OWNER-OPERATOR PAYROLL · LEASE-ONS & SMALL FLEETS

You built the fleet one truck at a time. WageTime runs settlement night.

Percentage splits, chargebacks, and escrow lines on one side; your first W-2 company driver on the other. WageTime is payroll for owner-operator fleets, built to settle both in one Friday run.

Built on infrastructure processing $35B+ in payroll & taxes · 4.3M+ W-2s/1099s filed
SOUND FAMILIAR?

Growing from one truck to five never added an office. It just added Friday nights.

More than nine of every ten US for-hire carriers operate ten trucks or fewer (ATA, 2025), and in a fleet that size the settlement clerk, the payroll department, and the driver of truck number one are usually the same person. The math is not the hard part. The hard part is that the records have to hold up: to your operators, to a lease dispute, and to the first state agency that asks.

THE 15-DAY CLOCK

A federal stopwatch starts at the delivery receipt

Lease a truck onto your authority and federal truth-in-leasing rules (49 CFR 376.12) start timing you: the operator must be paid within 15 days of submitting delivery documents, whether or not the shipper has paid you yet. On percentage deals the operator is also entitled to a copy of the rated freight bill to check the split. Miss either and the argument is no longer with a driver. It’s with a regulation.

THE CHARGEBACK BINDER

Every deduction owes its receipts

Bobtail and physical-damage premiums, occ-acc, trailer rent, plates, a fuel advance pulled as a money code on Tuesday: the lease must list every chargeback, and the operator can demand the documents behind each one. OOIDA has turned sloppy deduction records into federal class actions more than once. If your deduction history lives across six spreadsheets and a fuel-card portal, you cannot produce it.

THE ESCROW LEDGER

Held money is the most audited money

Maintenance escrow sounds simple until a lease ends. The regulation expects an accounting of every transaction in and out, interest on the balance, and the fund returned within 45 days of termination. Arctic Express lost in federal court over exactly this, and the FMCSA’s leasing task force reported in January 2025 that fewer than 1 in 100 lease-purchase drivers ever end up owning the truck. Regulators read held money closely. A shoebox of statements is not an accounting.

THE FIRST-HIRE CLIFF

One W-2 paycheck creates an employer

The day you seat a company driver in truck two, you stop being only a carrier and become an employer: federal withholding and deposits, a state unemployment account, new-hire reporting, and workers’ comp questions your occ-acc certificate never had to answer. None of it waits until you can afford an office manager.

YOUR OWN CHECK COMES LAST

The owner is the payroll department

You also drove 2,600 miles this week. After the operators are settled and the driver’s paycheck clears, whatever is left gets computed at midnight in a spreadsheet only you can read. Every hour of that is unpaid office work stapled to a driving job, 52 times a year.

Here is how WageTime runs both sides of a small fleet’s pay without adding office staff.
01 · THE SETTLEMENT, LINE BY LINE

What does a clean lease-on settlement look like?

In WageTime, a clean settlement reads top to bottom with no mystery: the load’s gross, the operator’s percentage computed through tiered commission structures, the fuel surcharge passed through on its own line, then every deduction named and dated.

  • Per-mile and per-load deals as per-unit pay codes.
  • Named deduction lines: advances, insurance, trailer rent, escrow, configured once per operator.
  • Equipment and asset deductions where state law permits.
  • Landstar comparison: 62-76% of revenue kept, 100% fuel surcharge through (2025 FAQ).
app.wagetime.com/payroll/settlement

Settlement · KD Hauling LLC · Week 30

Percentage pay codeChargebacks itemized
Load gross $6,942.50 · percentage deal, fuel surcharge passed straight through
KD Hauling LLC · lease-on settlement
Linehaul share, 72%$4,998.60
Fuel surcharge, 100%$611.40
Fuel advance, Jul 14-$600.00
Occ-acc, monthly-$152.00
Trailer rent, weekly-$150.00
Escrow, per settlement-$100.00
Net settlement$4,608.00
Settlement recordevery deduction named and dated

Replaces the eleven-column settlement spreadsheet, and the Friday night it eats.

02 · THE PART 376 PAPER TRAIL

Which settlement records do truth-in-leasing rules expect?

Truth-in-leasing rules put five recordkeeping-heavy duties on any carrier that leases on owner-operators, and those duties are yours, not your software’s. What WageTime gives you is the record that survives the argument: every settlement line dated and documented.

  • Pay within 15 days of delivery documents; rated freight bill on percentage deals.
  • Chargebacks listed and provable; escrow accounted with interest, returned within 45 days.
  • Deduction history per operator, exportable, with paperwork on the worker’s record.
  • Full audit logging with effective-dated changes.
  • Scheduled reports: each operator’s deduction history, quarter by quarter, or fleet-wide.
app.wagetime.com/payroll/deduction-history

Deduction History · R. Calloway · Q3 2026

Audit log on1 document missing
$3,214.50Charged back
14Deductions logged
1Document missing
DeductionAmountDocument
Fuel advanceJun 12 · money code$400.00On file
Physical-damage premiumJun 30$214.00On file
Trailer rentJul 7 · weekly chargeback$150.00On file
Escrow contributionJul 7 · per settlement$100.00On file
Plate renewal splitJul 14 · not yet attached$87.50Missing
Every chargeback dated on the operator recordhistory exportable per operator

Replaces the chargeback binder you would have to reconstruct from six logins, after the demand letter arrives.

03 · FROM ONE TRUCK TO AN EMPLOYER

What changes when you hire your first company driver?

One W-2 hire changes your legal shape: federal withholding and deposit schedules, a state unemployment insurance account, new-hire reporting, and a W-2 the following January. WageTime carries that stack from the first paycheck, in the same run that still settles your 1099 lease-ons.

