Assistant Operations Manager

Assistant Operations ManagerVaaraway 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.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 directionRecognize what needs attention and act on itKeep multiple priorities organized without losing important detailsFollow issues through to resolution rather than simply passing them alongCommunicate confidently with managers, owners, and internal teamsLearn technology and new systems quicklyAsk thoughtful questions and exercise sound judgmentCreate structure where processes are still developingLook for ways to make operations more efficient and scalableFollow through consistently and hold yourself accountable for resultsYou'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 environmentAbility 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 skillsExcellent written and verbal communicationStrong technology skills with the ability to quickly learn new platforms and workflowsHigh attention to detail and consistent follow-throughAbility to communicate professionally and confidently across multiple teams and levels of an organizationPreferred Qualifications:Direct vacation rental management experienceExperience coordinating property launches, onboarding, turnovers, maintenance, housekeeping, or other property operationsExperience working with property owners and/or local property teamsExperience with Breezeway, Notion, Google Workspace, Asana, Monday.com, ClickUp, or similar platformsExperience creating SOPs, improving workflows, or building scalable operational processesCompensation & Benefits:Annual Salary: $55,000-$60,000Benefits:Comprehensive medical, dental, and vision insuranceLife insurancePaid time off, including vacation and sick leaveWorkplace perks including food, coffee, and team activitiesOpportunity to grow alongside a rapidly expanding hospitality companyMeaningful opportunity to influence operational systems, processes, and company growthSchedule:Tuesday-Saturday | 9:00 AM-5:00 PMConsistent Sundays and Mondays offOn-site in Sarasota, Florida (Not Remote or Hybrid)