Outbound Sales Representative – Short-Term Rental Co-Hosting

# Outbound Sales Representative – Short-Term Rental Co-Hosting ABOUT THE COMPANY We are a U.S.-based Short-Term Rental Co-Hosting company that helps Airbnb and vacation-rental owners improve their property’s performance while becoming more hands-off in the day-to-day operation of their rental. Our team assists owners with guest communication, pricing, cleaner coordination, maintenance coordination, listing optimization, reviews, and other operational responsibilities. We are looking for a professional, persistent, and results-driven Outbound Sales Representative to identify qualified short-term rental owners, contact them, develop relationships, and convert interested owners into clients. ABOUT THE POSITION This is an outbound sales position. You will be provided with leads or instructions for identifying potential Airbnb and short-term rental owners. Your responsibility will be to contact those owners, determine whether they need assistance, explain our services, consistently follow up, and schedule qualified appointments. The ideal candidate understands that most prospects will not respond or agree immediately. Success will require professional persistence, organized follow-up, strong communication, and the ability to build trust without becoming aggressive or intrusive. Experience with short-term rentals, Airbnb, vacation-rental management, real estate, property management, or B2B sales is strongly preferred. PRIMARY RESPONSIBILITIES * Contact short-term rental owners through phone, email, text, social media, and other approved channels * Introduce our co-hosting and management services * Ask qualifying questions to understand the owner’s challenges * Determine whether the property meets our minimum requirements * Follow up professionally with owners who are not ready to make a decision * Schedule appointments for qualified and interested owners * Maintain accurate notes for every contact and conversation * Update all lead activity in the company CRM * Track calls, emails, messages, responses, follow-ups, and appointments * Identify objections and provide appropriate responses * Maintain a professional and positive representation of our company * Help improve scripts, outreach methods, and follow-up sequences * Provide daily and weekly activity reports MINIMUM CLIENT QUALIFICATIONS The properties we are targeting should generally: * Generate or have the potential to generate at least $5,000 per month in gross rental revenue * Be owned by someone who needs assistance managing the property * Be a good fit for professional short-term rental management or co-hosting * Have an owner who is willing to pay 20% of gross rental revenue for full-service co-hosting The sales representative should not misrepresent our services or promise specific financial results. WORK SCHEDULE This position may begin part-time or full-time depending on the candidate’s experience. Expected availability: * Part-time: approximately 4 hours per day, 20 hours per week * Full-time: approximately 8 hours per day, 40 hours per week * Monday through Friday * Some working-hour overlap with the United States Eastern Time Zone is required Because this position involves contacting U.S.-based property owners, the selected candidate must be available during appropriate U.S. calling hours. DAILY PERFORMANCE EXPECTATIONS Activity expectations will be established based on the outreach method and quality of the lead list. A typical full-time day may include: * 40–80 outbound calls * 30–60 personalized emails or messages * Follow-up with previous prospects * CRM updates for every lead contacted * Scheduling qualified sales appointments * Providing an end-of-day activity report Quality is more important than simply producing high activity numbers. Generic spam messages, inaccurate notes, fake activity, or poor-quality outreach will not be accepted. HOW PERFORMANCE WILL BE MEASURED Performance will be evaluated using the following key performance indicators: * Hours worked * Number of new leads contacted * Outbound calls completed * Emails and messages sent * Follow-ups completed * Contact rate * Response rate * Qualified conversations * Interested property owners * Appointments scheduled * Appointment attendance rate * Proposals sent * New clients signed * Accuracy of CRM records * Quality and professionalism of communication The successful candidate must be comfortable with measurable performance expectations. ACCOUNTABILITY AND TIME TRACKING To maintain transparency and verify that working hours are being used productively, the selected candidate will be required to use company-approved systems. These may include: * Upwork Time Tracker, Hubstaff, or Time Doctor * A company CRM * Google Sheets * Slack or Microsoft Teams * ClickUp, Monday.com, or another project-management platform * Company email and calling systems All sales activity must be documented in the CRM. The representative will also provide a daily report showing: * Hours worked * Calls completed * Emails and messages sent * Follow-ups completed * Conversations held * Appointments scheduled * Problems or objections encountered * Priorities for the following workday A weekly report will summarize overall activity, results, pipeline status, and recommendations. REQUIRED QUALIFICATIONS * Previous outbound sales, appointment-setting, telemarketing, or lead-generation experience * Excellent spoken and written English * Comfortable making outbound calls * Professional and confident phone presence * Strong follow-up skills * Ability to handle rejection without becoming discouraged * Organized and detail-oriented * Comfortable using a CRM * Reliable internet connection * Quiet and professional work environment * Ability to work independently * Honest and accurate reporting PREFERRED QUALIFICATIONS The strongest candidates will have experience in one or more of the following: * Airbnb * Short-term rentals * Vacation-rental management * Property management * Real estate * Hospitality * B2B sales * Cold calling * Appointment setting * CRM management * U.S.-based customer or client communication COMPENSATION Compensation may include: * Hourly base pay * Performance bonuses * Appointment-setting bonuses * Commission for qualified clients who sign a management agreement Please include your requested hourly rate and any previous compensation structure you have worked under. Compensation will be discussed based on experience, communication ability, sales results, and familiarity with the short-term rental industry. INITIAL TRIAL PERIOD The position will begin with a paid trial period. During the trial, the candidate will be evaluated based on: * Reliability * Communication quality * Ability to follow the sales process * Accuracy of CRM updates * Outbound activity * Quality of conversations * Follow-up discipline * Qualified appointments generated Successful candidates may be offered a long-term position with increased responsibilities and performance-based compensation. HOW TO APPLY Please answer each of the following questions: 1. How many years of outbound sales or appointment-setting experience do you have? 2. Have you made outbound calls to customers or business owners in the United States? 3. How many outbound calls are you comfortable making during an eight-hour workday? 4. What CRM systems have you used? 5. Do you have experience with Airbnb, short-term rentals, real estate, hospitality, or property management? 6. Describe the follow-up process you use when a prospect does not respond. 7. How do you remain persistent without becoming annoying? 8. How do you document your calls and follow-up activity? 9. What is your availability in the U.S. Eastern Time Zone? 10. What hourly rate are you requesting? 11. Are you comfortable using time-tracking software? 12. Please provide a short example of how you would introduce our co-hosting service to an Airbnb owner. Begin your proposal with the words: **“STR Sales Professional”** Applications that do not include this phrase or do not answer the questions may not be considered.