Sales, Owner Acquisition & Operations Coordinator

Sales, Owner Acquisition & Operations Coordinator Remote Contractor | Colombia or Latin America Preferred | Full-Time Opportunity Naples Florida Vacation Homes is a family-owned vacation rental management company based in Naples, Florida. We manage a curated portfolio of vacation homes and are known for responsive, personal service to both guests and property owners. We are looking for a proactive, highly organized Sales, Owner Acquisition & Operations Coordinator to help us increase direct bookings, improve lead follow-up, grow our portfolio of managed vacation homes, and support daily operations while our COO is managing properties in the field. This is not a basic customer-service or virtual-assistant role. We are looking for someone who is commercially minded, confident communicating with U.S.-based guests and property owners, and capable of managing follow-up, organization, outreach, and problem-solving without needing constant direction. This role will begin as a contract position through Upwork, with the intention of becoming a long-term, full-time position for the right person. Primary Goal of This Role Your main responsibility will be helping create more revenue opportunities for the company through: - Converting more guest inquiries into confirmed bookings. - Following up consistently with unbooked leads and past guests. - Identifying and developing relationships with prospective vacation-rental owners. - Supporting the COO with important remote operational tasks when she is onsite at properties. You should be comfortable balancing sales follow-up, outbound calling, owner lead generation, guest communication, reporting, internal task management, and day-to-day problem-solving. Guest Sales & Reservations Responsibilities - Respond quickly and professionally to new direct booking inquiries, calls, emails, and quote requests. - Call prospective guests who have requested information, received a quote, or have not completed their booking. - Follow up consistently with unbooked inquiries according to our sales process. - Prepare and send personalized quotes, availability options, and booking recommendations. - Help guests choose the right property based on their group size, travel dates, location preferences, and needs. - Build rapport with guests while maintaining a warm, polished, hospitality-focused communication style. - Track all inquiries, calls, quotes, follow-ups, and outcomes accurately in our systems. - Identify opportunities to recover abandoned inquiries or bookings before they are lost. - Follow up with past guests regarding future stays, repeat bookings, seasonal travel, and special offers. - Help improve our response time, quote follow-up process, booking conversion rate, and direct booking revenue. - Communicate closely with the reservations team to ensure inquiries and guest needs do not fall through the cracks. Owner Acquisition & Business Development Responsibilities A major part of this role will be helping Naples Florida Vacation Homes grow its portfolio by developing relationships with prospective property owners. Responsibilities will include: - Researching and identifying potential vacation-rental owners and investment-property owners in our target market. - Building and maintaining organized prospect lists using approved lead sources, public information, referrals, networking opportunities, and company-provided leads. - Making outbound calls, sending personalized emails, and following up with prospective owners professionally and consistently. - Explaining our company’s value proposition, guest-service standards, marketing approach, operational support, and property-management services. - Qualifying prospective owners based on property type, location, condition, rental potential, timing, and fit with our management program. - Scheduling calls, property walkthroughs, or consultations for the COO and leadership team. - Maintaining clear CRM notes, outreach records, follow-up dates, lead status, and next steps for every owner prospect. - Preparing owner prospect summaries before meetings, including property details, rental-market information, concerns, questions, and relevant background. - Following up after owner meetings to keep conversations moving forward. - Tracking pipeline activity and reporting on leads generated, conversations held, appointments set, proposals sent, and signed management agreements. - Assisting with owner-facing materials, proposal preparation, presentations, and follow-up communication when needed. - Identifying patterns in owner objections and recommending ways to improve our sales process, messaging, and marketing materials. This role is not expected to independently close every owner agreement at the beginning. However, the right candidate should be comfortable opening conversations, building trust, maintaining consistent follow-up, and helping move qualified prospects toward a meeting with leadership. Operations & Executive Support Responsibilities This role will also support the COO with remote operational tasks, particularly when she is onsite at properties and cannot be at a computer. Responsibilities may include: - Organizing daily priorities, open tasks, follow-ups, and reminders. - Communicating with maintenance, housekeeping, vendors, and guest-services team