Airbnb Supervisor — Business Development & Revenue Management

IMPORTANT — About This Position:
THIS IS NOT A VIRTUAL ASSISTANT POSITION. We are hiring a genuine operations manager who happens to work remotely.
We are looking for an exceptionally intelligent, resourceful, practical, and ambitious person who thinks independently, exercises excellent judgment, and approaches problems as if they were running their own business.
This position will have significant responsibility for supervising our virtual assistants, handling complicated guest issues, overseeing daily operations, and helping grow and improve our business.
A particularly important focus will be Business Development, Revenue Management, Airbnb Listing Management, and Employee Recruitment & Development. You will help identify opportunities to expand our property portfolio, maximize revenue from existing properties, recruit and develop employees, and coordinate the setup of new properties.
We want someone who doesn't simply follow instructions or complete tasks, but understands the bigger picture, solves problems creatively, anticipates future problems, and continually improves how our business operates.
You will directly supervise our Filipino virtual assistants and local US cleaners and maintenance workers during your shifts and report to PBnB ownership/management.
IMPORTANT — Full-Time Commitment & Accountability:
This position requires your full professional attention and commitment during all scheduled working hours. Working for another employer, serving other clients, or performing freelance work simultaneously during PBnB shifts is strictly prohibited.
We are looking for someone who considers PBnB their primary professional commitment. Any other ongoing employment or freelance commitments must be disclosed before hiring and approved by management. Outside commitments must never interfere with your availability, performance, or responsibilities at PBnB.
We take accountability seriously. Employee performance is evaluated through work-quality audits, response-time tracking, task completion records, and other objective performance measures. PBnB may also implement work-activity monitoring software, potentially including time and activity tracking and periodic work-related screenshots during scheduled shifts, with appropriate notice and privacy safeguards.
We respect our employees' personal time and privacy. Our objective is to ensure that everyone is fully engaged, productive, and accountable during the hours they are being paid to work.
If you are looking for a remote position that you can work simultaneously with another job, this position will not be a good fit.
IMPORTANT — Our Approach to Airbnb Support & Guest Disputes:
The short-term rental industry has become increasingly competitive, and Airbnb's policies and support decisions are often unfavorable and unfair to hosts. Protecting our business requires us to be exceptionally strategic, resourceful, persistent, and willing to fight hard for our interests.
We are looking for someone who is tough, assertive, creative, and unafraid of confrontation or challenging authority. You must be comfortable pushing boundaries, questioning decisions, finding unconventional solutions, and using every available avenue to achieve favorable outcomes.
This is not a position for someone who automatically accepts "no" as an answer, blindly follows conventional approaches, or prioritizes pleasing people over protecting the business. We expect you to be a formidable advocate for PBnB, capable of navigating difficult disputes, challenging unfair decisions, and fighting relentlessly for every dollar legitimately owed to us.
We value results, strategic thinking, and the courage to challenge the status quo.
Schedule After Training (US Eastern Time):
Sunday: 10 AM–11 PM
Monday: 10 AM–11 PM
Tuesday: 4:30 PM–11 PM
Wednesday: 4:30 PM–11 PM
Thursday: 4:30 PM–11 PM
Friday: OFF
Saturday: OFF
Total: 42 working hours per week.
Breaks: 30 minutes for shifts of 8 hours or fewer; 60 minutes for shifts over 8 hours (to be taken in 15-minute intervals as able).
Vacation/PTO: 10 PAID Days Off Per Year.
13th-Month Bonus: For every full 12 months of employment completed with PBnB, you will receive an additional bonus equal to one month's regular base salary. This means that for every 12 months you work with us, you effectively earn the equivalent of 13 months of base salary. This bonus is earned only upon completing a full year of employment, beginning on your first employment anniversary and continuing on each subsequent anniversary. It is not paid early or prorated for incomplete years, except where required by applicable law. The advertised monthly salary already includes the annualized value of this bonus.
