Executive Assistant to CEO in New York, New York at STAYTERRA VACATIONS LLC

Executive Assistant to the CEO
Company: StayTerra Location: New York/ Tri state Area
Reports To: Chief Executive Officer Employment Type: Full-Time, Exempt

About StayTerra
StayTerra is a collection of premier vacation rental property management brands, united on a single platform to deliver best-in-class property management for owners and elevated, seamless experiences for guests across top destinations in America. Backed by Garnett Station Partners and Bessemer Venture Partners, StayTerra is scaling quickly through organic growth and acquisition, bringing a hospitality-first mindset to a fragmented industry.

Position Overview
StayTerra is seeking a highly organized, discreet, and proactive Executive Assistant to support the CEO in a fast-paced, high-growth environment. This role is central to the CEO's ability to operate efficiently — managing complex calendars, travel, communications, and cross-functional coordination while representing the executive office with professionalism and sound judgment. The ideal candidate anticipates needs before they're voiced, handles sensitive information with absolute discretion, and thrives on bringing order to a dynamic, fast-moving business.

Key Responsibilities:
Calendar & Time Management
• Own and manage the CEO's complex calendar, proactively resolving conflicts and prioritizing time against business-critical activities
• Coordinate scheduling across internal leadership, board members, investors, and external partners

Travel & Logistics:
• Arrange detailed domestic and occasional international travel itineraries, including flights, hotels, ground transportation, and contingency planning
• Manage travel changes in real time and troubleshoot issues as they arise
Communications & Correspondence
• Draft, proofread, and manage correspondence on behalf of the CEO, including emails, memos, and presentation materials
• Serve as a gatekeeper and liaison between the CEO and internal teams, board members, investors, and external stakeholders
• Screen and prioritize incoming communications, flagging urgent matters appropriately

Meeting & Board Support:
• Prepare agendas, briefing materials, and follow-up action items for executive, leadership, and board meetings
• Take and distribute meeting minutes as needed; track action items to completion
• Coordinate logistics for board meetings, investor updates, and offsites
Project & Office Coordination
• Support special projects and cross-functional initiatives at the direction of the

CEO:
• Coordinate with department heads (Operations, Finance, Revenue Management, HR) to gather information and track deliverables on behalf of the CEO
• Assist with expense reports, invoice processing, and budget tracking for the executive office

Confidentiality & Judgment
• Handle highly sensitive company, personnel, and strategic information with the utmost discretion
• Exercise independent judgment in prioritizing tasks and representing the CEO's interests

Qualifications:
• 5+ years of experience as an Executive Assistant supporting a C-suite executive, ideally at a private equity backed, hospitality, real estate, or high-growth company
• Exceptional organizational skills with the ability to manage multiple priorities under tight deadlines
• Outstanding written and verbal communication skills
• High proficiency with Microsoft Office / Google Workspace and calendar/travel management tools
• Demonstrated discretion in handling confidential and sensitive information
• Comfortable operating in a fast-paced, entrepreneurial, and evolving environment
• Strong interpersonal skills with the ability to build trust across all levels of the organization
• Bachelor's degree preferred but not required with equivalent experience

Preferred Attributes
• Experience supporting an executive at a multi-brand, multi-location, or portfolio company
• Familiarity with the vacation rental, hospitality, or property management industry
• A calm, solutions-oriented demeanor under pressure
• A genuine service mindset anticipates needs and takes ownership without being asked

What StayTerra Offers
• Competitive salary commensurate with experience
• Comprehensive benefits package (medical, dental, vision, 401(k))
• The opportunity to play a pivotal role at a fast-growing, well-capitalized company in the vacation rental industry
• A collaborative, hospitality-first culture
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StayTerra is an equal opportunity employer.