  • Effective-dated tax setup from the first hire’s start date.
  • Every filing and deposit handled automatically, all 50 states plus Puerto Rico.
  • Self-onboarding with e-signatures; W-9 and contractor setup beside it.
  • Year-end W-2s and 1099s both included.
  • Unlimited runs: staying weekly costs nothing extra.
app.wagetime.com/people/first-hire

First Employee Setup · Truck 2 · D. Reyes

Effective-dated setupSUI account registered
Setup stepStatus
Federal withholding and depositsEffective Aug 3Active
Texas unemployment accountEffective Aug 3Registered
New-hire reportFiled Aug 4Filed
Direct deposit and self-onboardingEffective Aug 3Complete
First payroll runScheduled Fri, Aug 7Scheduled
5 of 5 setup steps completeW-2 included at year-end

Replaces the afternoon on hold with the state unemployment office, guessing which registration comes first.

04 · EVERY PAY MODEL IN THE YARD

Can one payroll run lease-ons, company drivers, and the owner?

A five-truck fleet can carry four pay models at once: two lease-ons on percentage, a company driver on cents per mile, a dispatcher on hourly, the owner on salary. WageTime runs the whole yard as one payroll, contractor settlements beside full W-2 tax math.

  • Percentage settlements and W-2 paychecks in the same run.
  • Authority LLC and equipment LLC as separate EINs, one login.
  • QuickBooks posting by department; GL export with segment mapping.
  • Contractor and employee year-end forms from one system.
  • TMS or ELD miles import, no double entry; we’ll confirm the exact flow.
app.wagetime.com/payroll/run-register

Pay Run · Week 30 · Whole Yard

Four pay models, one run2 EINs, one login
KD Hauling LLC1099 lease-on$4,608.00
settlement $4,608.00 · 72% linehaulno withholding
R. Calloway1099 lease-on$3,187.25
settlement $3,187.25 · per-mile dealno withholding
D. ReyesW-2 driver$1,014.32
gross $1,306.80 · $0.54/mitaxes withheld
M. VanceW-2 owner$1,148.87
gross $1,500.00 · owner salarytaxes withheld
This run$10,602.05taxes and filings automatic

Replaces three tools pretending to be one payroll, and the January reconciliation between them.

PRICING

Simple payroll pricing. No surprises.

Full-service payroll is $10 a month per person paid that month, plus $50 a month per company, with unlimited runs. No long-term contracts, no per-run charges.

  • Full-service payroll, unlimited runs
  • Federal, state & local tax filing
  • Year-end W-2s & 1099s
  • Direct deposit, checks & pay cards
  • Contractor payments & filings
  • Off-cycle runs & bonuses, no extra fee
  • Employee paystubs & W-2 access
  • QuickBooks integration
$10/mo per person paid
+ $50/mo per company

Off-cycle runs and bonuses cost nothing extra. No long-term contracts; cancel anytime.

Example: 50 people paid × $10 + $50 company = $550 for the month

HR & hiring, onboarding, PTO, time tracking, benefits, and workers’ comp are optional add-ons, priced separately when you’re ready.

See a demo
THE INFRASTRUCTURE BEHIND WAGETIME
$35B+
in payroll & taxes paid
2.8M+
employees paid
4.3M+
W-2s & 1099s filed
100%
of tax filings automated

Owner-operator fleet payroll FAQ

How do I pay owner-operators leased to my authority?

Most lease-on agreements pay a percentage of linehaul revenue or a flat rate per mile, with the fuel surcharge passed through to the operator. In WageTime, percentage splits run through tiered commission structures and mileage deals run as per-unit pay codes, with advances, insurance chargebacks, trailer rent, and escrow contributions itemized on every settlement.

When do I have to pay a lease-on operator after a delivery?

Federal truth-in-leasing rules require payment within 15 days after the operator submits delivery documents, whether or not you have been paid for the load. Percentage deals also entitle the operator to a copy of the rated freight bill. Those duties sit with you as the carrier; WageTime keeps every settlement dated and itemized so the record exists when someone asks.

Do my 1099 owner-operators need workers’ comp?

Whether 1099 owner-operators need workers’ comp is a call for you and your insurance agent: some states require coverage for any employee, others exempt true independent contractors. Many lease-on fleets carry occupational accident insurance for 1099 operators instead; third-party guides put typical premiums between $600 and $2,400 a year as of 2026. In payroll, the occ-acc chargeback shows as a named deduction line.

Should my drivers be 1099 or W-2 as the fleet grows?

Classification is a decision for you and your attorney, and the federal test keeps moving: the DOL paused enforcement of its 2024 independent-contractor rule in May 2025 and proposed rescinding it in February 2026, while some states apply stricter tests. WageTime keeps both models runnable: contractors and employees in one payroll, 1099s and W-2s both included at year-end.

Can I run per diem for my owner-operators?

Not for the 1099 side: self-employed owner-operators claim per diem on their own tax returns, substantiated by their trip logs, and a carrier does not run it for them. A payroll per diem program applies to W-2 company drivers, where it runs as its own earning line configurable as a non-taxable type. You design that program with your tax advisor.

What does payroll cost for a three-truck owner-operator fleet?

The company pays $50 a month, then $10 for every person who actually gets paid that month, contractor or employee. An owner paycheck, one company driver, and two lease-on operators comes to $90 in a month when everyone is paid. Runs are unlimited, so weekly settlements and an off-cycle bonus cost nothing extra.

Bring one settlement statement.

Your last settlement sheet, the lease’s deduction list, and a headcount. In twenty minutes on a live demo company, a payroll specialist will build a percentage settlement with your deduction lines, run a W-2 paycheck beside it, and show you the statement your operators would see.

Book a 20-minute demo