Back to Corporate Accounts
Free Guide for Corporate Travel Managers

5 Questions to Ask Before Signing Any Chauffeur Vendor

Most corporate ground transport vendors look the same on a rate card. The difference shows up in the insurance clause, the driver classification, and what happens at 2am when a flight gets delayed. Here are the 5 questions most EAs and travel managers don't think to ask — and why they matter.

10 min read•Updated April 2026

The 5 Questions

  1. 1.What's your commercial auto insurance coverage limit?
  2. 2.Are your drivers W-2 employees or 1099 independent contractors?
  3. 3.What's your policy for flight delays, especially after midnight?
  4. 4.Do you offer NET-30 invoicing with ride-level cost codes?
  5. 5.What's your backup plan if the primary vehicle breaks down?
Question 1

What's your commercial auto insurance coverage limit?

Why it matters

If a vendor carries only the state minimum ($250K–$500K), your executive is riding underinsured. In a serious incident, your company can be named in the lawsuit — the vendor's policy exhausts fast, and plaintiffs come after the corporate client next.

What to ask for

A current Certificate of Insurance (COI) showing minimum $1.5M combined single-limit commercial auto liability, plus $1M umbrella. Ask them to name your company as an additional insured on rides booked under your corporate account.

Red flag

Vendor hesitates, says "we'll send it later," or sends an expired COI.

Green flag

Vendor sends a current COI within 24 hours and has umbrella coverage in writing.

Question 2

Are your drivers W-2 employees or 1099 independent contractors?

Why it matters

Post-2020 case law has shifted liability in rideshare and limo incidents. W-2 drivers = vendor is clearly responsible. 1099 drivers = grey zone; in a claim, the vendor's lawyers may argue "the driver was an independent contractor" and your company gets dragged into litigation to establish the chain of liability.

What to ask for

Prefer vendors with W-2 drivers under commercial livery license. If they use 1099s, confirm each driver carries individual commercial policies and the vendor has a written indemnification clause in your service agreement.

Red flag

Vendor calls their drivers "partners" or "contractors" and can't produce proof of individual commercial insurance.

Green flag

W-2 drivers with vendor-carried commercial insurance, or 1099 drivers with individual commercial policies verified yearly.

Question 3

What's your policy for flight delays, especially after midnight?

Why it matters

ORD cancellations and delays happen constantly. If your CEO's 11pm flight becomes a 2am arrival, a good vendor tracks the flight, adjusts pickup automatically, and doesn't charge overage fees. A bad vendor either doesn't show up or bills you 3× for "waiting time."

What to ask for

Written flight-tracking policy: free pickup-time adjustment for any delay caused by the airline, and capped waiting time fees (e.g., first 60 min free, then flat $40/hour — not $20 per 15-min block).

Red flag

Vendor says "we charge standard waiting-time fees" without a flight-delay exception.

Green flag

Vendor integrates with FlightAware or similar, adjusts pickup auto-magically, and has a flight-delay grace policy in writing.

Question 4

Do you offer NET-30 invoicing with ride-level cost codes?

Why it matters

Per-trip credit card charges create AP nightmares for finance teams: reconciling 40 small charges, matching to expense reports, handling personal vs. client-billable rides. NET-30 consolidated invoicing with cost codes turns 40 charges into 1 monthly statement your AP team actually enjoys.

What to ask for

Monthly invoice with: passenger name, pickup/drop-off location, date/time, cost center or project code, rate breakdown (base + tolls + tip), and the ability to split rides across multiple cost codes.

Red flag

Vendor only accepts credit card per trip, or sends PDFs without ride-level detail.

Green flag

Vendor provides a portal + monthly invoice with cost codes and exports to CSV/Excel for easy upload to your ERP.

Question 5

What's your backup plan if the primary vehicle breaks down?

Why it matters

A CEO stuck on the Kennedy Expressway with a broken-down Suburban is a fireable event for whoever booked the ride. Small operators with 1–2 vehicles cannot credibly answer this. Without backup capacity, one mechanical issue means a missed flight, a missed board meeting, or worse.

What to ask for

Ask: "What happens if the vehicle assigned to my CEO breaks down 20 minutes before pickup?" A real answer names specifics: backup vehicle dispatched in 10-15 min, affiliate partnership with [named network] for overflow, or sister-operator mutual aid agreement.

Red flag

Vendor says "we've never had that happen" or gives a vague reassurance.

Green flag

Vendor cites affiliate network partnerships (Blacklane, WindyCity, Carey, etc.), has a minimum fleet size of 5+ vehicles, and can put the backup policy in your service agreement.

Bonus: The 3-email RFP sequence for switching vendors

When you're ready to put your current vendor on notice or shortlist new ones, use this simple 3-email template:

Email 1 — Current Vendor

"We're reviewing our ground transportation contract. Please send: current COI with limits, driver classification (W-2 / 1099), monthly invoicing sample, and flight-delay policy. Need these by [date]."

Email 2 — Shortlist (3 vendors)

"We're evaluating Chicago ground transportation vendors for [company name], ~[volume] rides/month. Please provide: rate card, COI, reference contacts at 2 comparable accounts, and a sample monthly invoice."

Email 3 — Finalist

"We'd like to proceed pending: (1) backup-vehicle policy in writing, (2) named-insured status on COI, (3) 30-day termination clause. Please send the revised agreement for legal review."

Save This for Later

Get the printable PDF version

Share it with your team or keep it on file for your next vendor review. We'll email it right over — no spam, ever.

By requesting, you agree to receive the guide by email. No marketing follow-up unless you ask.

Curious how Exclusive Drive answers these 5 questions?

We built our corporate program specifically to pass this checklist — $1.5M insurance, W-2 drivers, affiliate backup network, and NET-30 ride-level invoicing.

Request a Corporate AccountAsk a Question
Need a ride? Chat with us