Senior Executive Assistant

Location: This position can work onsite or hybrid from one of our offices in the US or fully remote (preferably College Park, MD or Chicago, IL).
Travel: Up to 15%
Job ID: 1991

The Role:

We are seeking a Senior Executive Assistant to serve as the trusted right hand to President/GM, responsible for scheduling, travel, expenses + ad hoc projects. The Executive to be supported travels frequently across multiple time zones with an extremely demanding calendar.

The ideal candidate is highly discreet with the ability to think proactively, and has appropriate judgment to act independently. This individual must possess polished communication skills to represent the Executive in this sophisticated ecosystem. Experience drafting and managing written discourse and aptitude for AI are strongly preferred.

Responsibilities:

Calendar and Scheduling

• Fast paced environment with changing cues. Active listening required.
• Prioritize incoming requests, protect Executive focus and personal time,
• Use discretion to resolve conflicts with minimal escalation
• Coordinate IT/AV for meetings, calls, and events with senior internal and external stakeholders
• Prepare daily and weekly briefings with agendas, attendee background, and materials

Travel Management

• Plan and book all domestic and international travel, including flights, cars and hotels
• Build detailed itineraries with confirmations, contacts, and contingency options
• Coordinate logistics across multiple residences and offices, including seasonal moves
• Manage passports, visas, Global Entry, loyalty programs, and travel preferences
• Monitor trips in real time and rebook quickly when plans change

Expense and Financial Administration

• Reconcile corporate and personal card expenses accurately and on schedule
• Prepare and submit expense reports with complete documentation and correct coding
• Track invoices, vendor payments, memberships, and subscriptions
• Maintain budgets for travel and events and flag anomalies
• Liaise with finance, accounting, or family-office teams as needed

Communications

• Manage the principal's inbox: triage, draft replies, and flag priorities
• Draft correspondence, as needed
• Act as the first point of contact, representing the principal professionally and diplomatically
• Coordinate with communications, PR, or social teams on announcements and appearances
• Maintain accurate contact lists, gift records, and relationship notes

Requirements:

• 5+ years of executive assistant experience in Tech or Finance, including at least 3 years supporting a C-suite executive, founder, or high-net-worth principal,
• Advanced proficiency in Google Workspace and/or Microsoft 365
• Proven mastery of complex calendar management across time zones
• Extensive experience booking domestic and international travel
• Strong expense management skills with tools such as Concur, Expensify, Navan, or Ramp
• Exceptional written and verbal communication skills
• Demonstrated discretion with highly confidential business and personal information
• Bachelor's degree

Preferred Qualifications:

• Strong aptitude for AI including but not limited to Claude & ChatGPT
• Experience drafting external correspondence and executive talking points
• Familiarity with travel between multi-residence logistics

Core Competencies:

• Anticipation: sees problems and needs before they surface
• Judgment: knows when to decide independently and when to escalate
• Discretion: trusted with sensitive personal, financial, and business matters
• Composure: calm and solution-focused under pressure and last-minute change
• Polish: gracious, professional presence with VIPs, staff, and vendors
• Precision: meticulous with details, numbers, and follow-through
• Flexibility: available outside standard hours when travel or urgent matters require

The total compensation package includes base, bonus, equity, and a range of benefit options found on our career site.