Assistant Operations Manager

Company Overview

Vaaraway is a modern vacation rental management and marketing company built to help property owners increase bookings, improve guest communication, and grow rental revenue through a flexible, performance-driven approach. We support owners and lodging partners with professional listing strategy, dynamic pricing, multi-channel marketing, guest sales support, reservation management, and performance reporting—giving them access to a stronger sales and revenue platform while allowing local teams to maintain the personal hospitality that makes each property unique.

Working at Vaaraway means joining a growing luxury vacation rental brand where operations, hospitality, technology, sales, and guest experience come together. As we expand across exciting vacation markets, we're building smarter systems and stronger operational standards to support our properties, owners, guests, and teams.

If you have hands-on hospitality operations experience, know how to keep multiple priorities moving, and naturally take ownership when something needs attention, we'd love to meet you.

Position Summary

Vaaraway is looking for an experienced Assistant Operations Manager to help drive the day-to-day execution of our growing vacation rental operation.

This is not a traditional administrative support position. We're looking for someone who understands the pace and complexity of hospitality or property operations and can quickly become a trusted operational partner to our leadership team.

You'll work across Operations, Reservations, Revenue, Marketing, and our House Managers to keep priorities aligned, properties operating smoothly, and important issues moving toward resolution. You'll help coordinate new property launches, monitor operational workflows, maintain accountability across teams, and identify opportunities to make our systems and processes stronger.

The right person doesn't wait for a detailed list of instructions. You recognize what needs attention, determine the next step, communicate with the right people, and follow through until the issue is resolved.

What You'll Do

Drive Day-to-Day Operations

- Own and track operational priorities, projects, deadlines, and action items
- Identify issues requiring attention and proactively drive them toward resolution
- Coordinate across Operations, Reservations, Revenue, Marketing, and other departments
- Help prioritize competing operational needs in a fast-moving hospitality environment
- Follow up with team members to ensure commitments and deadlines are met
- Maintain visibility into outstanding issues and close communication loops
- Support operational reporting, metrics, and leadership priorities

Partner With House Managers

- Serve as a trusted operational resource for House Managers
- Monitor task completion, property needs, and operational consistency
- Help resolve day-to-day operational questions and challenges
- Hold appropriate follow-up and accountability around outstanding work
- Recognize when an issue can be handled independently and when leadership involvement is needed
- Communicate clearly and confidently across local and corporate teams

Coordinate New Property Onboarding

- Coordinate operational components of new property launches
- Build and manage onboarding checklists and timelines
- Work across departments to ensure launch requirements are completed
- Identify missing information, dependencies, and potential delays
- Follow up on outstanding action items
- Maintain accurate onboarding documentation
- Help ensure each property is operationally ready for a successful launch

Strengthen Systems & Processes

- Maintain operational documentation, resources, and SOPs in Notion
- Identify gaps, inefficiencies, and opportunities to improve workflows
- Help develop repeatable processes as Vaaraway grows
- Maintain dashboards, reporting, and operational documentation
- Capture decisions and action items from operational meetings and ensure appropriate follow-through
- Help create greater structure, visibility, and accountability across the organization

Manage Breezeway Workflows

- Maintain recurring operational tasks and property checklists
- Monitor overdue tasks and work orders
- Follow up on outstanding operational items
- Help ensure workflows are being used consistently across managed properties
- Identify opportunities to improve task management and operational efficiency

What We're Looking For

You know hospitality operations are rarely predictable. Priorities change, issues surface unexpectedly, and multiple properties and departments may need attention at the same time.

You're comfortable operating in that environment because you naturally:

- Take ownership without needing constant direction
- Recognize what needs attention and act on it
- Keep multiple priorities organized without losing important details
- Follow issues through to resolution rather than simply passing them along
- Communicate confidently with managers, owners, and internal teams
- Learn technology and new systems quickly
- Ask thoughtful questions and exercise sound judgment
- Create structure where processes are still developing
- Look for ways to make operations more efficient and scalable
- Follow through consistently and hold yourself accountable for results

You're the person others trust when something needs to get done—and you're energized by helping build better systems as a company grows.

Required Qualifications

- 2+ years of hands-on operations experience within vacation rentals, hospitality, property management, hotels/resorts, or a closely related lodging environment
- Demonstrated experience managing multiple operational priorities with limited day-to-day direction
- Strong organizational, prioritization, and problem-solving skills
- Excellent written and verbal communication
- Strong technology skills with the ability to quickly learn new platforms and workflows
- High attention to detail and consistent follow-through
- Ability to communicate professionally and confidently across multiple teams and levels of an organization

Preferred Qualifications

- Direct vacation rental management experience
- Experience coordinating property launches, onboarding, turnovers, maintenance, housekeeping, or other property operations
- Experience working with property owners and/or local property teams
- Experience with Breezeway, Notion, Google Workspace, Asana, Monday.com , ClickUp, or similar platforms
- Experience creating SOPs, improving workflows, or building scalable operational processes

Compensation & Benefits

Annual Salary: $55,000–$60,000

Benefits

- Comprehensive medical, dental, and vision insurance
- Life insurance
- Paid time off, including vacation and sick leave
- Workplace perks including food, coffee, and team activities
- Opportunity to grow alongside a rapidly expanding hospitality company
- Meaningful opportunity to influence operational systems, processes, and company growth

Schedule

- Tuesday–Saturday | 9:00 AM–5:00 PM
- Consistent Sundays and Mondays off
- On-site in Sarasota, Florida