Executive Assistant (Puerto Rico-based)

Executive Assistant (Puerto Rico-based)

Work Arrangement: Fully remote, with flexibility to handle urgent tasks outside regular working hours.

Job Type: Full-time

Salary: Up to $1,500 per month, depending on experience and qualifications

Work Schedule: 40 hours per week, Monday to Friday, 9:00 AM – 5:00 PM AST

Locations: Remote, based in Puerto Rico

About Pearl Talent:
Pearl Talent connects the top 1% of candidates worldwide with leading startups in the US and EU. These startups have collectively raised over $5 billion and are backed by companies like OpenAI, a16z, and Founders Fund. Pearl looks for highly skilled candidates who can be promoted and collaborate long-term. Many candidates are flown to the US and EU for client engagements and may even receive promotions to roles based in the US.

Why Work with Us?
The company offers an opportunity to work in a dynamic, fast-growing environment with a supportive culture that values innovation and efficiency. You'll be collaborating with top-tier professionals in the property management and tech sectors, fostering professional growth while maintaining work-life balance through flexible hours.

About the Company:
The company is a cutting-edge technology firm committed to innovating and delivering unique digital solutions that transform how businesses interact with their clients. It is focused on fostering a collaborative and inclusive work environment where creativity and agility thrive. As the company grows, it seeks a Puerto Rico-based Executive Assistant to support its executive team, ensure smooth operations, and enhance productivity by managing critical administrative, operational, and organizational tasks. The ideal candidate is a proactive problem solver who brings high energy and professionalism.

Role Overview:
The Executive Assistant will serve as the cornerstone of operational and administrative support for the company's executive team, ensuring seamless execution of daily functions, optimized workflows, and proactive support for company initiatives. This includes coordinating property listings, guest communications, and maintenance schedules. By managing these essential tasks, you enable the executive team to focus on strategic planning, business expansion, and client acquisition. Your role will be pivotal in maintaining high occupancy rates, exceptional guest experiences, and efficient property turnover, contributing to the company’s goal of increasing rental revenue by 15% in the next quarter.

Key Responsibilities:

• Executive Scheduling & Calendar Management:
• Coordinate and maintain the executives' daily, weekly, and monthly schedules, managing priorities across time zones.
• Arrange meetings with clients, investors, and internal teams, ensuring all participants are informed and agendas are set.
• Manage schedule changes and communicate updates efficiently.
• Travel & Logistics Coordination:
• Plan and coordinate travel arrangements, including flights, accommodations, and transport, with detailed itineraries.
• Monitor travel expenses and prepare reports, managing receipts and documentation for reimbursement.
• Ensure all travel-related tasks, such as reservations and visa applications, are completed.
• Communication Management:
• Act as the primary point of contact for the executive team, screening calls and managing emails.
• Prepare and edit correspondence, presentations, and reports to maintain professional communication.
• Serve as a liaison between executives and stakeholders, representing Gupper LLC.
• Operational Support & Project Management:
• Assist in tracking and managing project deadlines and deliverables using project management tools.
• Coordinate with departments to align on project milestones and maintain follow-ups.
• Oversee document management, organizing digital files systematically.
• Event Planning & Coordination:
• Plan and execute team-building events, business meetings, and client presentations.
• Handle arrangements for special events such as conferences and corporate functions.
• Financial and Document Management:
• Manage expense reporting for the executive team and coordinate vendor payments.
• Organize and store company documents while maintaining confidentiality.
• Support finance-related tasks, ensuring accurate reporting.
• Personal Assistance:
• Support executives with personal errands, booking appointments, and managing reservations.
• Assist with household and wellness-related tasks to support a balanced lifestyle.

Immediate Tasks Anticipated for Week 1:

• Familiarize with executives’ schedules, routines, and communication styles.
• Organize internal and external meetings, ensuring agendas and reminders are set.
• Set up travel arrangements for upcoming trips.
• Start managing the executive’s email inbox and drafting replies for review.
• Organize and streamline digital files for easy access.
• Participate in initial meetings with key stakeholders.

• 3-5 years of experience in a high-level executive assistant role, preferably within a tech or startup environment.
• Proven track record of handling complex schedules and international travel logistics.
• Strong proficiency in digital tools like Google Workspace, Slack, and project management software.
• Highly adaptable and able to pivot quickly in a fast-paced environment.
• Professional demeanor and discretion with sensitive information.

Characteristics of Best Hires:

• Proactive Problem Solver: Anticipates needs and addresses issues before they arise.
• Strong Communicator: Skilled in both written and verbal communication.
• Tech-Savvy: Experienced with tools to streamline scheduling and task management.
• Organized and Detail-Oriented: Manages documentation with precision.
• Flexible and Adaptable: Thrives in fast-paced environments.

Characteristics of Worst Hires:

• Unorganized or struggles with multitasking.
• Lacks discretion.
• Rigid and resistant to change.
• Requires excessive supervision.

Tools and Communication Channels Used by the Team:

• Google Workspace for email and document collaboration.
• Slack for communication.
• Asana/Trello for task management.
• Zoom for virtual meetings.
• Expensify for expense management.
• Microsoft Office Suite for presentations and reports.

Competitive Salary: Up to $1,500 per month, based on experience and skills.

Remote Work: Fully remote, work from anywhere.

Generous PTO: Ample paid time off.

Direct Mentorship: Guidance from international experts.

Learning & Development: Continuous access to growth resources.

Global Networking: Opportunities to connect with professionals globally.

Work-Life Balance: Flexible hours to support a balanced lifestyle.