Operations & Systems Assistant – Breezeway & HubSpot

• Assist with setting up task automation and operational triggers where supported.

• Standardize task names, categories, and descriptions.

• Review how tasks are created, assigned, monitored, and completed.

• Identify missing checklists, duplicated tasks, and inefficient workflows.

• Help improve quality control and inspection procedures.

• Test configurations before implementation.

• Document procedures so the internal Operations team can maintain the system independently.

Goal: Create a clean, scalable Breezeway environment that allows our Operations team to manage hundreds of furnished apartments efficiently and consistently.

2. HubSpot – Internal Knowledge Base Management

Maintain and improve our internal HubSpot Knowledge Base and operational documentation.

• Create, edit, and organize Knowledge Base articles.

• Structure content into logical categories and sections.

• Format operational procedures into clear, easy-to-follow instructions.

• Convert existing documentation into standardized SOPs.

• Review existing articles for outdated or duplicated information.

• Improve article titles, organization, readability, and consistency.

• Maintain documentation for operational processes, guest services, housekeeping, maintenance, and other departments.

• Help ensure internal teams can quickly find accurate information.

• Coordinate with department managers to obtain missing or updated procedures.

• Maintain a consistent documentation structure across the organization.

Goal: Build an organized, reliable, and searchable knowledge base that employees can use to resolve operational questions and follow company procedures.

3. General Systems and Administrative Support

• Organize operational data and documentation.

• Follow implementation instructions and project priorities.

• Track assigned tasks, deadlines, and deliverables.

• Provide weekly progress updates.

• Identify problems and recommend practical improvements.

• Perform quality checks before marking work as completed.

• Coordinate with Operations and Management teams.

• Support additional software configuration and administrative projects when needed.

Required Qualifications

• Proven hands-on experience with Breezeway, preferably in vacation rentals or property management.

• Experience with HubSpot or another knowledge management or documentation platform.

• Understanding of housekeeping, maintenance, inspections, and property operations.

• Experience creating operational checklists, workflows, and standard operating procedures (SOPs).

• Excellent attention to detail and organizational skills.

• Strong problem-solving abilities.

• Excellent written English.

• Ability to work independently and follow detailed instructions.

• Comfortable with remote collaboration and task management tools.

Preferred Qualifications

• Previous experience with a vacation rental management company.

• Familiarity with Guesty, Hostaway, or similar property management systems.

• Experience configuring task automation and recurring operational workflows.

• Experience organizing operational systems for companies managing 50 or more properties.

• Familiarity with HubSpot CRM, Basecamp, and Google Workspace.

• Experience supporting distributed housekeeping and maintenance teams.

What Success Looks Like

Within the first 30–60 days, the selected candidate is expected to:

• Review and document the existing Breezeway configuration.

• Identify organizational issues and opportunities for improvement.

• Create or improve standardized housekeeping, inspection, and maintenance checklists.

• Help organize and implement operational task workflows.

• Review the structure of the HubSpot Knowledge Base.

• Begin cleaning, updating, and organizing existing articles.

• Establish a simple system for tracking completed work and outstanding improvements.

Important: We are specifically looking for candidates with practical operational software experience, not general virtual assistants whose experience is limited to data entry.

We value reliability, accuracy, initiative, and the ability to improve existing systems rather than simply follow instructions.

Originally posted on Himalayas

• Operations Assistant
• Operations Coordinator
• Systems Administrator
• Administrative Assistant

Source: Himalayas