Executive Assistant

COMPANY OVERVIEW:

Awayday is the leading vacation rental management company in the United States, managing over 7,000 vacation rentals across premier resort locations, growing rapidly and gaining market share. We are committed to delivering exceptional service to property owners and unforgettable experiences to guests, as well as innovating the industry model to focus on local operations turbocharged by industry-leading operating practices and a relentless learning culture.

At Awayday, we are driven by a mission to Perfect the Vacation Rental Experience.  Our Core Values are our guiding principles: Servant Leadership, Ownership, Mentality, Local, and Excellence. We are looking for a Chief Operating Officer who shares these values and is ready to lead by example.

POSITION SUMMARY:

We are seeking a highly organized, resourceful, and proactive professional who thrives in a fast-paced environment where attention to detail and a winning mindset make all the difference. This Executive Assistant isn’t just a support role—they are a critical force behind the success of the executive team, ensuring seamless operations, precise execution, and proactive problem-solving while keeping high-priority projects on track and ensuring deadlines and deliverables are met.

The ideal candidate anticipates needs, takes ownership, and stays two steps ahead. They don’t just manage schedules and book travel—they create efficiency and alignment, working cross-functionally with department heads to ensure initiatives stay on course. They conduct research and compile key information to support executive decision-making and ensure leadership has the resources and insights needed to operate effectively.

This person is high-energy, efficient, and relentlessly reliable, stepping in wherever needed to ensure nothing falls through the cracks. They maintain organized records, files, and key documents, ensuring seamless access to critical information. Additionally, they coordinate special projects and strategic initiatives, ensuring timely execution and follow-through. In a high-growth environment like Awayday, they understand that speed, precision, and discretion are equally vital.

They are passionate about ownership, accountability, and execution, knowing that success is built on discipline and smart problem-solving. Adaptable and strategic, they bring order to chaos, troubleshoot before issues arise, and make the executive team more effective every day.

RESPONSIBILITIES:

• Manage complex calendars, schedule meetings, and coordinate travel arrangements for Executive Team members.
• Handle confidential and time-sensitive information with discretion and professionalism.
• Prepare reports, presentations, and executive summaries as needed.
• Screen and manage emails, phone calls, and correspondence on behalf of executives.
• Coordinate and book extensive domestic and international travel, ensuring seamless itineraries.
• Manage transportation, accommodations, and meeting logistics for executives attending conferences, board meetings, and site visits.
• Plan and execute executive meetings, including preparing agendas, taking detailed notes, and following up on action items.
• Act as a liaison between executives and internal/external stakeholders, ensuring smooth communication and collaboration.
• Assist in organizing quarterly leadership meetings, board meetings, and offsite events.

QUALIFICATIONS:

• 5+ years of experience as an executive assistant or in a similar high-level administrative role.
• Experience supporting C-suite executives or senior leadership in a fast-paced environment.
• Proficiency in Microsoft Office Suite and project management tools.
• Strong background in travel coordination, event planning, and calendar management.
• Prior experience in hospitality, real estate, or vacation rental management is a plus but not required.

COMPENSATION & BENEFITS:

Annual Salary: $70,000 - $80,000

Benefits

• Health insurance
• Dental insurance
• Vision insurance
• Retirement benefits or accounts
• Long term disability insurance
• Short term disability insurance

Schedule

• Monday - Friday