Travel coordination without the Back-and-Forth

Booking a multi-leg business trip can take two to four hours when you factor in comparing flights, cross-referencing hotel locations, building a usable itinerary, and handling the inevitable changes. Trusty Oak Executive Assistants take that off your plate entirely — managing the research, bookings, and real-time adjustments so your calendar reflects a trip that actually works. Across 67 logged time entries in this category, our EAs have handled everything from routine domestic trips to complex international travel with multiple travelers.

What your executive assistant handles

Concrete tasks our team takes on — not vague promises.

Flight Research and Booking

Your EA searches across Google Flights, Kayak, or your preferred OTA to find the best routing and price for your schedule, then books directly or through your existing corporate travel account.

Hotel and Accommodation Sourcing

Beyond just finding availability, your EA vets hotels against your actual meeting locations, checks loyalty program compatibility, and confirms cancellation policies before booking.

Ground Transportation Coordination

Your EA arranges airport transfers, rental cars through platforms like Enterprise or National, or ride-share scheduling so there are no gaps between arrival and your first commitment.

Itinerary Building and Distribution

Your EA compiles all confirmations, addresses, contact numbers, and timing into a single clean itinerary document — typically in Google Docs or TripIt — that you can access offline or share with your team.

Change Management and Rebooking

When flights get canceled or meetings shift, your EA handles the calls, rebooking, and itinerary updates so you're not spending an hour on hold with an airline.

Travel Policy and Expense Prep

Your EA tracks booking costs, saves receipts, and organizes expense documentation in tools like Expensify or Concur so reconciliation doesn't pile up after the trip.

$Trusty Oak fractional talent services$

How the handoff works

During onboarding, your Client Success Manager builds a Strategic Delegation Plan that captures your travel preferences upfront — preferred airlines, seat preferences, loyalty program numbers, hotel brands, budget parameters, and any standing policies. From there, you hand off a trip request the same way you'd send a quick email or Slack message: destination, dates, purpose, and any constraints. Your EA handles everything from that point and returns a complete itinerary for your review before anything is finalized. Most clients are fully handed off within the first week, with their EA already managing an active trip by day ten.

Tools our team works with

We adapt to your existing stack — no forced migrations.

Google Flights

TravelPerk

Expensify

Concur

TripIt Pro

Kayak for Business

...and many more!

What travel coordination support costs

Drag the sliders to build a monthly plan that fits your workload.

Executive Assistants

~$35/hour

25 hours $875

Specialists

~$50/hour

5 hours $250

Fractional Executives

~$95/hour

0 hours $0

Your monthly budget

$1,125

Starting at $1,000/month. One-time $300 onboarding fee includes your Strategic Delegation Plan.

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Frequently Asked Questions

Do I need to give my EA access to my credit card or travel accounts?

Most clients share a dedicated corporate card number or use a virtual card for travel bookings, and provide read or booking access to their loyalty accounts as needed. Your EA will only book what you've approved — nothing is finalized without your confirmation unless you've explicitly set standing approval rules.

What happens if my flight gets canceled while I'm already traveling?

Your EA can monitor itineraries through TripIt Pro and respond to disruptions in real time during business hours. If you need coverage outside standard hours, that's worth discussing during onboarding so expectations are set clearly from the start.

Can a Trusty Oak EA handle travel for multiple people on my team?

Yes — coordinating group travel, including aligning flight times, shared accommodations, and consolidated itineraries, is something our EAs handle regularly. The complexity is manageable as long as traveler preferences and approvals are clearly communicated upfront.

How many hours does travel coordination typically use each month?

It depends on trip frequency and complexity, but a single domestic round trip with hotel and ground transport typically takes two to three hours to research, book, and document. Clients who travel two to three times a month often use six to ten hours on travel coordination, leaving the rest of their monthly budget for other tasks.

Hand off your next trip

Monthly plans start at $1,000 with a one-time $300 onboarding fee — and unused hours roll over. Tell us what you're working with and we'll match you with the right support.