Reservation Specialist

Reservation Specialist
Hollywood, FL | On-Site | $40-45,000 + commission

StaySouth Vacation Homes is a locally owned vacation rental management company serving Miami-Dade, Broward, and Palm Beach counties. As part of the Casago network, we combine professional hospitality management, advanced technology, and local expertise to provide exceptional service to guests and homeowners.

As we grow our portfolio, we are seeking a Reservation Specialist who can manage incoming booking opportunities, convert qualified inquiries into confirmed reservations, and ensure accurate execution of all reservation-related activities.

This is a revenue-generating role that requires a strong combination of hospitality, sales ability, technical accuracy, and operational judgment.

The ideal candidate is not simply an order-taker. We need someone who can sell the experience, guide guests toward the right property, overcome objections, and close reservations while protecting the company's financial and operational interests.

What Success Looks Like

A successful Reservation Specialist ensures:

- Incoming inquiries receive prompt, professional responses.
- Qualified booking opportunities are consistently converted into reservations.
- Guests receive accurate property information, pricing, policies, and availability.
- Direct bookings are actively encouraged through approved channels.
- Reservation changes, cancellations, extensions, and payment requirements are handled accurately.
- Every reservation is properly documented and maintained in Guesty.
- Outstanding reservation balances are identified and followed up on.
- Fraudulent, suspicious, or noncompliant reservations are identified and escalated.
- Guest expectations are accurately communicated before arrival.
- Repeat guests and referral opportunities are actively developed.
- Revenue opportunities are not lost because of slow responses or poor follow-through.

Our expectation: The Reservation Specialist owns the booking opportunity from initial inquiry through confirmation and ensures the reservation is accurately handed off for guest servicing.

Core Responsibilities

A. Reservation Sales & Inquiry Conversion

The Reservation Specialist is accountable for maximizing qualified reservation opportunities across StaySouth's portfolio.

Responsibilities include:

- Responding to incoming inquiries through phone, email, website, and approved booking channels.
- Understanding guest travel needs, budgets, preferred locations, dates, and accommodation requirements.
- Recommending suitable StaySouth properties.
- Preparing accurate quotes using approved rates and policies.
- Following up with guests who have not completed their reservations.
- Handling objections regarding pricing, availability, location, and property features.
- Recommending alternative properties when a requested home is unavailable.
- Converting qualified inquiries into confirmed reservations.
- Tracking inquiry sources, follow-up activity, and booking outcomes.
- Identifying opportunities to increase direct-booking conversion.

The Reservation Specialist should approach each qualified inquiry as a potential revenue opportunity.

They must be comfortable asking for the booking, not simply providing information and waiting for the guest to respond.

B. Direct Booking Growth

Direct bookings are an important component of StaySouth's long-term revenue strategy.

Responsibilities include:

- Promoting staysouth.co as an approved direct-booking channel.
- Converting phone, email, and website inquiries into confirmed stays.
- Developing relationships with repeat guests.
- Supporting corporate, group, extended-stay, and travel-agent inquiries.
- Following up with previous guests when appropriate.
- Identifying opportunities to secure future reservations.
- Coordinating approved offers and promotions with leadership and Revenue Management.
- Ensuring reservations are attributed to the correct source.
- Maintaining accurate records of direct-booking revenue and conversion.

All booking activity must comply with applicable channel agreements, approved company procedures, and guest communication policies.

The employee must not circumvent OTA restrictions or promise unauthorized discounts.

C. Reservation Creation & Accuracy

Every reservation must be created and maintained accurately.

Responsibilities include:

- Creating and confirming reservations in Guesty.
- Verifying guest names, contact information, dates, occupancy, and property selection.
- Confirming availability before finalizing reservations.
- Applying approved rates, fees, taxes, deposits, and booking conditions.
- Verifying the correct booking source and payment arrangement.
- Confirming reservation status and guest payment requirements.
- Preventing duplicate bookings and reservation conflicts.
- Reviewing unusual reservation activity and system discrepancies.
- Ensuring guests receive accurate confirmations and next-step instructions.

Reservation accuracy is nonnegotiable.

Errors involving dates, rates, occupancy, payment status, or property selection can result in financial losses, guest dissatisfaction, and unnecessary operational work.

