Director of Tour Operations

What you'll do: Lead tour delivery end-to-end Be accountable for every departure from contract to wheels-up: vendor bookings, payment schedules, guest logistics, contingency plans Run our milestone-based tour readiness system for every departure and improve it Run overlapping departures in peak season, such as a group in Rome while another lands in Florence, without any guest ever feeling it Build the operating system Document, systematize, and continuously improve every operational workflow: SOPs, checklists, vendor playbooks, tour-manager runbooks Design the operations that let us add new regions and departures without the founders on every call Lead operational reporting: tour readiness, cost management, vendor performance, guest satisfaction Manage vendors & ground partners Establish and maintain relationships with hotels, restaurants, guides, drivers, and experience providers across multiple Italian regions Negotiate contracts, lock rates well in advance, and manage payment schedules across currencies Line up backups for every critical partner, so a closed restaurant or a cancelled driver never breaks a guest's day Build the ops team Hire and lead the ops team, including tour managers and coordinators, who will own pieces of the operation under your direction What we'd like to see 5+ years of experience running complex, deadline-driven, multi-vendor operations in travel, events, hospitality, or an adjacent field Proven system-builder: you can show us a process you documented and handed off so completely that it survived your absence Experience managing external vendors and negotiating contracts Obsessive attention to detail and a steady hand under pressure. Our guests have waited years for this week, and it has to be flawless. Excellent written communication Self-directed and comfortable owning outcomes without daily oversight Able to travel to Italy occasionally during tour seasons Bonus qualifications Experience scaling operations at a fast-growing small company Reasons not to take this job You need a department to hand things off to. We're a small team, and there's no travel desk, legal team, or finance group behind you. You're only willing to do the bare minimum. Peak seasons are intense, with multiple departures running close together. You'd rather not be held to a high bar. Our guests expect excellence, and so do we. You want to run systems someone else built. Here, you'll be building them. You're here for the travel perks. The job is delivering a magical week for our guests. Time in Italy is a perk of the job, not the reason for it.

Compensation & benefits: Competitive salary depending on experience Health benefits Paid time off, plus company holidays Work laptop and home-office setup, on us Coworking space reimbursement Travel to Italy during tour seasons, fully coveredA front-row seat to building a category-defining company