A practical playbook for the EA who runs the calendar, manages the cost centers, and handles the call when the driver doesn’t show.

Your phone vibrates at 7:38 a.m. The CEO’s flight was rebooked overnight. He lands at 2:15 instead of 11:30. He needs to be at the board meeting by 4. The current driver pickup is wrong by three hours.

Now, your inbox has 47 unread emails. The team’s Slack is on fire about a client demo. The COO’s spouse is asking about the after-dinner pickup tonight in Cherry Creek. All the while the intern is asking how to forward your phone.

We don’t need to tell you how this is a normal morning for an executive assistant. Ground transportation is one of dozens of decisions you’re managing, but it’s one of the few that can ruin the day if it ever goes wrong. 

A missed pickup, the wrong vehicle, a surprise charge on the expense report. These become your problem, not the vendor’s.

With all your tasks in mind, we’ve created this field guide to make sure ground transportation is the ONE thing that never goes wrong.

What ‘One Text and Done’ Actually Requires

The phrase ‘one text and done’ is what the best executive assistants want from a car service vendor. It means: send one message with the trip details, and the trip happens. You set it and forget it. There is no need to do any follow-ups. You no longer need to second-guess. And you can definitely expect no surprises.

That outcome requires the vendor to deliver four things:

1. Confirmation without follow-up. A text or email back within an hour with vehicle type, chauffeur name, and pickup time. Not ‘we will confirm tomorrow.’
2. Proactive communication. The vendor tells you about flight delays before you have to ask and they confirm 24 hours before. Additionally, the vendor texts when the chauffeur is curbside.
3. Flexibility without renegotiation. Schedule shifts (which happen on every executive trip) are absorbed without a billing dispute. Your chauffeur waits if the meeting runs over.
4. Clean invoicing. The right vendor provides a monthly consolidated invoice with trip details, traveler names, and meeting notes when requested. Not a series of one-off charges.

When a vendor delivers all four, you stop thinking about ground transportation. And that’s exactly the goal.

Before You Book: Vetting the Vendor

Before you put a new vendor on your firm’s preferred list, run them through this short audit:

• Licensing and insurance. Ask for PUC licensing, commercial insurance certificate, and DEN airport permitting in writing. Reputable Denver operators have these ready in a single email.
• Fleet age and maintenance. Ask the age of the vehicles you’d be using. A vendor whose ‘luxury SUV’ is a 2018 with high mileage isn’t the right vendor for board-member transport.
• Chauffeur vetting process. Ask about background checks, driving record requirements, and how long chauffeurs have been with the company. High turnover is a red flag.
• Dispatch responsiveness. Send a test booking inquiry. Track the response time. If it takes 4 hours for a first reply, that’s going to be the case for your day-of experience, too.
• Account references. Ask for two corporate-account references at firms similar to yours. Call them.
• Communication protocol. Confirm how the vendor communicates: text, email, app, or phone. Confirm who you text on the day of the trip.

If a vendor can’t answer all six in a 15-minute call, they’re not a ‘house’ car partner. Keep looking.

At Booking: The 12-Point Pre-Trip Checklist

For every trip, every single time, send the vendor the following 12 data points in one message. 

1. Traveler name(s) and direct contact phone number(s).
2. Pickup date and time. Confirm time zone if booking from outside Mountain Time.
3. Pickup address with suite, apartment, or hotel room number.
4. Drop-off address with floor or suite, if it matters for the building’s loading dock.
5. Flight number and airline if the pickup involves DIA.
6. Number of passengers and rough luggage count.
7. Vehicle type preference (SUV, Sprinter, or Mini Coach) or ‘standard executive default.’
8. Special requirements (car seats, accessibility, pet, and dietary preferences for water or snacks).
9. Stops along the way (grocery, gear, dry cleaning, or restaurant). Each stop comes complete with an address.
10. End-of-trip protocol: hold the vehicle, drop and release, or return trip booked.
11. Billing assignment: which cost center, which executive, which client matters, or which project code.
12. Communication protocol: text you, text the traveler, text both, and who texts first.
13. BONUS for executives with established preferences: any standing instructions (no chatter, conservative news on the radio, specific water brand, no air freshener, seat all the way back, etc.).