D. Payment Collection & Financial Discipline

The Reservation Specialist is responsible for managing guest-facing reservation payment requirements and coordinating payment-related issues.

Responsibilities include:

- Explaining reservation payment schedules and applicable terms.
- Sending approved payment links and instructions.
- Monitoring outstanding reservation balances.
- Following up on failed, declined, or overdue payments.
- Identifying reservations approaching cancellation deadlines for nonpayment.
- Coordinating discrepancies with Accounting.
- Verifying payment status before confirming payment-dependent actions.
- Documenting collection attempts and guest commitments.
- Escalating payment disputes and chargeback concerns.

The Reservation Specialist does not independently perform accounting reconciliations or release funds.

The role owns guest-facing collection follow-up; the Accounting function own financial reconciliation and accounting accuracy.

No employee should promise a refund, waive a fee, or change a payment obligation outside their approved authority.

E. Reservation Modifications, Extensions & Cancellations

The Reservation Specialist must be comfortable handling changes to existing reservations while protecting revenue and complying with applicable booking policies.

Responsibilities include:

- Processing approved date changes and extensions.
- Reviewing applicable cancellation policies before responding to requests.
- Calculating approved price differences and additional charges.
- Explaining refund eligibility and cancellation terms.
- Processing authorized reservation modifications.
- Identifying opportunities to retain reservations when guests request cancellation.
- Offering suitable alternative properties or dates when appropriate.
- Coordinating cancellation and refund requests with Accounting and leadership.
- Documenting guest requests and outcomes.
- Ensuring reservation changes are accurately reflected in Guesty and relevant booking channels.

Candidates must demonstrate sound judgment and must not make unsupported promises regarding refunds or exceptions.

F. Reservation Screening & Risk Management

StaySouth must protect its homeowners, properties, guests, and financial interests.

Responsibilities include:

- Following approved guest verification and reservation screening procedures.
- Recognizing suspicious booking patterns or inconsistent guest information.
- Reviewing applicable booking restrictions and minimum booking windows.
- Escalating reservations that fail verification or screening requirements.
- Identifying potential unauthorized occupancy or booking-policy violations.
- Documenting screening-related concerns through approved systems.
- Coordinating with leadership before taking actions requiring management approval.

Candidates should understand the importance of consistent policy enforcement, confidentiality, and professional communication.

The employee should never independently discriminate against guests or make screening decisions based on protected characteristics.

G. Guest Experience & Operational Coordination

Although the Reservation Specialist sits within Sales, reservation accuracy directly affects the guest experience.

Responsibilities include:

- Ensuring guests understand booking terms, property rules, occupancy limits, and applicable policies.
- Coordinating reservation-related questions with the Guest Experience team.
- Alerting Operations to unusual arrivals, special requirements, or property readiness concerns.
- Communicating approved reservation changes that affect housekeeping, maintenance, or property access.
- Supporting reservation-related escalations and relocation coordination.
- Ensuring complete reservation information is available to the teams responsible for the guest's stay.

The Reservation Specialist owns booking execution. The Guest Experience Specialist owns routine pre-arrival, in-stay, and post-stay guest communication after the reservation is confirmed.

When one employee fills both seats, the accountabilities must still be measured separately.

H. Systems, Documentation & Process Compliance

StaySouth operates through centralized systems and documented workflows.

Primary systems include:

- Guesty: Reservations, availability, rates, guest records, payment status, and booking modifications.
- GuestyPay: Reservation payment workflows and transaction-status visibility, subject to role permissions.
- Quo: Phone calls, text messages, and guest communications.
- Breezeway: Operational coordination and property readiness visibility.
- GNT: Access-related coordination when reservation changes affect guest entry.
- StaySouth Website: Direct-booking inquiries and reservation conversion.

Responsibilities include:

- Maintaining accurate reservation records.
- Documenting meaningful guest conversations and commitments.
- Following established SOPs.
- Keeping outstanding booking inquiries organized.
- Tracking follow-up deadlines.
- Reporting system discrepancies.
- Escalating operational or financial concerns promptly.
- Identifying opportunities to improve booking workflows and reduce errors.