Captain 2

About the Role We are looking for a Captain to join Trip Assist, CREW’s on-trip concierge. You’ll be the person our travelers are actually talking to while they’re on their trip. When they want to know tomorrow’s plan, need a dinner spot, or something goes wrong at the hotel, you’re the one who answers, quickly, warmly and correctly. You’ll be assigned parts of live trips. You’ll build and maintain the trip plans, keep travelers informed through the trip, coordinate with hotels, DMCs, guides and vendors, and close every trip properly once it ends. You’ll report to the Assistant Manager, Trip Assist, and work alongside Senior Captains who lead trips end to end. This is a hands-on, execution-heavy role. You’re measured on how fast and accurately you respond, how smoothly the trip runs, and how the traveler rates the experience at the end. We’re looking for someone who has been on the ground (or on the phone) while a trip was actually happening, knows what breaks, and stays calm and quick when it does. Key Responsibilities ● Build the trip plan: Put together an accurate day-by-day itinerary using our service design. Confirm hotel bookings and research sightseeing, dining and activity options, so every day of the trip is planned and timed.● Add thoughtful touches: Go beyond the template where it makes sense, like a local food recommendation, a re-timed slot based on a group preference, or a fun activity that isn’t on the standard list. ● Respond fast and well: Answer traveler queries within minutes, in simple, warm, easy-to-read language. No walls of text. ● Make information visual: Turn plans into checklists, simple maps and neatly formatted day plans so travelers can take them in at a glance. ● Flag escalations immediately: When something goes wrong (a room issue, a delayed flight, a no-show vendor), raise it to the right person right away with full context: what happened, photos, and the options you’ve already checked. ● Triage and suggest next steps: Judge how serio