Operations & Systems Assistant – Breezeway & HubSpot

Operations & Systems Assistant – Breezeway & HubSpot

Department: Operations Job Type: Part-Time Freelancer Work Arrangement: Remote Hours: Up to 20 hours per week Location: Remote, worldwide.

Schedule: Flexible working hours, with availability for scheduled team meetings.

About Corporate Stays

Corporate Stays is an international furnished apartment rental and property management company operating across Canada and Latin America.

We manage a growing portfolio of furnished apartments and rely on operational platforms to coordinate property management, housekeeping, maintenance, guest services, and internal procedures.

We are looking for an experienced Operations & Systems Assistant to help us organize, configure, and optimize two important platforms: Breezeway and HubSpot Knowledge Base .

This is not a traditional virtual assistant position. We need someone comfortable working directly with operational software, building structured workflows, organizing information, and improving processes.

Key Responsibilities

1. Breezeway – Property Operations Management

Our main priority is to properly configure, organize, and optimize Breezeway for our property management operations.

• Review and organize the existing Breezeway setup.
• Create and improve housekeeping, inspection, and maintenance task templates.
• Develop standardized operational checklists for different property types.
• Organize property-specific instructions, notes, and operational information.
• Help configure recurring tasks and operational schedules.
• Review task assignments, priorities, and workflows.
• 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.