Short-Term Rental Pricing Strategist & Operations Manager — Booking.com & Airbnb

We are a family-owned short-term rental business based in Northern Greece (Thessaloniki coast). We operate 2 beachfront apartments in the Thessaloniki area of Northern Greece, both connected on ---------- with 9.8+ guest review scores. We are launching on Airbnb soon. The business is run by a brother-and-sister team — we handle everything on the ground ourselves (guest experience, cleaning, check-ins, maintenance). What we are missing is someone with real strategic expertise who can build our pricing strategy AND make sure the day-to-day operations behind the scenes run smoothly.
We are not a corporation. We are a family that takes pride in our properties and our guests. We are looking for someone who treats this like a partnership, not just a task list. If you are the kind of person who genuinely enjoys figuring out why one listing outperforms another and what to do about it — and who also gets satisfaction from knowing the numbers are accurate and the calendar is tight — you will enjoy working with us.
ABOUT THE ENGAGEMENT
This role has two phases:
Phase 1 — Setup, Strategy Build & Systems Check (First 10–20 days)
This phase will be heavier in hours (15–20 hours/week). During this time, you will audit our full ---------- setup, conduct deep competitor research, review our current pricing and rate structure, and deliver a complete pricing strategy and operational recommendations for both apartments. You will also check that our ---------- infrastructure is solid — extranet settings, rate plans, calendar configuration, payment setup, promotion structure, cancellation policies, and anything else that needs to be cleaned up or optimized. You will learn our P&L tracking system and begin logging reservation data accurately. Both apartments are connected on ---------- , so you need to understand how multi-property setups work.
Phase 2 — Ongoing Summer Operations (4 months: June–September)
If the strategy you deliver in Phase 1 is strong and we work well together, you stay on as our Apartment Pricing, Strategy & Operations Manager for the full summer season. During this phase, hours will be 10–15 per week depending on the needs. You will own weekly competitor monitoring, rate adjustments, performance reporting, calendar management, P&L tracking, and ongoing strategic recommendations. Peak summer in our area is intense — high demand, fast-moving competitor pricing, and every night counts. We need someone who stays sharp throughout and keeps the machine running behind the scenes.
WHO THIS ROLE IS FOR
This role is for someone who has spent at least 2 years inside the ---------- and/or Airbnb ecosystem from the host or property management side. Someone who already knows how discount stacking works, how Genius and mobile rates affect visibility, how to read the Booking extranet analytics, and how to build a pricing strategy that balances occupancy with profit. Someone who can look at 10 competitor listings and tell us exactly where we stand and what to do about it. And someone who understands that strategy means nothing if the calendar has errors, the P&L is wrong, or a reservation falls through the cracks.
We do not need ideas on a whiteboard. We need someone who turns expertise into action — specific rate recommendations, specific changes to our extranet, specific moves based on what competitors are doing this week — while also making sure the operational foundation underneath is solid and accurate.
WHO THIS ROLE IS NOT FOR

This is NOT a general virtual assistant position. We are not looking for someone to only answer guest messages or do basic admin.
This is NOT for someone who has only managed social media or written listing descriptions. We need analytical thinking and operational precision, not copywriting.
This is NOT for someone who will wait for us to tell them what to do. We need someone who brings the plan to us and keeps the business running proactively.
This is NOT for beginners who want to "learn about short-term rentals." We need proven hands-on experience.

If you cannot explain the difference between effective discount percentage and nominal discount percentage, or you have never built a competitor pricing comparison, or you have never maintained a financial tracker for a rental property, this role is not the right fit.
WHAT YOU WILL OWN

---------- Infrastructure Audit & Setup


Review our full ---------- extranet setup for both connected apartments
Check and optimize: rate plans, room configuration, cancellation policies, payment settings, promotion structure, Genius and mobile rate setup, calendar accuracy, content completeness
Identify anything that is misconfigured, missing, or hurting our visibility and conversion
Deliver a clear list of fixes with priority order and implement them (or guide us through implementation)


Competitor Research & Market Intelligence


Identify and track our top 10–12 competitors in the Perea / Neoi Epivates / Thessaloniki coast area
Build and maintain a competitor tracking report: nightly rates (weekday/weekend/seasonal), discount strategies, review scores, listing quality, amenities, occupancy patterns
Update this research weekly and deliver a brief written summary of what changed and what it means for us
Monitor new listings entering our market and flag any threats


Pricing Strategy & Rate Architecture


Develop a full pricing plan for both apartments across the year: peak season, shoulder season, off-season, holidays, weekends
Recommend our base nightly rates, discount structure (Genius, mobile, non-refundable, weekly, monthly), and minimum stay rules
Advise on when to activate or pause specific promotions and rate plans
Analyze how our current pricing is performing — are we leaving money on the table or pricing ourselves out?
Deliver a monthly pricing review with clear, actionable recommendations


