IMPORTANT: Candidates must have prior professional vacation rental management experience. Experience as a self-host, Airbnb host, or individual property owner/operator does not qualify. Applicants must have worked in an operations role for a professional vacation rental management company overseeing a portfolio of 100+ vacation rental properties.
Company Overview
Host & Keep is a premier vacation-rental property management firm focused on delivering consistent 5-star experiences to owners and guests. We combine hospitality, operational rigor, and field execution (cleaning, maintenance, inspections) with modern systems and automation to protect owner revenue and scale operations efficiently.
Role Summary
We are seeking an experienced and highly organized Operations Manager to oversee the administrative, operational, and business support functions of our vacation rental management company. This is a high-impact leadership role responsible for ensuring operational excellence across the organization while supporting continued growth, owner satisfaction, and team performance.
This hybrid position is primarily office-based (4 days per week) and includes one day per week in the field, meeting with prospective and existing property owners, touring properties, supporting onboarding initiatives, and assisting with business development efforts as needed. While this role partners closely with the sales function, its primary focus is leading the company's administrative and operational infrastructure.
The Operations Manager serves as a key leader within the organization, overseeing booking operations, guest services, owner relations, listing management, operational reporting, escalations, and overall business efficiency. This individual will manage and support the Guest Services team, ensuring exceptional responsiveness across communication channels, booking platforms, and the guest journey.
Working closely with the Field Operations Manager, this role helps coordinate cross-functional efforts related to housekeeping, maintenance, property readiness, guest recovery, and owner satisfaction. Additional responsibilities include listing optimization, review management, owner expense tracking, insurance claim coordination, licensing and regulatory compliance, process documentation, training resources, and continuous improvement initiatives.
The ideal candidate is a strong operator who combines strategic thinking with hands-on execution, thrives in a fast-paced environment, and has a proven track record of building systems, improving processes, and leading teams.
This position offers a clear growth path to Chief Operating Officer (COO) for the right candidate who demonstrates exceptional leadership, operational excellence, and a commitment to driving the long-term success of the organization.
Key ResponsibilitiesGuest Experience & Reservations
- Manage the Guest Services team that works the inbox communication to guests.Handle guest messages as needed during the day shift, manage the company phone line, whatsapp and texts.
- Champion reservations processes across Airbnb, VRBO, direct bookings, and other channels; improve lead→book conversion and reduce time-to-book.
- Phone-first de-escalation for upset guests, coordinate vendor or field responses, and manage guest remediation to protect ratings.
- Manage review responses and reputation initiatives to maintain target listing rating (company goal: 4.8+).
- Oversee guest registration, security requirements, check-ins, and concierge services.
Team Leadership & Training
- Lead, train, and coach the Guest Services team; conduct regular tune-ups, performance reviews, and shift audits.
- Oversee the day, night & weekend GSS coverage: ensure clean handoffs, EOD reporting, and escalation protocols.
- Develop and maintain SOPs and training materials
Property Operations & Onboarding
- Coordinate property onboarding/offboarding: desktop setup, listing creation, and local walkthroughs via field teams.
- Maintain and audit SOPs and Breezeway checklists for inspections, turns, and compliance.
- Work with Field Ops and Housekeeping to schedule and triage maintenance, last-minute adjustments, and quality control.
- Setup and maintain long term tenants - add lease agreements, create contacts and monitor monthly rental payment invoices.
- Invoice vendors as needed, ensure owners files and documents are up to date and filed away
- Coordinate property showings for tenants
- Property inspections, onboarding assistance and meeting owners onsite as needed
Sales Support
- Assist with handling sales leads from marketing efforts
- Assist with site visits for new property walkthroughs and meeting owners
- Assist with client retention strategies as the lead on owner relations
Listing Management & Optimization
- Manage listing content and optimizations: titles, descriptions, photo strategy, pricing rules, and promotions.
- Ensure listings comply with local regulations, licensing language, and marketplace policies.
Expense Management & Insurance Claims
- Track and reconcile operational and owner expenses; review invoices and drive vendor cost efficiencies.
- Manage damage and insurance claims: document incidents, coordinate vendors/adjusters, and communicate claim status to owners.
- Ensure accurate record keeping for owner statements and month-end reconciliations.
Compliance & Licensing
- Coordinate license processing tasks and reminders; escalate non-compliance risks to leadership.
Systems, Automation & Continuous Improvement
- Power-user level on Guesty (required) and Breezeway (preferred): build automations, workflows, and integrations to reduce manual work.
- Use Monday.com / Google Workspace / Slack for tasking and cross-team coordination.
Owner & Stakeholder Communication
- Serve as a point of contact for owners on operational matters; share status updates and performance summaries.
KPIs & Success Metrics
- Average listing rating (goal: ≥ 4.8)
- Revenue Targets
- GSS Response times
Required Qualifications
- Bilingual: English & Spanish (preferred).
- 3+ years of professional vacation-rental/STR experience with reservations & guest services ownership.
- Guesty experience required; Breezeway and Monday.com experience strongly preferred.
- Proven people-management experience, ideally supervising reservations, field ops, and housekeeping teams.
- Strong phone customer service, conflict resolution, and guest-recovery skills.
- Experience optimizing listings on Airbnb, VRBO, and direct booking platforms.
- Highly organized with strong administrative skills, comfortable tracking expenses, owner statements, and claims.
- Remote work discipline and ability to manage distributed teams; occasional travel to Florida markets as needed.
Working Hours & On-Call Expectations
- 9am–6pm EST Rotational on-call every other weekend for high-impact escalations.
- Flexibility for early/late calls and periodic property site visits
Pay: $80,000.00 - $90,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Health insurance
- Paid time off
- Referral program
Application Question(s):
- Do you have professional operations experience working for a vacation rental management company that managed 100 or more properties (doors)?
Education:
Experience:
- professional vacation rental: 4 years (Required)
Language:
Location:
- Miami, FL 33134 (Required)
Work Location: Hybrid remote in Miami, FL 33134
