Invoicing Assistant for Vacation Rentals

THE CONTEXT We are a premium vacation rental management company based in Martinique (French Caribbean). We manage around 40 villas, apartments and bungalows on behalf of their owners. Each guest arrival generates an invoice to the property owner, collected by direct debit. We are looking for a freelancer to prepare these invoices, on a 6-month renewable contract. About 3 to 4 hours per week, remote, in ONE fixed weekly session: every Monday. WHAT YOU WILL DO, EVERY MONDAY - List all guest arrivals of the past 7 days (Monday to Sunday) from our property management software and record them in our tracking register - Prepare the invoice for each owner: four standard lines, with amounts read from a validated rate sheet for each property — never calculated, never estimated - Proofread each invoice, then send it to the owner - File each reservation folder in our Google Drive: booking confirmation as PDF and invoice, following an existing naming convention - Report anything outside the standard process in a written weekly summary Volume: roughly 8 to 16 invoices per week depending on the season. Allow about twelve minutes per file once you know the process. WHAT YOU WILL NOT DO — AND THIS MATTERS You will have no access to our payment tools. Direct debits, payment tracking and reminders stay with the managing director. This is an invoicing and filing mission: demanding on accuracy, with no financial decision in your hands — and no liability on that side either. WHAT MAKES THIS MISSION DIFFERENT Everything is already written down. At signature you receive a complete reference procedure: source hierarchy, tracking statuses, special cases already decided, message templates, and the list of acts you will never have to decide alone. You never have to guess. A 20-minute weekly check-in with the managing director, based on indicators — not a file-by-file review. THE RULES - A fixed weekly deadline: all arrivals of the past week are invoiced and filed by end of day every Monday, Martinique time (UTC−4). Within that day, you organise your time as you wish. - Regularity is non-negotiable: a missed Monday delays the invoicing of a whole week. If you cannot commit to this day every week, please do not apply. - Six acts are reserved for the managing director: discounts, credit notes, commercial gestures, rate changes, waiving a debt, and any change of bank details. In practice, only one will come up for you: applying an amount that is not on the rate sheet — you never do it, you report it. - Reporting a doubt is the expected behaviour, and it is valued. We prefer a three-minute exchange to a credit note and an unhappy owner. THE PROFILE - At least two years in invoicing, sales administration, accounting assistance or back-office - Accuracy over speed: quality here is measured by the absence of errors - Ability to apply a written procedure without interpreting it - Care in document filing: half of the job is putting documents in the right place, under the right name - FLUENT FRENCH: all documents, owners and exchanges are in French - Comfortable with an online invoicing tool and a spreadsheet - Identity verified on Upwork — this is a requirement, as the mission involves our owners' data Nice to have: Pennylane or vacation rental software experience, managed real estate background, a time zone compatible with the Caribbean. CONDITIONS 6-month contract, one monthly milestone, review at 3 months, 30-day trial period. Fixed monthly fee covering a defined volume of files, with a unit price above that volume — the exact volume will be shared before you quote. Gradual onboarding over four weeks: first session in observation, then each invoice reviewed before sending, then autonomy. Named access to our tools is provided. NDA signed before any access is granted. Everything goes through Upwork: contract, messages and payments. Expected start: November 2026. HOW TO APPLY Tell us in a few lines about your invoicing background, then answer this: how would you secure your Monday session every week, including when you are sick or on holiday? Shortlisted candidates take a 30-minute written case study — four real situations from our business — then a video interview. We reply to every application.