Travel

Get a TripIt Pro specialist working in your account

You already know TripIt Pro can handle your travel logistics. The problem is that building clean itineraries, managing connections, and keeping everything synced across your calendar and team takes consistent attention you don't have. Trusty Oak's fractional specialists work directly inside your TripIt Pro account, handling the setup, maintenance, and coordination so your travel plans are accurate before you ever leave the office. This is hands-on account work, not advice about what you should do yourself.

What our team does with TripIt Pro

Concrete work our fractional specialists take on inside your TripIt Pro account. No vague promises.

Build and format master itineraries from raw booking confirmations

When you forward flight, hotel, and car rental confirmations, our specialists parse and organize each segment into a clean, sequenced TripIt itinerary. We add manual segments for ground transportation, dinner reservations, and meeting locations that don't auto-import. The result is a single trip plan with no gaps and no duplicate entries.

Audit and correct existing trips for accuracy and completeness

Itineraries built over time often accumulate outdated segments, duplicate bookings, or missing confirmation numbers. Our specialists review each active trip in your account, cross-reference against your actual bookings, and correct or remove entries that don't match. We flag any discrepancies that require action on your end, such as a rebooking or a missing hotel confirmation.

Configure and manage TripIt Pro alerts and calendar sync settings

We set up your TripIt Pro calendar feed so trips publish correctly to Google Calendar, Outlook, or Apple Calendar with the right event names and times. Alert preferences for flight status, gate changes, and check-in reminders are configured based on how you actually travel. We test the sync after setup and revisit the configuration whenever you change calendar platforms or devices.

Coordinate multi-traveler trips using team sharing features

For executive teams or clients traveling together, we use TripIt Pro's trip-sharing and group itinerary features to make sure each traveler has visibility into shared legs of the journey. We manage who has view or edit access on each trip and update shared itineraries when any booking changes. This keeps a travel coordinator or EA from fielding individual questions about logistics.

Track points, loyalty numbers, and traveler profiles across trips

We maintain your traveler profile in TripIt Pro with current frequent flyer numbers, hotel loyalty IDs, and TSA PreCheck or Global Entry details so they populate correctly on new itineraries. When loyalty numbers change or new programs are added, we update the profile and verify that past trips are tagged correctly. This creates a consistent record that also feeds into TripIt Pro's points and rewards tracking.

Integrate TripIt Pro data with expense and productivity tools

Using TripIt Pro's email forwarding, API connections, or Zapier-based workflows, we connect your itinerary data to tools like Expensify, Concur, Notion, or your team's project management system. A confirmed trip can automatically create a pre-trip checklist, populate a travel expense template, or notify a team Slack channel with your itinerary details. We document each integration so you understand exactly what triggers what.

How Trusty Oak supports TripIt Pro workflows

How the TripIt Pro handoff works

During onboarding, your dedicated Client Success Manager reviews your current TripIt Pro setup, including existing trips, calendar sync configuration, traveler profile completeness, and any integrations already in place. From there, we build a Strategic Delegation Plan that prioritizes the highest-value tasks first, whether that's cleaning up a backlog of past trips, establishing a reliable forwarding and review workflow, or connecting TripIt Pro to your expense or calendar tools. Our specialists work inside your account with credentials you control, and every workflow we build is documented so you always know what's happening and why. You review and approve the approach before we execute, and we check in regularly to adjust priorities as your travel schedule changes.

Common TripIt Pro workflows we build

A few of the most common workflows our team has deployed with TripIt Pro.

Booking confirmation email forwarded to TripIt, itinerary reviewed and corrected, calendar updated

When you forward a confirmation to plans@tripit.com, our specialist checks the auto-parsed itinerary within 24 hours for accuracy, adds any missing segments, and confirms the trip appears correctly in your synced calendar. This prevents the common problem of TripIt misreading hotel check-in times or flight layovers.

Flight change notification received, itinerary updated, downstream calendar and team alerts sent

When an airline reschedules a flight, we update the affected segment in TripIt Pro, check whether connecting segments or hotel check-in times are now misaligned, and notify relevant team members or a travel coordinator via Slack or email. No detail falls through because of an unread airline email.

New trip created in TripIt Pro, Expensify expense report pre-populated with travel dates and categories

Using a Zapier workflow connected to your TripIt Pro account, a confirmed itinerary triggers the creation of a matching expense report in Expensify with travel dates, destination, and category fields pre-filled. This reduces manual entry at the end of a trip and keeps expense submissions timely.

Monthly travel history exported, loyalty point balances logged, summary delivered to client

At the end of each month, our specialist pulls your completed trips from TripIt Pro, logs the associated airline and hotel stays against your loyalty accounts, and delivers a one-page summary showing trips taken, miles accrued, and any rewards approaching expiration. This gives you a clear picture without logging into five separate airline portals.

Multi-city executive trip planned, individual traveler itineraries built and shared, ground transport segments added manually

For a trip covering three cities with two executives traveling on different legs, we build separate TripIt itineraries for each traveler, share the relevant segments between them, and manually add car service pickups and venue addresses that don't come from booking confirmations. Each traveler has a complete, accurate itinerary without needing to coordinate with each other.

What TripIt Pro support costs

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

Executive Assistants

~$35/hour

10 hours $350

Specialists

~$50/hour

20 hours $1,000

Fractional Executives

~$95/hour

0 hours $0

Your monthly budget

$1,350

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

Book a Discovery Call

Frequently asked questions

Do I have to give Trusty Oak access to my TripIt Pro account?

Yes, our specialists work directly inside your account, so you'll need to share login credentials or set up a team access method. TripIt Pro's team features allow you to add users without sharing your primary password in some configurations. You retain full ownership of the account at all times, and access can be revoked immediately if you end the engagement.

Is this a one-time setup or ongoing monthly work?

Most clients use TripIt Pro support on an ongoing basis because travel logistics change constantly, bookings get rescheduled, and new trips need to be processed as they're booked. Our monthly talent budget starts at $1,000 per month, and unused hours roll over, so lighter travel months don't go to waste. We can also scope a one-time audit or setup project if that's all you need before deciding on ongoing support.

How quickly can a specialist start working in my TripIt Pro account?

After the one-time onboarding call and Strategic Delegation Plan are complete, typically within the first week, your specialist can begin working in your account immediately. The onboarding process includes a $300 one-time fee and is designed to make the first task handoff as efficient as possible so you're not spending time explaining context repeatedly.

Is TripIt Pro the right tool for my travel management needs, or should I be using something else?

TripIt Pro is well suited for individual executives or small teams who book their own travel and need a reliable way to consolidate and share itineraries. If your organization needs centralized booking controls, policy enforcement, or direct integrations with a corporate travel management system, tools like Concur or TravelPerk may be a better fit. Our specialists have experience across travel and productivity tools and can give you an honest assessment during onboarding if you're not sure TripIt Pro is the right choice.

What happens to my TripIt Pro workflows if I pause or cancel my Trusty Oak subscription?

Everything our specialists build lives inside your TripIt Pro account and any connected tools, so nothing disappears when the engagement ends. We document all integrations and workflows in a format you can hand off to another team member or pick up yourself. The initial three-month commitment gives us enough time to build and stabilize your setup before you decide whether to continue month-to-month.

Let's audit your TripIt Pro setup

Book a discovery call and we'll review your current TripIt Pro configuration, identify gaps in your itinerary workflow, and outline a prioritized plan for what a specialist would tackle first.