.

This is a role for someone who enjoys building systems, solving problems, and supporting a visionary entrepreneur.