Part-Time STR Revenue Optimization Specialist – Airbnb, VRBO, Hostaway & Mailchimp

We are looking for a part-time Short-Term Rental Revenue Optimization Specialist to become a long-term partner in managing the backend performance of our established mountain vacation rental. We currently list on Airbnb, VRBO, and direct through Hostaway, and we use Mailchimp for email marketing. We will continue to handle all guest communication, booking approvals, guest questions, and property operations. This role is focused on revenue optimization, listing performance, channel strategy, pricing, and email marketing. We are specifically looking for someone who can grow into the role, learn the property well, understand our goals, and proactively bring us ideas rather than simply completing assigned tasks. Our Philosophy We are not trying to maximize occupancy at any cost. We want to: - Maximize revenue from the dates we make available - Maintain appropriate pricing floors - Protect the quality of our guest base - Avoid unnecessary discounting or "fire sale" pricing - Improve Airbnb, VRBO, and direct-booking performance - Build a strong repeat-guest and email-marketing strategy We want someone who understands the difference between revenue optimization and simply filling the calendar. Responsibilities - [ ] Manage and optimize our Airbnb listing for search visibility and booking conversion. - [ ] Improve and maintain our existing VRBO listing, which is live but needs attention and stronger performance. - [ ] Manage listing content and channel consistency through Hostaway. - [ ] Review and improve titles, descriptions, photo order, amenities, and other listing elements that may affect search performance and conversion. - [ ] Monitor booking pace, occupancy, ADR, RevPAR, lead time, and important open dates. - [ ] Recommend and manage pricing strategy within agreed-upon minimum pricing floors. - [ ] Recommend and/or implement an appropriate dynamic-pricing tool if beneficial. - [ ] Adjust minimum stays, gap-night rules, lead-time pricing, promotions, and other booking settings when appropriate. - [ ] Identify premium weekends and periods where rates should be increased rather than discounted. - [ ] Identify opportunities to fill shoulder-season dates and calendar gaps without damaging the property's positioning. - [ ] Monitor comparable Wintergreen-area rentals and recommend changes in pricing, amenities, positioning, or strategy. - [ ] Help improve the balance between Airbnb, VRBO, and direct bookings. - [ ] Look for opportunities to increase direct bookings over time. - [ ] Maintain, organize, clean, and segment our existing Mailchimp database. - [ ] Create an ongoing email-marketing calendar. - [ ] Draft email campaigns for our review and approval. - [ ] Schedule and send approved Mailchimp campaigns. - [ ] Create campaigns targeting past guests, seasonal opportunities, open weekends, and repeat-booking opportunities. - [ ] Track open rates, click rates, direct bookings, and campaign performance. - [ ] Review guest reviews and identify recurring themes or opportunities for improvement. - [ ] Recommend listing, pricing, amenity, or property changes when you believe they could improve performance. Weekly Reporting We would like a short, simple weekly update covering: - Current booking pace - Occupancy - Average daily rate - Important upcoming open dates - Pricing changes made or recommended - Airbnb performance observations - VRBO performance - Direct-booking activity - Mailchimp activity and results - Competitor or market observations - Specific recommended actions for the coming week We do not need a long report. We want a concise summary that helps us understand what is happening and what you recommend. What We Are Looking For We are looking for someone who is proactive and analytical. For example, we want someone who might independently notice: - An attractive weekend is still open and needs a pricing or marketing adjustment - VRBO is underperforming and needs listing changes - Several orphan nights could be packaged differently - A group of previous ski-season guests should receive a targeted Mailchimp campaign - Pricing is too low for an upcoming high-demand weekend - A competitor has added an amenity or changed positioning in a way worth paying attention to We do not want to have to identify every opportunity ourselves. Ideal Experience Strong experience with some or all of the following: - Airbnb optimization - VRBO optimization - STR revenue management - Dynamic-pricing platforms - Hostaway - Mailchimp - Direct-booking strategy - Vacation-rental email marketing - ADR, occupancy, RevPAR, booking pace, and lead-time analysis Experience with mountain, ski, resort, or highly seasonal vacation rentals is a strong plus. Time Commitment We anticipate approximately 2–3 hours per week ongoing once everything is optimized. There may be approximately 5–10 additional hours initially to: - Review our current Airbnb and VRBO listings - Improve the VRBO presence - Review Hostaway settings - Review pricing strategy - Recommend or implement a dynamic-pricing system - Organize Mailchimp - Develop the initial email-marketing calendar - Establish the weekly reporting process Compensation We expect the right candidate will likely fall around $12–$15/hour initially. For the right person, we are interested in a long-term relationship, not a short-term project. After the first 60–90 days, we are open to increasing compensation and responsibility for someone who demonstrates strong judgment, initiative, and measurable value. Long-Term Opportunity Our goal is to find someone who eventually knows this property and our revenue strategy extremely well. We value initiative. We want someone who will bring ideas to us, challenge our assumptions when appropriate, and think about the property as a business rather than simply completing a weekly checklist. If you are looking for a very small but long-term STR account where you can become a trusted partner and have meaningful influence over revenue strategy, this may be a good fit. When Applying Please include: 1. Your experience managing Airbnb and/or VRBO revenue. 2. Any experience with Hostaway. 3. Any experience with Mailchimp or STR email marketing. 4. Which dynamic-pricing platforms you have used. 5. An example of a change you made that increased revenue or improved booking performance for a property. 6. Your preferred hourly rate. 7. Your typical availability each week.