P&L Tracking & Financial Operations


Log every reservation into our P&L tracking spreadsheet accurately and completely (we have a detailed model already built with Greek tax logic — environmental fee, city tax, VAT, commission, bank charges, utilities, cleaning, maintenance reserve, and income tax)
Ensure the numbers match what ---------- and Airbnb report — no discrepancies, no missing reservations
Track net profit per reservation and per night for each apartment separately
Maintain the monthly summary and year-to-date financial view
Flag any reservation where the net profit falls below our minimum target so we can investigate and adjust
Deliver a clean, accurate monthly P&L report for each apartment and combined


Calendar & Booking Operations


Keep the ---------- and Airbnb calendars accurate and synchronized at all times — zero double bookings
Review upcoming reservations weekly: confirm dates are correct, rates match our strategy, no conflicts or errors
Flag check-in/check-out overlaps that could create turnover problems (e.g., same-day checkout and check-in with no cleaning window)
Monitor for cancellations and immediately flag freed-up dates so we can adjust pricing to resell them
Ensure the overall apartment management flow runs smoothly from a systems perspective — if something is broken or inefficient in the booking pipeline, we expect you to catch it and raise it


Revenue Reporting & Performance Tracking


Track our key metrics: ADR, occupancy rate, net revenue per night, effective discount %, commission impact
Flag occupancy gaps early and recommend tactical rate adjustments to fill them
Provide a monthly performance report comparing our actual results to competitor benchmarks and to our own targets


Strategic Advisory


Deliver a 90-day pricing roadmap based on your initial competitor research and market analysis
Recommend which ---------- programs and promotions are worth participating in and which are not
Advise on our Airbnb launch pricing strategy
Identify opportunities we are missing — country rates, early-bird discounts, last-minute deals, minimum stay optimization

WHAT WE PROVIDE

Full access to our ---------- extranet and Airbnb dashboard
A detailed competitor research spreadsheet template (ready to use)
A complete financial P&L model with Greek tax logic built in (you do not need to build it — you need to maintain it accurately)
A revenue calculator that models discount stacking, commission, and net profit
Owners who are engaged, responsive, and act fast on good recommendations
A family business environment where your work has direct, visible impact

GROWTH OPPORTUNITY
We want to be transparent about what this could become. If this engagement goes well over the summer, there is a real opportunity to grow beyond our two apartments. We are connected with other property owners in the same area who are interested in professional pricing, strategy, and operations support for their own ---------- listings. We would be happy to introduce you and help you build a client base in our market. The right person could turn this into a steady, multi-property engagement across the Thessaloniki coast. But first, let us see what you can do with our two.
REQUIREMENTS

Minimum 2 years of hands-on experience with ---------- and/or Airbnb from the host, co-host, or property management side
You have personally set up or managed rate plans, promotions, and pricing strategies (not just guest messaging)
You have maintained financial records, P&L tracking, or revenue reporting for rental properties
Strong analytical skills — you are comfortable with spreadsheets, data, and numbers
Detail-oriented and accurate — our P&L model has precise tax calculations and we need the data entered correctly
You can write a clear, concise report in English that a non-technical person can understand and act on
Reliable internet and availability to overlap with European time zone (CET) for regular check-ins

PREFERRED

Experience with PriceLabs, Beyond Pricing, Wheelhouse, or AirDNA
Experience with European or Mediterranean short-term rental markets
Understanding of OTA commission structures and how they affect net revenue
Experience managing pricing and operations across multiple connected properties on ----------
Experience with multi-platform calendar synchronization

WHAT WE EXPECT

Week 1–2: Complete ---------- infrastructure audit and competitor research delivered for both apartments. P&L tracker set up with all existing reservations logged.
Week 3–4: Full pricing strategy and rate architecture recommended, with specific numbers and rate plans. Calendars verified and synced.
Month 2: Weekly competitor updates and calendar checks running on schedule. P&L tracker accurate and up to date. First monthly performance and financial report delivered.
Month 3: Measurable improvement in either ADR, occupancy, or net revenue per night compared to Month 1. Clean financial records with zero discrepancies.

HOW TO APPLY
Send us:

Which ---------- or Airbnb properties you have managed — how many listings, and what was your specific role in pricing, strategy, and operations (not just guest communication or cleaning coordination)
One example of a pricing decision you made that improved revenue or occupancy — what did you change, why, and what was the result
Have you maintained P&L records or financial tracking for rental properties? If yes, briefly describe what you tracked and how
Your availability and expected hourly rate

Short, specific answers beat long generic ones. We read every application carefully.