members when follow-up is needed. - Assisting with reservation audits, guest notes, property information updates, and internal documentation. - Preparing summaries of guest issues, maintenance concerns, owner-related items, or unresolved tasks requiring leadership attention. - Following up with vendors, collecting quotes, confirming appointments, and documenting updates. - Organizing files, spreadsheets, reports, checklists, and internal documents. - Helping prepare owner communications, guest-service communications, property updates, and internal task lists. - Monitoring team follow-up and ensuring important items are completed or escalated. - Helping maintain organization across reservations, sales, owner acquisition, guest service, marketing, operations, and leadership priorities. - Taking initiative when you see an issue, missed follow-up, incomplete task, or opportunity for improvement. Schedule This role requires substantial overlap with U.S. Eastern Time business hours. Preferred schedule: Approximately 10:00 a.m.–7:00 p.m. Eastern Time, Monday through Friday A mutually agreed schedule may be possible, but you must be available during core U.S. daytime business hours for guest calls, owner outreach, follow-up, and team communication. Candidates based in Colombia or another Latin American country with strong Eastern Time overlap are preferred. What We Are Looking For - Excellent spoken and written English with clear, polished, professional communication. - Comfortable speaking with U.S.-based guests and prospective property owners by phone. - Proven experience in sales, lead generation, business development, reservations, hospitality, real estate, travel, property management, customer success, or lead conversion. - Strong outbound calling and follow-up habits. - Confidence starting conversations with prospective clients and building rapport without sounding scripted or overly aggressive. - Highly organized, proactive, detail-oriented, and comfortable managing a sales pipeline. - Able to work independently, think ahead, and make good judgment calls within clear company procedures. - Strong computer skills, including Google Workspace, spreadsheets, CRM systems, project-management tools, and communication platforms. - Experience with vacation rentals, hotels, property management, real estate, travel, or home services is strongly preferred. - Experience supporting a U.S.-based business is a plus. - Reliable internet connection, quiet workspace, and professional phone setup are required. What Success Looks Like Success in this role will be measured by: - Faster response times to new guest inquiries. - Consistent follow-up on every quote and unbooked lead. - Improved direct-booking conversion rates. - A growing and well-maintained owner-acquisition pipeline. - Consistent owner outreach, follow-up, and qualified appointments scheduled for leadership. - Clear CRM notes, pipeline tracking, and reliable reporting. - More organized daily operations and fewer tasks requiring last-minute intervention from leadership. - Strong communication, reliability, initiative, and ownership. Compensation Structure We are open to an hourly contractor rate during the initial trial period, with the potential for a long-term full-time role. For the right candidate, compensation may include performance-based incentives tied to measurable results, such as: - Qualified owner appointments scheduled. - Signed property-management agreements. - Direct bookings generated or recovered through follow-up. - Consistent completion of sales and operational performance goals. Contract Structure We plan to begin with a paid trial period through Upwork. During the trial, we will evaluate communication skills, sales ability, phone presence, owner-outreach ability, follow-up discipline, organization, reliability, initiative, and overall fit with our company. The right person will have the opportunity to transition into a long-term, full-time contractor role with increasing responsibility and performance-based earning potential. To Apply Please include the following in your proposal: 1. A brief introduction explaining why you are a strong fit for a sales, owner acquisition, and operations role. 2. Your experience with phone sales, lead generation, business development, reservations, hospitality, property management, travel, real estate, or customer conversion. 3. A short example of how you would follow up with: - A guest who received a quote but has not booked; and - A prospective property owner who expressed interest but has not scheduled a call. 4. A short audio or video introduction in English. 5. Confirmation of your availability during U.S. Eastern Time business hours. 6. Your preferred hourly rate and availability for a long-term, full-time contractor role. 7. Examples of the systems you have used, such as CRM platforms, reservation software, Google Workspace, spreadsheets, project-management tools, lead-generation tools, or phone systems. To confirm that you read the entire posting, please begin your proposal with: "Every opportunity deserves thoughtful follow-through.” We are looking for someone who wants to become a trusted part of our company. Someone who can help us sell more effectively, grow our owner portfolio, stay organized, and deliver the level of personal service our guests and owners expect.