CHERRY ASSISTANT JOBS

Senior Executive Assistant

Remote role for Cherry Assistant through Cherry Assistant.

FULL TIMEEurope, Middle East, and Africa (EMEA)40 hrs/weekR18,000 - R34,000 per month

Job Description

What this role covers

We are hiring a Senior Executive Assistant to provide comprehensive remote personal, family-office, and business support to the Chief of Staff, two principals, their family, household staff, and associated companies. Reporting directly to the Chief of Staff, this role will play an important part in ensuring the smooth day-to-day management of a busy, multi-country household and business portfolio, overseeing international travel, visa applications, property management, financial administration, relocation arrangements, and general executive support.

The ideal candidate has at least five years of experience as an Executive Assistant or Personal Assistant, preferably supporting a private family, family office, or high-net-worth household. They should have extensive experience managing complex international travel arrangements, visa and immigration processes, property administration, and personal affairs alongside business interests. The successful candidate will be highly organised, discreet, proactive, and persistent, with excellent communication skills and the ability to manage sensitive personal and financial information. They should be comfortable working independently in a remote environment, managing multiple priorities across different time zones, and remaining flexible when urgent travel or personal matters require additional support.

Key Responsibilities


Travel Management:

  • Take full responsibility for the end-to-end travel management process, from planning and booking through to travel days, disruptions, and post-trip expenses.

  • Arrange flights, hotels, trains, car hire, airport transfers, taxis, and restaurant reservations for the family, guests, and business visitors.

  • Complete online check-ins, download boarding passes, and prepare arrival and landing cards for international destinations, including Singapore, Malaysia, Indonesia, Taiwan, Tortola, and other locations.

  • Maintain accurate travel trackers, shared calendars, and travel documentation, including terminal information, baggage allowances, and time zones.

  • Track the principals' UK day counts and travel schedules for tax purposes.

  • Prepare detailed itineraries and travel option documents for visitors, including board meetings and business workshops.

  • Manage travel disruptions, including cancellations, rebooking, refunds, travel credits, lost baggage claims, and airline complaints.

Visas, Passports & Immigration

  • Research international entry requirements and visa regulations, and prepare and submit applications, including Schengen visas, UK visas, US ESTA, and electronic visas on arrival.

  • Take full ownership of visa applications for the family's nanny, from researching requirements through to securing approval.

  • Manage passport renewals and obtain supporting documentation, including police certificates, marriage certificates, apostilles, and notarised documents.

  • Arrange and monitor appointments, including fingerprinting appointments, and liaise with immigration advisers where required.

  • Support Spanish residency and golden visa processes, including applications for digital certificates.

  • Prepare letters of support and invitation letters using company letterhead.

Property & Holiday Let Management:

  • Manage holiday-let listings for the family's Ibiza villa across Airbnb, VRBO, and Booking.com, ensuring calendars are accurately synchronised through Uplisting.

  • Maintain and update property listings, including settings, pricing, discounts, brochures, and guest information.

  • Coordinate cleaners, private chefs, contractors, maintenance providers, and repairs.

  • Review and process supplier and contractor invoices.

  • Provide administrative support for UK rental properties, including tenancy documentation, deposits, council tax, and utilities.

  • Follow up on ongoing account, platform, and property ownership issues until they are fully resolved.

Finance & Administrative Support

  • Maintain expense trackers and prepare expense claims for each tax year.

  • Review and analyse bank statements, producing financial summaries such as income by source and calendar year.

  • Process approved payments and manage supplier invoices.

  • Gather, organise, and submit documentation required for bank account openings and financial compliance requests.

  • Manage subscriptions, including researching new tools, setting up accounts, and cancelling unused services.

  • Maintain accurate financial and administrative records while handling sensitive information confidentially.

Relocation & Household Support:

  • Provide administrative and organisational support for the family's relocation to Mallorca.

  • Obtain and compare quotations for international shipping, moving services, and storage.

  • Manage household administration, including school records, insurance renewals, deliveries, and gifts.

  • Coordinate with relevant service providers and household staff to ensure arrangements are completed efficiently.

Inbox, Calendar & Document Management:

  • Manage and update calendars, including appointments, travel arrangements, and recurring business and personal meetings.

  • Maintain an organised Google Drive, ensuring passports, certificates, contracts, travel documents, and other important records are correctly stored and accessible.

  • Draft professional emails, letters, and complaints for review and approval.

  • Maintain accurate records and ensure important documents and correspondence are organised and up to date.

Research & Business Support:

  • Research suppliers, services, and business options, presenting findings through clear comparison documents and spreadsheets.

  • Prepare organisational charts, corporate structure diagrams, presentations, and straightforward business reports.

