Executive Assistant to Busy CEO (Support Multiple Companies)

Full Job Description

About the Role

We are seeking a highly organized, tech-savvy Executive Assistant to support CEO Tia Blehm, 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 ResponsibilitiesExecutive Support• Manage CEO calendar and appointments

• Coordinate meetings, calls, and travel planning

• Organize daily priorities and task lists

• Draft emails 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

Job Responsibilities

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 ResponsibilitiesExecutive Support• Manage CEO calendar and appointments• Coordinate meetings, calls, and travel planning• Organize daily priorities and task lists• Draft emails and professional communications• Handle confidential business informationOperations & 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 communicationsMarketing & Digital Support• Assist with social media scheduling• Coordinate marketing content and campaigns• Upload listings and property content• Assist with CRM updates and database managementCustomer & Owner Support• Assist with guest and homeowner communication when needed• Help monitor inboxes and respond professionally• Support customer experience and concierge requestsTechnology 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 platformsExperience with AI tools and automation is a plus.Skills & QualificationsRequired 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 independentlyPreferred 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

Job Requirements

Job Requirements (English)

Excellent written and spoken English communication skills

Strong organization and time management abilities

Ability to manage multiple tasks and priorities in a fast-paced environment

Comfortable working independently in a remote position

Strong attention to detail and problem-solving skills

Experience with administrative or executive assistant support preferred

Ability to learn and work with multiple software platforms and digital tools

Reliable internet connection and quiet work environment

Strong professional communication and customer service skills

Comfortable supporting multiple businesses and teams simultaneously

Willingness to work U.S. Central Time hours

Positive attitude, proactive mindset, and strong work ethic

Skills Required

• Phone Support - Expert
• Financial Reporting - Intermediate
• Business Communication - Intermediate
• Business Administration - Expert

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