CHERRY ASSISTANT JOBS

Executive Assistant

Remote role for Cherry Assistant through Cherry Assistant.

PART TIMEAmericas (North, Central, South America)10 hrs/weekR3,000 - R4,500 per month

Job Description

What this role covers

We are hiring an Executive Assistant to support a fast-paced entrepreneur and property portfolio owner with financial operations, Airbnb management, bookkeeping, administrative coordination, vendor research, and complex case follow-up tasks. This is a fully remote role focused on maintaining operational organization, reconciling financial information, coordinating ongoing projects, and handling sensitive administrative matters with accuracy and discretion.

The ideal candidate is highly organized, detail-oriented, resourceful, and capable of managing multiple ongoing responsibilities independently. This role requires strong communication skills, comfort working with financial systems and online platforms, and the ability to proactively follow up on unresolved issues across agencies, vendors, healthcare systems, and service providers.

Key Responsibilities

Operations & Administrative Support:

  • Provide executive and operational support across multiple ongoing projects and business activities.

  • Manage and track action items, deadlines, follow-ups, and deliverables across financial, administrative, and operational tasks.

  • Coordinate communications with government agencies, customer support departments, healthcare systems, legal service providers, and vendors.

  • Maintain detailed records of calls, case numbers, submissions, and ongoing issue resolution updates.

  • Organize and maintain digital documentation across shared systems and cloud-based platforms.

  • Conduct online research and compile organized reports, summaries, and recommendations.

  • Assist with account management, refund requests, dispute resolution, and escalation follow-ups.

  • Handle sensitive and confidential financial and personal information professionally and securely.

  • Participate in team meetings and provide progress updates on assigned tasks.

  • Support ad-hoc administrative and operational requests as needed.

Bookkeeping & Financial Operations:

  • Reconcile rental income across Airbnb, QuickBooks, bank statements, and internal financial tracking systems.

  • Pull and organize Airbnb income reports and compare payouts against recorded revenue.

  • Cross-check financial transactions and identify missing payments, discrepancies, or inconsistencies.

  • Maintain updated property pro-formas and utility tracking reports.

  • Assist with preparing organized monthly financial reporting documentation.

  • Support bookkeeping and financial organization for multiple rental properties and entities.

  • Maintain accurate financial records and organized documentation for operational use.

  • Assist with financial research, account verification, and transaction tracking.

Property Management & Airbnb Support:

  • Support Airbnb account oversight and rental income tracking.

  • Assist with Airbnb refund disputes and reimbursement follow-ups.

  • Coordinate information gathering related to property issues, booking concerns, and guest disputes.

  • Research and organize vendor options for property improvements and security solutions.

  • Assist with property-management workflow organization and operational tracking.

  • Help streamline communication, booking oversight, and expense management processes.

Research, Compliance & Case Coordination:

  • Assist with business verification, closure follow-ups, and administrative compliance tasks.

  • Coordinate documentation and follow-up related to tax filings, business registrations, and account disputes.

  • Support communications with tax agencies, healthcare providers, insurance companies, and customer support teams.

  • Track unresolved cases and escalate issues when necessary.

  • Organize supporting documentation related to claims, disputes, medical records requests, and financial matters.

  • Research vendor pricing, service comparisons, and operational solutions.

  • Maintain detailed case notes and status updates for leadership review.

Required Qualifications:

  • 3+ years of experience in executive assistance, bookkeeping, operations support, administrative coordination, or similar roles.

  • Strong experience with QuickBooks and financial reconciliation processes.

  • Excellent organizational and multitasking abilities.

  • Strong proficiency in Excel or Google Sheets.

  • Ability to manage multiple ongoing projects independently.

  • Strong written and verbal communication skills.

  • High attention to detail and accuracy.

  • Comfortable handling confidential and sensitive information.

  • Strong research and problem-solving skills.

  • Ability to work effectively in a fully remote environment.

Preferred Qualifications:

  • Experience supporting Airbnb or property management operations.

  • Experience handling financial reconciliation and reporting.

  • Familiarity with U.S.-based administrative and operational processes.

  • Experience coordinating vendor research and operational projects.

  • Familiarity with project management and collaboration tools.

  • Experience supporting entrepreneurs, executives, or small business operations.

Required Skills & Tools:

  • QuickBooks

  • Google Workspace (Docs, Sheets, Drive, Gmail)

  • Excel / Google Sheets

  • Airbnb platform familiarity

  • Financial reconciliation and reporting

  • Administrative coordination and case tracking

  • Online research and vendor comparison

  • Strong communication and organizational skills

Schedule & Pay:

  • Part-time position; U.S.-business hours in the Pacific Time Zone

  • This is a fully remote job for a U.S.-based company

  • Pay ranges from R3,000 - R4,500 per month

  • Annual raises, bonuses, confirmed holidays, and PTO.

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:

  • Competitive pay

  • Fully remote work environment

  • Diverse and engaging responsibilities

  • Opportunity to work closely with leadership

  • Exposure to financial operations, property management, and executive support

  • Long-term remote opportunity with growth potential

  • Flexible and fast-paced work environment

If you are highly organized, detail-oriented, and capable of managing financial and administrative operations with professionalism and accuracy, apply to join the team!