Executive Assistant

Location: Remote (offshore-friendly)
Commitment: Full time with an initial 2 week trial period
Compensation: Competitive, commensurate with experience (target range $2,000–$3,500/month
depending on background and hours)
Reports to: Principal (independent board director and advisor)
About the Role
I'm a former enterprise software CEO now building a portfolio of board and advisory roles, including
chairman and board seats at publicly traded and private companies. I travel internationally on a regular
basis, and I'm looking for an experienced, highly organized virtual executive assistant to manage my
calendar, coordinate travel, support board meeting logistics, and help keep my day-to-day life running
smoothly.
Primary support hours are US Eastern Time. There will be periods around international travel when
support hours will need to shift — flexibility here is important.
This is a great fit for someone who has supported a senior executive, founder, or board member
before, is comfortable adjusting to a principal's travel schedule, and takes genuine ownership of getting
things right without needing to be micromanaged.
What You'll Do
Calendar management
Own my calendar end-to-end — scheduling and re-scheduling meetings, resolving conflicts proactively,
building in travel and buffer time, and making judgment calls about priority when requests compete.
Coordinate across multiple organizations, primarily on US Eastern Time, while adjusting smoothly
during periods of international travel.
Travel coordination
Book flights, hotels, and ground transportation for both business and personal travel, including
recurring international trips. Build realistic itineraries, have backup options ready, and handle changes
calmly when plans shift.
Board meeting logistics
Coordinate with company staff and other board members' assistants to schedule board and committee
meetings, track key dates (board calendars, earnings dates, meeting prep deadlines), and help ensure
I have what I need ahead of each meeting.
Personal and lifestyle support
Occasional personal tasks — reservations, appointments, coordinating logistics between multiple
residences, and other errands that keep life organized alongside the professional workload.
Communication
Monitor and triage incoming requests (email and/or messaging), draft routine correspondence on my
behalf, and flag anything time-sensitive immediately.
What I'm Looking For
• 3+ years of experience as an executive assistant or virtual assistant supporting a senior executive,
founder, or board-level principal
• Demonstrated experience booking complex, multi-leg international travel
• Able to provide primary support during US Eastern Time business hours, with flexibility to shift hours
temporarily during periods of international travel
• Excellent written English and proactive communication style — you flag problems before they become
problems
• Fluent with standard tools: Google Workspace or Outlook/Microsoft 365 calendar, a travel-planning
tool (e.g., TripIt), and willingness to learn whatever expense/scheduling tools I use
• Discreet and trustworthy with confidential and board-level information
• Based in a time zone with workable overlap with US Eastern Time preferred, but not required for the
right candidate
Nice to Have
• Prior experience supporting a board member, C-suite executive, or someone with multiple concurrent
professional affiliations
• Experience coordinating support around a principal's international travel schedule
• Familiarity with expense management tools (e.g., Expensify, Ramp)
How We'll Work Together
I'd like to start with a short paid trial period involving real tasks — scheduling and one live travel
booking — before committing to an ongoing arrangement. From there, we can settle into a regular
rhythm of a daily or twice-daily check-in (async is fine) and a lightweight weekly look-ahead at the
calendar.
To Apply
Please share your resume or a summary of relevant experience, two references from executives or
principals you've supported (ideally someone with a board-level or multi-entity calendar), your available
hours and time zone, and your rate expectations