CEO Operations Associate

Role Description Location: Milan, Italy (remote-friendly, with flexibility for calls with U.S. time zones) Employment type: Full-time Dolce Vita Stays is a growing short-term rental (Airbnb) and property management company operating unique homes across the U.S. and beyond. The mission is to deliver a “Dolce Vita” guest experience while running operations with startup-level speed, efficiency, and attention to detail.​ This role is for someone who loves organizing chaos, closing loops, and making sure “nothing falls through the cracks.” You will be the CEO’s operational right hand, touching everything from property setups and cleanings to permits, damage claims, and guest issues.​ What you will do Day-to-day operations Coordinate cleanings, maintenance, photo shoots, deliveries, and setups across multiple properties and time zones. Liaise with owners, cleaners, handymen, and photographers to confirm schedules and ensure tasks are executed as agreed. Manage logistics such as furniture orders, key shipments, and follow-ups when something goes wrong (lost keys, wrong delivery, returns). Track and follow up on damage claims, city issues, and STR permit applications together with owners and local authorities.​ CEO support and project execution Act as the CEO’s point person for day-to-day execution: organize priorities, keep a clear task list, and make sure things get done on time. Prepare quick updates and recaps on what is happening across properties (issues, status, upcoming deadlines). Help onboard new properties and vendors, keeping documents, contacts, and SOPs updated and easy to find. Spot operational inefficiencies and propose simple process or tool improvements.​ Guest and partner communication Coordinate responses to guest issues and negative reviews with a calm, solution-oriented tone. Maintain clear, professional communication with property owners and local partners, keeping everyone aligned on next steps. Protect the Dolce Vita Stays brand by ensuring properties are guest-ready and issues are proactively handled.​ What we're looking for Exceptional organization and follow-through: you enjoy checklists, structure, and closing open loops. Strong communication skills in English; Spanish is a strong plus given the mix of guests and partners.​ Comfortable working mostly remotely, using tools like Google Workspace, WhatsApp, Notion/Trello or similar. Problem-solver mindset: when something unexpected happens (damage, delays, complaints), you focus on solutions, not excuses. No formal degree required; hospitality, operations, admin, or coordination experience is a plus but not mandatory. Motivation and reliability matter most.​ Attention to details What you get Direct, daily exposure to the founder/CEO and how an international Airbnb arbitrage business is built and scaled. Fast-learning environment with responsibility from day one and room to grow your scope over time.​ Flexible work setup based in Italy, with an international context and frequent interaction with U.S.-based partners.​