Executive Assistant

Job Overview The Executive Assistant provides direct support to the principal through expert calendar management, detailed travel planning, and seamless day-to-day coordination. The ideal candidate is comfortable operating in a tech-first, fast-paced, collaborative environment and brings strong judgment, discretion, and care to managing complex logistics at a high standard. Duties Calendar Management & Executive Support Own and manage the principal’s complex calendar, including scheduling meetings, resolving conflicts, and ensuring time is aligned with priorities. Coordinate internal and external meetings across multiple stakeholders and time zones. Ensure the principal’s schedule is accurate, current, and clearly communicated to relevant team members. End-to-End Travel Management Lead all phases of travel planning, including intake, research, booking, itinerary creation, in-trip support, and post-trip follow-up. Manage a pipeline of upcoming trips of varying complexity, from local Puerto Rico travel to mainland U.S. travel to multi-city international itineraries. Assess and prioritize travel-related tasks based on complexity, timing, purpose, and stakeholder involvement, including personal travel, relationship travel, and business travel. Travel Research & Booking Conduct thorough research on flights, accommodations, dining, ground transportation, activities, and wellness-related experiences. Present curated, ranked recommendations with clear rationale to support fast, informed decision-making. Book and manage all travel components using preferred platforms, vendors, and loyalty programs. Oversee seat selection, frequent flyer accounts, TSA PreCheck, check-ins, and boarding pass delivery. Itinerary Development & Stakeholder Coordination Build comprehensive, detail-rich itineraries that include daily schedules, logistics, contact information, and contingency plans. Lead pre-trip kickoff and final briefing meetings with the principal and other relevant stakeholders. Ensure plans are confirmed, calendared, and shared with the broader team when helpful for visibility and coordination. Add all trip-related events to the principal’s calendar with accurate time zones, travel buffers, and reminders. Coordinate calendar adjustments across time zones, especially for international travel. Real-Time In-Trip Support Provide responsive support during travel, including handling disruptions such as delays, cancellations, lost luggage, and urgent medical or logistical issues. Send daily itinerary updates and reminders for more complex trips. Manage timely ad hoc requests that arise while the principal is traveling. Adjust working hours as needed to support early flights, late arrivals, and time zone differences during active travel periods. Post-Trip Follow-Through & Continuous Improvement Facilitate post-trip debriefs and gather feedback from the principal. Update travel preferences, destination notes, databases, and SOPs based on lessons learned. Reconcile travel expenses and ensure receipts and documentation are uploaded accurately and promptly. Communication & Cross-Functional Collaboration Serve as a primary point of contact between the principal, leadership team, and internal or external stakeholders. Communicate with professionalism, warmth, discretion, and clarity. Provide timely, detailed updates to the team regarding schedule changes, travel plans, and other relevant principal-related logistics. Collaborate closely with the broader support team, including leading group assistant meetings with the principal when needed. Office, Event, and Administrative Support Help maintain an organized and professional office environment shared by the family office team. Support the planning and coordination of company meetings, offsites, and other executive or team events. Assist with financial and administrative tasks as needed. Provide ad hoc support to team leads and staff in a way that strengthens overall team effectiveness. Confidentiality & Judgment Handle highly sensitive information with exceptional discretion and sound judgment. Maintain the highest standards of confidentiality, professionalism, and trust in all interactions and communications. Ideal Candidate Profile: 5–7+ years of experience in an Executive Assistant, travel management, or similar high-trust support role, ideally supporting a principal, founder, or C-suite executive with complex personal and business travel. Deep experience managing complex calendars, coordinating across multiple stakeholders, and handling travel that requires precision, adaptability, and strong judgment. Strong organizational and analytical skills, with the ability to manage many moving pieces without losing attention to detail. Excellent research and decision-support skills, with the ability to synthesize options into clear, ranked recommendations. Strong written communication skills, including the ability to produce concise briefings, polished updates, and clear decision rationales. Warm, grounded, and professional verbal communicator who can build trust across a calm, low-ego, high-care team culture. Highly self-directed and proactive, with a bias toward proposing solutions rather than waiting for instructions. Comfortable operating in ambiguity and adapting to changing priorities, shifting timelines, and evolving scope. Strong sense of ownership, follow-through, and commitment to continuous improvement. Tech-savvy and systems-oriented, with comfort using tools such as Notion, Google Calendar, Ramp, project management platforms, and travel booking systems. Available full-time, with meaningful overlap with Atlantic Standard Time and willingness to provide support outside standard hours for defined travel-related needs. Bilingual in English and Spanish. General Guidelines: Always maintain a professional and positive demeanor. Communicate clearly, promptly, and professionally with principal, team members, vendors, and clients. Stay informed on office policies, procedures, and best practices. Effectively manage time to meet deadlines and proactively avoid delays. Complete assigned tasks and projects on time and to quality standards, aligned with company norms, boundaries and best practices. Actively contribute to team discussions, decision-making, and cross-functional support. Seek and offer feedback to support continuous learning and team performance. Assist with special projects and other duties as assigned. Pay: From $80,000.00 per year Benefits: Dental insurance Employee assistance program Flexible schedule Health insurance Life insurance Paid time off Parental leave Professional development assistance Tuition reimbursement Vision insurance Work Location: In person