Demo

Offshore Executive Assistant

Heirloom
Boston, MA Contractor
POSTED ON 4/10/2025
AVAILABLE BEFORE 5/9/2025
Description

About Heirloom

Heirloom is a leading provider of large-format, luxury short-term rentals on the national level. Our unique focus on providing word-class accommodations to discerning groups of travelers in premier travel destinations, combined with a tech-enabled and data-driven business strategy, has allowed Heirloom to quickly carve out a unique space for itself within the highly competitive and rapidly evolving luxury vacation rental industry.

General Overview

The Executive Administrative Assistant will provide high-level executive, administrative, and developmental support to executive leadership. The Executive Administrative Assistant will anticipate needs and perform, coordinate, and oversee administrative and clerical duties (detailed in the “Essential Functions” section of this document). The ideal candidate for this role is a dynamic critical thinker with scrupulous attention to detail that thrives in a fast-paced work environment.

Essential Functions

  • Manage all scheduling activities for co-CEOs: i.e. daily electronic calendar, travel booking
  • Assist with email management for both Co-CEOs
  • Assist executive leadership with monthly expense reporting, as needed
  • Establish and manage insurance and tax schedule
  • Sort and address all incoming business mail
  • Place office supply restock orders: equipment for new employees, office supplies, consumables
  • Manage the registration, maintenance, and insurance of all company vehicles and properties
  • Assist with the preparation and execution of new property acquisition closing documents
  • Manage scheduling for recruiting: scheduling interviews, sending our follow-up correspondence, drafting offers, maintaining candidate CRM, etc.
  • Manage scheduling for bi-annual employee performance review process: review meetings, populating templates, generating follow up materials
  • Assist with onboarding and training of new employees (scheduling, gathering paperwork, etc)
  • Assists with the administration of special programs (i.e. internships, holiday party)
  • Special projects, as assigned

Requirements

  • Bachelor's degree
  • Exemplary planning, multi-tasking, and time-management skills
  • Prior administrative experience preferred
  • Proactive approach to problem solving (critical thinker)
  • Active learner: taking initiative comes naturally
  • Willing and able to become a notary
  • High degree of professionalism and judgment with the ability to maintain a high level of confidentiality
  • A background in Real Estate and Construction Management is essential or a plus
  • Strong business English communication skills are required, especially for investor interactions and memo creation.
  • Experience with CRM platforms like Asana, Expensify, and GSuite.
  • Excellent research skills.
  • Ability to handle inbound and outbound calls for team and vendor coordination.
  • Exceptional verbal and written communicator
  • Highly proficient in MS Office
  • Technologically literate: technology feels intuitive, not intimidating

Schedule & Compensation

This role is working in Eastern Standard Time Zone. Working Monday thru Friday up to 30 hours a week. This is a stipend role

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