The question
How do we handle flights when the team is spread across many cities?
Set a target arrival window rather than booking everyone on the same flights. Group air contracts for your three largest cities, individual ticketing elsewhere, and cluster transfers into three or four departure waves.
Why the arrival window beats the group flight
Remote-first companies rarely have three people in the same airport. Forcing common flights means long layovers, wasted travel days, and inflated fares.
Instead, publish a window — for example, arrivals between 11am and 4pm on day one — and let each attendee book the best routing into it. Transfers run in waves at the top of each hour and nobody sits at the airport for three hours.
When group air contracts make sense
If 10 or more people travel from one city, a group contract usually beats individual fares and adds valuable flexibility.
- Name changes are typically free until 30 days out — decisive for incentive programs with late rosters.
- Deposits are small (often $50–$100 per seat) with the balance due 45–60 days before travel.
- Fares are locked against the increases you would otherwise absorb as the date approaches.
Build the buffer day into the agenda
Never schedule content on the arrival afternoon. Weather and misconnects are normal, not exceptional. Make day one a welcome reception and let the substance start on a full, rested morning.
Key takeaways
- Publish an arrival window instead of mandating flights.
- Group air for cities with 10+ travelers; individual elsewhere.
- Keep arrival day content-free.