Training: Training will have flexible hours but typically between 10 AM–10 PM Eastern for 5 days a week and 30–40 hours a week. Training pay is $6 USD per hour. The training duration will depend on how quickly you learn and become fully ready to take on the job (with minimal help), but will be a minimum of 4 weeks and a maximum of 2 months.
Holidays/PTO: No US or Philippine holiday will automatically be a day off, and there is no additional holiday pay under this policy, except where required by applicable law.
Pay Schedule: Paydays are every 4 weeks on Tuesday nights. The pay period ends 2 weeks before payday. Payment takes 1–5 business days to transfer (2 seems most usual).
Company Overview:
Pinnacle Management LLC had humble beginnings, starting in 2018 when Founder Phil Bobbs started renting out the 2nd bedroom in his run-down house in downtown Raleigh occasionally on Airbnb. Eight years and hundreds of thousands of guests later, Pinnacle Management (affectionately called "PBnB" within the company) runs over 50 individual full-time short-term rentals in four cities on the East Coast, and continues to grow yearly.
Primary Responsibilities
1. Business Development & Property Acquisition
A major emphasis of this position is helping PBnB grow by identifying and pursuing profitable new properties and business opportunities.
You will:
Research and identify potential new rental properties in our existing markets and potentially new markets.
Search for houses and apartments suitable for rental arbitrage (renting properties long-term and operating them as short-term rentals).
Research potential property purchases and help identify opportunities to buy homes that would make profitable short-term rentals.
Find and contact landlords, property owners, investors, and other potential business partners.
Explain and present our rental arbitrage or property management proposals to prospective landlords and owners.
Research property rental rates, estimated Airbnb revenue, operating expenses, and potential profitability to help evaluate opportunities.
Follow up with prospective property owners and landlords, build relationships, and help move promising opportunities toward agreements.
Continually look for creative ways to expand PBnB's property portfolio and generate additional revenue.
You do not need to be an experienced real estate investor, but you must be commercially minded, persuasive, resourceful, and capable of researching opportunities and making intelligent business recommendations.
2. Revenue Management & Airbnb Listing Management
Another major focus of this position is maximizing revenue and profitability from our existing properties.
You will:
Regularly monitor the performance of our 50+ short-term rental properties, identifying properties that are not receiving as many bookings as expected.
Investigate possible reasons for poor booking performance, including pricing, competition, reviews, listing quality, photos, amenities, and other factors.
Use PriceLabs and other pricing tools to analyze and adjust nightly rates, discounts, minimum stays, and other pricing strategies.
Help maximize occupancy, nightly revenue, and overall profitability through thoughtful revenue management and yield management.
Monitor property review scores and identify when negative reviews or declining ratings may be affecting booking performance.
Regularly review and improve Airbnb listings, including titles, descriptions, photos, amenities, and other listing details.
Create and duplicate Airbnb listings and ensure that our active and backup listings are properly maintained.
Make sure properties have the necessary backup listings available and ready when needed.
Monitor Airbnb listings and accounts for warnings, flagged photos, restrictions, errors, and other problems that may affect visibility or bookings.
Investigate when a listing may need to be replaced or updated, including determining when a backup listing should be used, subject to Airbnb policies.
Monitor and manage Airbnb host accounts and identify problems requiring attention.
Continually research new strategies and opportunities to improve our listings, booking performance, and revenue.
You should be analytical, detail-oriented, commercially minded, and genuinely interested in discovering why a property is performing well or poorly and what can be done to improve it.
3. New Property Setups, Move-Ins & Move-Outs
You will help coordinate the complete process of launching new properties and closing properties when necessary.
Responsibilities include:
Planning and coordinating the setup of new short-term rental properties.
Arranging utilities, internet service, and other services required for new properties.
Researching, sourcing, and purchasing furniture, appliances, decorations, and household supplies within approved budgets.
Finding good deals on furniture and household items through Facebook Marketplace, Amazon, Walmart, and other retailers.
Communicating with sellers and coordinating furniture pickups and deliveries with local employees, movers, and delivery people.
Scheduling and coordinating movers, cleaners, maintenance workers, photographers, and other people involved in setting up new properties.
Working with local cleaners and setup personnel responsi