Most companies pick a ground transportation provider the same way they pick a stapler supplier: somebody needs a car, somebody books one, and it becomes the default. Then it fails at the wrong moment, and the review starts.

This is what to check before that happens. It is written for whoever owns travel inside a business — an office manager, an EA, a travel coordinator, or a finance lead who has noticed the ride-hailing line on the card statement.

The Questions That Actually Matter

1. Is the price fixed, and fixed when?

Ask whether the rate is agreed before the trip or calculated after it. This sounds obvious and it is where most of the unpleasant surprises live.

Then ask the harder version: does the rate change on high-demand dates? In Indianapolis that means race weekend, convention weeks and bad weather. A provider who quotes flat and means it will say so plainly. One who hedges is telling you something.

Watch for the extras that appear later — fuel surcharges, short-notice fees, late-night premiums. None of those are unusual in the industry, but you should know about them at the quoting stage rather than on the invoice.

2. How does billing work?

A receipt per ride is fine for one trip a quarter. It is administrative noise if your executives travel weekly.

What you want is a monthly consolidated invoice with cost centre or project references on each line, so the finance team can allocate without chasing anybody. Ask what terms are offered — net 30 is standard for an established account.

3. Who is driving, and is it the same person?

Named preferred chauffeurs are worth more than they sound. The same person driving your chief executive each month knows which building entrance actually works, which approach to the airport is moving, and that your visiting client does not know the city.

Ask whether chauffeurs are employees or contractors. Ask whether they are licensed and background checked. A legitimate operator answers both without hesitation.

4. Can they produce a certificate of insurance?

If your procurement process requires supplier documentation, this is the first thing to request. A commercial operator will send a COI the same day. If it takes a week or comes with excuses, that tells you what you need to know.

5. What happens when a flight is delayed?

The correct answer involves flight tracking, automatic adjustment, and no additional charge. The wrong answer involves a waiting-time meter starting at the scheduled landing time.

This is the single most common failure in corporate travel, and it is entirely preventable.

6. Who answers the phone at eleven at night?

Dispatch hours matter more than anything on the brochure. A flight diverts, a meeting overruns, a client decides to leave early. If the answer is a voicemail box until nine in the morning, the service is daytime only regardless of what the website says.

Ride-Hailing Versus a Chauffeured Account

Apps are convenient and there is nothing wrong with using them for routine, low-stakes travel. Three things make them unsuitable as the default for business:

Demand pricing. The fare rises exactly when you have least flexibility — weather, convention weeks, delayed evening arrivals. Those are the moments your executive is most likely to be travelling.

No guaranteed vehicle. A booking is a request, not a reservation. Drivers cancel, particularly on early morning airport runs where the return leg is empty. At four in the morning for a six o'clock flight, there is no fallback.

No consolidated billing. Every ride is a separate charge on somebody's card, reconciled by somebody else, with no cost centre attached. For a company running twenty trips a month this is real administrative cost.

The honest counterpoint: for a single employee taking one trip, an app is usually fine and often cheaper. The case for an account is volume, reliability and administration — not luxury.

The Trips Worth Putting on an Account

Executive airport transfers. Predictable, repeated, and the highest cost of failure.

Client collections. Sending a visiting client to find their own ride at an airport they do not know is a small failure of hospitality that costs very little to avoid.

Roadshows and multi-stop days. The vehicle is held for the day, the bags stay in it, and nobody spends the afternoon looking for parking. This is where a chauffeured booking is not close to the alternative.

Convention and conference shuttles. Scheduled loops between the hotel block and the venue. In Indianapolis that usually means the Indiana Convention Center.

Client hospitality. Games, dinners, race weekend. The transport is part of the evening, not an afterthought.

Setting Up an Account

It should take one conversation. A provider needs to know your regular routes, roughly how often you travel, who books, and who gets invoiced. From that they should come back with agreed rates for your routine journeys.

You should not need a minimum spend, a contract term, or a setup fee. If any of those appear, ask why.

Industry accreditation is worth checking if your travel policy requires it. Membership of the Global Business Travel Association and the National Limousine Association is a reasonable baseline.

The Short Version

Fixed price agreed in advance. Monthly consolidated billing. Named chauffeurs who are employees. A certificate of insurance on request. Flight tracking included. And somebody who answers the phone at any hour.

If a provider gives clear answers to those six, the rest is detail.

See our corporate chauffeur service

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