All these should already be in the vendor’s saved profile for repeat travelers. For a new vendor, send them at the first booking.

Day-Of: What to Confirm in the 24 Hours Before

24 hours before pickup, confirm:

1. The trip’s still on the vendor’s calendar.
2. The chauffeur is assigned and has the traveler’s contact info.
3. Any timing changes since booking are communicated.
4. The vendor has the flight number in the active flight-monitored system, if applicable.
5. Special instructions are noted in the chauffeur’s brief.

This 5-minute check prevents most ‘the driver never showed’ calls.

In-Flight Communication: Who to Text When Things Change

Plans change. Trips don’t always follow the original timeline. When that happens, here’s our proven communication protocol.

When the change is on your side

Schedule shift, meeting moved, traveler running late, etc.

• Text the dispatch line (faster than calling).
• Include the trip reference number.
• Include the new ETA or new pickup time.

When the change is on the vendor side

Driver running late, vehicle issue, traffic, etc.

• The vendor should text you first, not the other way around.
• If the vendor doesn’t text you proactively, that’s a red flag for the partnership.

The single point of contact (you) should be the only person texting the dispatch line. Group texts on travel days don’t work. The traveler texts you, and you text dispatch to keep everything in one channel.

After the Trip: Reconciliation and Records

After each trip, the vendor should provide:

• A trip receipt with chauffeur name, vehicle, route, and total cost.
• Any additional charges (stops, wait time, gratuity, etc.) should be itemized clearly.
• Mileage and time logged for tax or reimbursement purposes.

For monthly billing, the vendor should provide:

• A consolidated invoice grouping trips by cost center, traveler, or client matter.
• Detailed line items suitable for expense report attachment.
• Net-30 or other agreed payment terms.

When vendors do this, you won’t have to spend hours every month manually finding and cataloging receipts.

Scenario-Specific Add-Ons

Different trips require different add-ons. Here’s what to confirm by scenario.

Board member arrival from DIA

• Flight-monitored pickup with meetup outside of baggage claim.
• Vehicle one tier higher than default (Yukon to Escalade for senior board members).
• Direct route to the meeting venue. No surprise stops.
• Your driver waits at the hotel for the return trip if the meeting includes a same-day return.
• Driver name and photo sent to the board member’s assistant in advance, so they know who is meeting them.

Full executive day in Denver

• Hourly booking with a four-hour minimum.
• Driver waits at each stop. The vehicle stays with the executive.
• Lunch reservation address and contact phone shared at booking.
• Vehicle interior reset between morning and afternoon meetings if there’s a window.
• Standing water and snack preferences pre-loaded.

VIP mountain transfer

• Reference current I-70 conditions before confirming.
• 4WD luxury SUV with mud-and-snow tires.
• Car seats are provided if the VIP is traveling with family (to be installed by client upon arrival). Specify ages and weights at booking.
• Multi-stop coordination (groceries in Frisco, gear in Vail Village, final drop at the lodge, etc.).
• Door-to-door routing, not a parking-lot drop.

Group event transport (off-site, board retreat, client dinner, etc.)

• Sprinter (15-passenger) or Mini Coach (32 or 38) booking, sized to the group.
• One vehicle for the group, not multiple separate rides arriving at different times.
• Pickup zone coordinated with the venue in advance.
• Single point of contact for boarding (you, the planner, or the chief of staff).

What to Look For in a ‘House’ Car Service Partner

The best executive assistants don’t book vendors one trip at a time. They partner with a ‘house’ car service, which is one vendor who knows the executives’ preferences, the firm’s billing protocols, and the building’s loading dock policy.

