Travel

Get a fractional specialist working inside your Kayak for Business account

You already know Kayak for Business fits your travel management needs. What you need is someone to actually run it, keep bookings organized, enforce your travel policy, and make sure nothing falls through the cracks. Trusty Oak's fractional specialists work directly inside your account, handling the day-to-day so your team travels without friction and your finance team gets clean data. This is not a managed travel agency. This is hands-on account work done by a dedicated specialist who knows your preferences and your policy.

What our team does with Kayak for Business

Concrete work our fractional specialists take on inside your Kayak for Business account. No vague promises.

Configure Your Company Travel Policy Settings

We build out your travel policy rules inside Kayak for Business, including approval workflows, spending caps by trip type, and preferred vendor restrictions. Policy configuration is documented and tested against real booking scenarios before it goes live. You get a setup that actually reflects how your company travels, not just default settings.

Book and Manage Travel for Employees or Executives

We handle flight, hotel, and car rental bookings on behalf of your travelers, working within your approved policy parameters. When itineraries change, we manage rebooking, cancellations, and credit tracking so the traveler does not have to dig through confirmation emails. Every booking is logged with trip purpose and traveler details for easy expense reconciliation.

Organize Traveler Profiles and Preferences

We build and maintain individual traveler profiles, including TSA Known Traveler Numbers, seat preferences, loyalty program IDs, and dietary or accessibility notes. Keeping profiles current reduces booking errors and ensures each traveler gets the right options surfaced at checkout. We audit profiles on a recurring basis and update them when employees provide new information.

Audit Bookings for Policy Compliance and Cost Variance

We run regular reviews of completed and pending bookings to flag out-of-policy selections, duplicate charges, and fare variances that need explanation. Audit findings are compiled into a simple report your finance or operations lead can act on without needing to log into the platform. This keeps your travel spend accountable without requiring a dedicated travel manager on staff.

Build Trip Reports and Export Data for Expense Tools

We pull booking and spend data from Kayak for Business and format it for import into your expense management platform, whether that is Expensify, Concur, QuickBooks, or a custom spreadsheet workflow. Reports are structured by traveler, cost center, trip date, or any grouping your finance team needs. We handle the export cadence on a schedule that matches your billing cycle.

Migrate Existing Bookings and Traveler Data Into Kayak for Business

If you are moving from another corporate travel tool or a manual booking process, we handle the data migration: importing traveler profiles, recreating policy rules, and documenting any gaps between your old setup and what Kayak for Business supports natively. We flag anything that requires a decision from your team before going live, so there are no surprises mid-migration. The result is a clean starting point with no orphaned data or missing preferences.

How Trusty Oak supports Kayak for Business workflows

How the Kayak for Business handoff works

During onboarding, your dedicated Client Success Manager reviews your existing Kayak for Business setup, or if you are starting fresh, maps out what needs to be built before your team starts booking. We document your current traveler roster, policy rules, and any integrations with expense or finance tools, then build a prioritized roadmap so work starts on what matters most. Your specialist works directly inside your account and documents every configuration change and workflow so nothing lives only in someone's head. You review and approve the setup before it goes live, and ongoing work follows the same documented process so you always know what was done and why. As your travel volume or team grows, we adjust the scope without requiring you to re-explain your preferences from scratch.

Common Kayak for Business workflows we build

A few of the most common workflows our team has deployed with Kayak for Business.

Trip request submitted, policy checked, booking confirmed

An employee submits a travel request with destination, dates, and trip purpose. We check the request against your Kayak for Business policy settings, book the best compliant option, and send the traveler a confirmed itinerary with all relevant details in one place.

Booking completed, data exported, expense report populated

After a trip is booked or completed, we pull the transaction data from Kayak for Business and push it into your expense tool (Expensify, Concur, or a formatted CSV) with the correct cost center and trip category already filled in. This eliminates the manual data entry step for both travelers and finance.

Flight cancellation, rebooking actioned, traveler notified

When a flight is canceled or a schedule change is issued, we monitor the affected booking, rebook the traveler on the next compliant option, and send an updated itinerary. Credits or refunds are tracked and noted in the traveler profile for future use.

Monthly spend pulled, cost center report delivered to finance

At the end of each billing period, we export all completed travel transactions from Kayak for Business, sort them by cost center or department, and deliver a formatted report to your finance team. The report includes booking dates, traveler names, vendor, and total cost per trip.

New employee onboarded, traveler profile built, policy access granted

When a new hire needs travel access, we create their Kayak for Business traveler profile, enter their loyalty program numbers and preferences, assign them to the correct policy tier, and confirm their access is working before their first trip. This keeps onboarding consistent and prevents last-minute setup requests before a trip.

What Kayak for Business 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 admin access to my Kayak for Business account?

Yes, your specialist needs login access to work inside your account, but access is granted by you and can be scoped to the permissions your platform allows. You retain full ownership of the account and all data at all times. We recommend creating a named user for your specialist rather than sharing a primary admin credential.

How does ongoing Kayak for Business support work after the initial setup?

After the initial policy configuration and profile setup, ongoing work typically covers booking management, compliance audits, report exports, and profile maintenance on a recurring schedule. Your specialist tracks hours against your monthly Trusty Oak budget, and unused hours roll over so you are not penalized for slower travel months. You can adjust the scope of recurring tasks at any time through your Client Success Manager.

Is Kayak for Business the right tool for us, or should we be using something like TripActions or Navan instead?

Kayak for Business works well for small to mid-size teams that want self-service booking with basic policy controls and do not need the full expense management or approval workflow depth of platforms like Navan or SAP Concur. If your team is larger than 50 travelers or you need deep ERP integration, we can flag that during onboarding and help you evaluate whether a migration makes sense. We will not push you to stay on a tool that does not fit your actual needs.

Can a Trusty Oak specialist book travel on behalf of our executives, not just manage the account settings?

Yes, executive travel booking is one of the most common tasks our specialists handle inside Kayak for Business. This includes researching options, booking within policy, managing changes, and tracking loyalty credits and unused ticket credits. If the executive has preferences that fall outside your standard policy, we can document those as exceptions and flag them for your approval rather than booking without oversight.

What does the onboarding process look like for a team that already has Kayak for Business set up?

We start with an audit of your existing configuration, including policy rules, traveler profiles, and any past booking data, to identify gaps, outdated settings, or missing integrations. The audit typically takes the first one to two weeks and produces a short findings document with a prioritized list of fixes and improvements. From there, your specialist begins working through the roadmap on a schedule that fits your monthly hour budget.

Let US take over your Kayak for Business account

Book a discovery call and we will audit your current Kayak for Business setup, identify what is missing or misconfigured, and deliver a prioritized roadmap before any work begins. You will know exactly what your specialist will do and what it will cost.