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Job Title: Executive & Personal Assistant to Two CEOs

 

About the Company:

Our client is a family-run group of businesses spanning HR outsourcing, IT hardware distribution, software development, aviation, and investments. The principals are a husband-and-wife team who each manage several companies and travel internationally for extended periods throughout the year.

 

Job Description:

Our client is hiring a sharp, discreet, highly organized Executive & Personal Assistant to support both principals across their professional and personal lives. This is a true right-hand role: you'll manage their calendars, inboxes, and travel; act as the gatekeeper who decides what information reaches them; and handle the personal and household logistics that keep their lives running smoothly. The right person treats discretion as non-negotiable, anticipates needs before being asked, and takes genuine pride in owning problems end to end.

 

Responsibilities of the role:

• Manage personal and work email across multiple accounts (Gmail, Outlook/Office 365) for both principals

• Triage and filter aggressively — surface only what truly needs their attention, handle or route the rest

• Draft responses for review and approval before anything is sent on their behalf

• Answer inbound phone calls for the principals, screen callers, and manage follow-ups

• Maintain confidentiality around sensitive business, financial, and personal matters at all times

• Own both principals' personal and professional calendars (Google Calendar, Outlook)

• Coordinate meetings across multiple companies, teams, and time zones — the principals are frequently in Europe or elsewhere abroad

• Protect their time: build in buffers, resolve conflicts, and confirm logistics so nothing falls through the cracks

• Plan and book complex domestic and international travel: flights, hotels, ground transport, and month-long stays abroad

• Book award travel using points and miles — Amex Membership Rewards, Capital One, and airline programs — using tools like Seats.aero and AwardTool

• Track points balances, elite statuses, and card benefits across programs and recommend the best redemption for each trip

• Coordinate group travel: multi-family trips, large vacation-rental bookings, group flights, and cruise/charter events (WeTravel)

• Manage long-stay logistics: furnished apartments, local services, and everything needed to set up a temporary home base abroad

• Handle disruptions in real time — rebook cancelled flights, resolve hotel issues, and adjust plans without being asked

• Book restaurant reservations, appointments, events, and experiences

• Manage household staff and service providers: housekeeper, private chef / meal prep, and other recurring help

• Source and vet solutions on demand — handyman, electrician, plumber, dry cleaning, car dealer or service, and whatever else comes up

• Coordinate gifts, celebrations, and personal errands

• Keep a running record of trusted vendors, preferences, and household details so quality stays consistent

• Work alongside the principals' existing team (executive assistant, operations, IT, and creative staff) via Microsoft Teams

• Keep tasks and follow-ups organized in HighLevel CRM and shared tools

• When presenting decisions, offer 2–3 well-researched options with clear tradeoffs and a recommendation

• Document repeatable processes so routine tasks become systems, not one-offs

 

Required Experience and Qualifications:

• 3+ years supporting executives, business owners, or high-net-worth families as an EA, PA, or estate/household manager

• Travel booking experience — travel agent background or heavy hands-on experience arranging complex international travel

• Points-and-miles fluency: you've actually booked award travel and know your way around transfer partners and award search tools (or can prove you'll learn fast)

• Excellent written and spoken English — you'll be drafting emails and answering calls as the principals' front line

• Exceptional discretion and judgment; comfortable signing an NDA and handling confidential information

• Proactive problem-solver who finds answers independently and only escalates what truly requires the principals

• Highly organized, detail-obsessed, and comfortable juggling priorities for two busy people across multiple companies

• Reliable availability during U.S. Eastern business hours with dependable internet and a quiet work setup

• Comfortable with the full toolset: Gmail, Google Calendar, Office 365, Outlook, Microsoft Teams, HighLevel CRM, airline booking sites, Amex and Capital One portals, Seats.aero, AwardTool, and WeTravel (or able to ramp quickly)

 

Preferred Skills:

• Canva or other creative/design skills (not required — we have creative staff)

• Project management experience or certification

• Experience with AI tools and workflow automation — the principals run an AI-forward operation and you'd work alongside these systems daily

• Prior experience in a family office or supporting principals who travel internationally for extended stretches

• Familiarity with luxury travel, fine dining, and premium loyalty programs

 

Personality:

• Discreet and highly organized

• Proactive problem-solver

• Detail-obsessed

• Takes genuine pride in owning problems end to end

 

Software & Tools:

• Gmail

• Google Calendar

• Office 365

• Outlook

• Microsoft Teams

• HighLevel CRM

• Airline booking sites

• Amex and Capital One portals

• Seats.aero

• AwardTool

• WeTravel

 

Schedule:

Full-time

Fixed U.S. business hours (Eastern Time)

 

Salary and Benefits:

• Payment in USD or Local Currency according to candidate's preference.

• Full-time remote opportunity.