Signals that a vendor is ‘house’ material:

1. Multi-trip account memory. They remember your CEO prefers no chatter and conservative news on the radio. They remember your CFO needs the seat all the way back. You don’t have to repeat it every trip.
2. A dedicated dispatch contact. Not a different person each time. One name you text, who knows your firm.
3. Consolidated billing. Monthly invoices with detail, not 30 separate charges to reconcile.
4. Vendor responsiveness in minutes, not hours. Confirmations under an hour. Day-of communication near-real-time.
5. A track record on the hard days. The vendor’s behavior during the storm, the closure, the late flight, etc. is what tells you whether they’re ‘house’ material or not. Anyone is good when conditions are easy.

When you find a vendor that hits all five, give them all your business. The premium pricing is worth it when you know you can rely on them for ALL your trips.

What’s Included with a DriveDenver Corporate Account

• A dedicated dispatch contact for your firm. One name, one number, one inbox.
• Saved profiles for each executive (vehicle preference, communication style, special requirements).
• Saved billing assignments by cost center, client matter, or executive.
• Monthly consolidated invoicing with itemized trip details ready for expense attachment.
• Net-30 terms on standard corporate accounts.
• Proactive flight monitoring on every airport pickup. We wait for you when flights are late.
• Meetup outside of DIA’s baggage claim with red-jacket curbside identification.
• Multi-stop hourly bookings with the same chauffeur staying with the executive all day.
• Door-to-door routing on mountain transfers and out-of-town trips.
• Reserved vehicle availability for board weeks, earnings weeks, and high-traffic event dates.
• One text and done. We confirm in minutes, send proactive updates throughout the trip, and invoice cleanly afterward.

Frequently Asked Questions

How do I set up a corporate account?

Send your firm name, billing contact, and rough monthly volume to 303-717-8113. We schedule a 15-minute setup call, create your account profile, and then you’re ready to book by the same week.

Can I book multiple trips at once?

Yes. Send a list of trips in one email and we confirm them as a batch. Most of our weekly EA order volume comes in this way.

Do you support multi-cost-center billing?

Yes. Each trip can be tagged to a different cost center, client matter, or project code. The monthly invoice groups them accordingly.

What is your same-day booking availability?

We accept same-day bookings when our schedule allows. Late-night DIA arrivals and peak event nights book up first. For routine corporate moves, same-day works most of the time.

Can my executive request a specific chauffeur for repeated trips?

Yes. Once we have a chauffeur the executive prefers, we take note of their preference. When the chauffeur is available, they’re assigned by default. When they’re not, we tell you in advance.

Do you handle group bookings for off-sites or board retreats?

Yes. Sprinter and Mini Coach options for groups of 8 to 38. We coordinate with the venue, the planner, and your dispatch contact.

What is your cancellation policy for corporate accounts?

The standard 48-hour policy applies, with corporate-account flexibility for genuinely unavoidable changes. We don’t punish account holders for normal business reality.

Can you integrate with our travel management platform or expense tool?

We work with corporate cards, Concur-compatible receipts, and most major travel management workflows. Specify your platform during the account setup stage and we’ll configure the invoice format to match.

The Bottom Line

Ground transportation is one of the invisible, yet highly crucial, parts of an executive assistant’s job when it works perfectly. However, it’s also one of the most visible parts when it doesn’t.

The difference is the vendor. A vendor that confirms in minutes, communicates proactively, absorbs schedule changes without renegotiation, and invoices cleanly turns any ground transport hiccup into a non-issue. 

For executive assistants running Denver corporate travel, the right vendor relationship is worth more than the per-trip rate. With the right vendor, you have one less thing to worry about. They make you look exceptional and save you the time you would otherwise spend reconstructing the whole day.

Set Up a Corporate Account

Send your firm name, billing contact, and rough monthly volume to 303-717-8113 or accounts@drivedenvercarservice.com. We schedule a 15-minute setup call within 2 business days and then you’re booking by the same week.