View all jobs

Assistant Operations Manager

  • Sarasota, FL

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 seeking an experienced, hands-on Assistant Operations Manager to support the daily operations of our growing luxury vacation rental portfolio in Sarasota, Florida.

This is an on-site, operations-focused position, not a remote or traditional administrative support role. You'll work closely with leadership, House Managers, and cross-functional teams to keep properties running smoothly, coordinate new property launches, resolve operational challenges, and improve processes.

We're looking for someone with experience in hospitality, vacation rentals, hotels, resorts, or property management who thrives in a fast-paced environment and takes ownership without needing constant direction.

If you're organized, proactive, comfortable with technology, and enjoy solving problems while supporting a growing hospitality operation, we'd love to hear from you.

What You'll Do

Daily Operations & Team Coordination

  • Manage operational priorities, projects, deadlines, and action items to keep daily operations running smoothly.

  • Coordinate across Operations, Reservations, Revenue, Marketing, and House Managers to maintain alignment and resolve issues.

  • Monitor operational performance, follow up on outstanding commitments, and escalate concerns when appropriate.

Property Operations & House Manager Support

  • Partner with House Managers to monitor property needs, task completion, and operational consistency.

  • Help resolve day-to-day challenges involving property readiness, maintenance, housekeeping, and other operational needs.

  • Maintain clear communication and accountability across local and corporate teams.

New Property Onboarding

  • Coordinate new property launches, including onboarding checklists, timelines, documentation, and operational readiness.

  • Collaborate with departments to identify missing information, potential delays, and outstanding launch requirements.

  • Ensure action items are completed so new properties are prepared for successful launches.

Systems, Processes & Workflow Management

  • Maintain operational documentation, SOPs, resources, and reporting in Notion and other company systems.

  • Manage recurring tasks, property checklists, work orders, and overdue items in Breezeway.

  • Identify process gaps, improve workflows, and help develop scalable operational standards.

  • Maintain dashboards and reporting to provide leadership with visibility into operational priorities and performance.

  • Document decisions and action items from operational meetings, ensuring appropriate follow-through.

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

  • Ability to work on-site in Sarasota, Florida, Tuesday through Saturday, 9:00 AM–5:00 PM.

  • Experience coordinating day-to-day operations in a fast-paced, service-oriented environment.

  • 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 (Not Remote or Hybrid)