  • Communicate with accountants, lawyers, and professional advisers by telephone and email, following up on requests and reporting outcomes.

  • Hold regular one-to-one meetings with the Chief of Staff and principals to review outstanding tasks, action lists, and priorities.

  • Attend daily check-ins with the Chief of Staff to receive task allocations, provide updates, and obtain necessary approvals.

  • Support communication and coordination between the principals, household staff, and internal business teams.

Required Qualifications:

  • At least five years of experience working as an Executive Assistant or Personal Assistant, ideally within a private family, family office, or high-net-worth household.

  • Proven experience managing a family's personal affairs alongside their business interests, including international travel for adults, children, and household staff, visa arrangements, property administration, and household support.

  • Strong understanding of the confidentiality, discretion, and professional personal service required when supporting a private family and their staff.

  • Extensive experience arranging international travel, including complex multi-leg itineraries and managing last-minute changes and disruptions.

  • Working knowledge of visa, passport, and international entry requirements for the UK, Schengen area, United States, and Southeast Asia.

  • Strong organisational and administrative abilities, with excellent attention to detail when managing dates, time zones, travel arrangements, and sensitive documentation.

  • Confident using Google Workspace, including Gmail, Calendar, Drive, Docs, and Sheets, with the ability to create trackers and use basic spreadsheet formulas.

  • Excellent written and verbal English communication skills.

  • Confidence communicating professionally by telephone and email with airlines, banks, government officials, suppliers, and professional advisers.

  • Ability to work independently, manage competing priorities, and take ownership of tasks through to completion.

  • Highly discreet and responsible when handling confidential personal, financial, and identity documentation.

  • Flexible approach to working hours, including occasional weekend and out-of-hours support when required.

Preferred Qualifications:

  • Previous experience working remotely, ideally supporting a principal or executive team across multiple time zones.

  • Experience managing holiday-let properties through Airbnb, VRBO, Booking.com, or channel management platforms such as Uplisting.

  • Basic bookkeeping or financial administration experience, including expense management and reviewing bank statements.

  • Familiarity with UK and Spanish administrative processes, including council tax, HMRC requirements, and residency procedures.

  • Basic knowledge of Spanish.

  • Experience supporting household relocations and coordinating international moving and storage arrangements.

  • Experience preparing business presentations, organisational charts, corporate structure diagrams, and professional documentation.

Required Skills & Tools:

  • Executive and personal assistant support.

  • Private family and family-office administration.

  • International travel planning and end-to-end travel management.

  • Complex flight, hotel, transport, and restaurant bookings.

  • Online check-ins, boarding passes, and travel documentation.

  • International visa, passport, and immigration administration.

  • Knowledge of UK, Schengen, US, and Southeast Asian entry requirements.

  • Property administration and holiday-let management.

  • Airbnb, VRBO, Booking.com, and Uplisting.

  • Financial administration, expense tracking, and invoice processing.

  • Reviewing bank statements and preparing financial summaries.

  • Supplier payments and subscription management.

  • Relocation coordination and household administration.

  • Google Workspace, including Gmail, Calendar, Drive, Docs, and Sheets.

  • Notion task management and WhatsApp communication.

  • Calendar, inbox, and document management.

  • Spreadsheet creation, trackers, and basic formulas.

  • Research, supplier comparisons, and business reporting.

  • Preparation of presentations, brochures, and organisational charts.

  • Professional written and verbal communication.

  • Confidence communicating with airlines, banks, government officials, and professional advisers.

  • Strong organisational, time-management, and prioritisation skills.

  • High levels of discretion and confidentiality.

  • Proactive problem-solving and persistence when resolving ongoing issues.

  • Ability to work independently and collaboratively across different time zones.

Schedule & Pay:

  • Full-Time position; 8 AM - 5 PM UK time Monday - Friday.

  • Fully remote role for a UK client.

  • Pay ranges from R18,000 - R34,000 per month.

  • Annual raises and confirmed holidays.

System Requirements:

  • Internet speed of at least 20 Mbps.

  • Computer with a 2.4 GHz processor or higher.

  • 8 GB of RAM or higher.

  • Windows 10 or newer, or Mac OS X 10.10 or newer.

  • HD 720p webcam.

  • Headset with a microphone.

Benefits:

  • Fully remote work from South Africa.

  • Consistent full-time schedule.

  • Work alongside internal teams dealing with international clients.

  • Work directly with the Customs Manager in an established organisation.

If you are an organised, detail-oriented, and reliable individual with excellent communication skills and a passion for administrative accuracy, join our team as an Import Coordinator and play an important role in delivering a smooth and efficient client onboarding experience!