Pricing

Plans for owner-ops, company drivers, and small fleets.

Priced so one caught shortpay or one collected detention claim can cover the month.

What this replaces

A bookkeeper runs $200–400 a month — and you’re still the one digging up every doc they ask for, all year long.

Here you snap it once and it’s filed. Your books stay current every day, and at tax time you share it all with your tax person once — one link, done.

Already have a factoring portal?

Keep it — it moves your money. It only sees the loads that run through that one factor.

We run the books across every broker you haul for: real cost per mile, settlement audits, tax-ready exports, IFTA-ready numbers.

See the full comparison — bookkeeper vs. cheap app vs. factoring portal →

Pricing that pays for itself. Immediately.

One shortpay you catch, one detention claim you collect, one late filing you dodge — any one of them can cover the month. Then it just keeps working.

The computer does the paperwork. You keep the wheel.

Same price, same product — cards below show the features that actually apply to you.

Starter

Run your books like a pro.

Free for 30 days

then $2.63/day

$79/mo · cancel anytime

Everything you need to run your whole back office.

Snap a pic of your settlement, we read it — 60 documents a month included, then 30¢ each
Reads settlements, rate cons, BOLs, 1099s, fuel receipts — just snap a pic
Track every load, no limit
Bill the broker in one tap
Real CPM, miles, and take-home updated daily
IFTA done for you — export CSV at quarter-end
CDL, medcard, and permit alerts at 60/30/7 days
Settlement breakdown: deductions, fuel tax, advances, fund balances

Start your 30-day free trial

Pro

See the full rate picture on your loads — it's your right under federal law (49 CFR §371.3).

Free for 30 days

then $4.97/day

$149/mo · cancel anytime

Every load audited, every broker scored.

Everything in Starter, plus:
Settlement audit — flags wrong CPM, duplicate charges, missing detention payFlagship
See what the broker got paid vs. what you got (49 CFR 371.3)
Grade every load A–F before you say yes
Know the real market rate on any lane
Drafts the demand letter when detention goes unpaid
Broker score 0–100 and how fast they actually pay
Bank balance 7, 14, 30, 60, 90 days out
Warns when your CPM drops or miles fall off before it hurts
Catches when a fuel charge gets counted twice
Forward any rate con to your OverTheRoad.AI email — we log the load
Monday morning: one message with how last week really went

Start your 30-day free trial

Fleet

Small fleets. Every truck, every driver, one clean back office.

$249/mo

Up to 3 trucks included · ~$83/truck

Trucks

3 included · $99/mo each after

30-day money-back guarantee · cancel in one click

Running 10+ trucks? Talk to us.

Everything in Pro
Every truck includes its driver's login
2 office seats included (dispatcher, bookkeeper)
Role-based access: Owner · Dispatcher · Bookkeeper · Driver
Per-truck & per-driver P&L + fleet dashboards
Fleet-wide IFTA with per-vehicle filter
1099-NEC generation for contractors
Priority support — 24hr response

Start your Fleet plan

marks a Pro-only feature.·Cancel anytime — no questions asked.

Compare every feature

Every plan, line-by-line.

No asterisks, no “contact sales” gaps. What you see is what ships with each plan.

Feature	Starter $79/mo ≈ $2.63/day	Pro $149/mo ≈ $5/day	Fleet from $249/mo ≈ $89/truck at 5
Document automation
AI document scans per month Settlements, rate cons, BOLs, 1099s, fuel receipts — 14 doc types.	60	250	Unlimited
Forward rate-con email → auto-load Your own @mail.overtheroad.ai address. Replies thread back.
Bill broker in one tap PDF invoice with BOL attached, sent from your carrier identity.
Load + broker intel
Real CPM + take-home, updated daily
A–F load grading before you book Market rate, fuel, deadhead, broker history — factored in.
Live market rates by lane
Broker pay-speed score (0–100) How fast each broker actually pays — not how fast they say.
Money recovery
§371.3 broker transparency letter Auto-generated. No other back-office tool does this.
Detention demand letters BOL timestamps cited. Filed from your carrier identity.
Settlement accuracy audit Flags wrong CPM, missing pay, double-counted fuel.
Duplicate fuel-charge detection
Cash flow + reporting
7 / 14 / 30 / 60 / 90-day cash forecast
CPM drop + margin-bleed alerts
Monday-morning weekly summary
Tax + compliance
IFTA quarterly export (CSV)
CDL / medcard / permit alerts (60/30/7 days)
1099-NEC generation for contractors
Fleet-wide IFTA with per-vehicle filter
Team + multi-truck
Trucks included	1	1	3 (+$99/truck after)
Role-based access Owner / Bookkeeper / Dispatcher / Driver.
Per-truck + per-driver P&L
Multi-LLC QuickBooks sync
Samsara ELD integration
Full audit log
Support + guarantee
Trial	30 days free	30 days free	30-day money-back
Support response	Standard	Standard	Priority · 24hr
Cancel in one click

Tap a plan to expand its feature list.

Starter$79/mo

Document automation

AI document scans per month60
Forward rate-con email → auto-load
Bill broker in one tap

Load + broker intel

Real CPM + take-home, updated daily

Money recovery

Cash flow + reporting

Tax + compliance

IFTA quarterly export (CSV)
CDL / medcard / permit alerts (60/30/7 days)

Team + multi-truck

Trucks included1

Support + guarantee

Trial30 days free
Support responseStandard
Cancel in one click

Pro$149/mo

Document automation

AI document scans per month250
Forward rate-con email → auto-load
Bill broker in one tap

Load + broker intel

Real CPM + take-home, updated daily
A–F load grading before you book
Live market rates by lane
Broker pay-speed score (0–100)

Money recovery

§371.3 broker transparency letter
Detention demand letters
Settlement accuracy audit
Duplicate fuel-charge detection

Cash flow + reporting

7 / 14 / 30 / 60 / 90-day cash forecast
CPM drop + margin-bleed alerts
Monday-morning weekly summary

Tax + compliance

IFTA quarterly export (CSV)
CDL / medcard / permit alerts (60/30/7 days)

Team + multi-truck

Trucks included1

Support + guarantee

Trial30 days free
Support responseStandard
Cancel in one click

Fleetfrom $249/mo

Document automation

AI document scans per monthUnlimited
Forward rate-con email → auto-load
Bill broker in one tap

Load + broker intel

Real CPM + take-home, updated daily
A–F load grading before you book
Live market rates by lane
Broker pay-speed score (0–100)

Money recovery

§371.3 broker transparency letter
Detention demand letters
Settlement accuracy audit
Duplicate fuel-charge detection

Cash flow + reporting

7 / 14 / 30 / 60 / 90-day cash forecast
CPM drop + margin-bleed alerts
Monday-morning weekly summary

Tax + compliance

IFTA quarterly export (CSV)
CDL / medcard / permit alerts (60/30/7 days)
1099-NEC generation for contractors
Fleet-wide IFTA with per-vehicle filter

Team + multi-truck

Trucks included3 (+$99/truck after)
Role-based access
Per-truck + per-driver P&L
Multi-LLC QuickBooks sync
Samsara ELD integration
Full audit log

Support + guarantee

Trial30-day money-back
Support responsePriority · 24hr
Cancel in one click

Before you sign up

Billing questions, answered straight.

No. You start with no card — the full app for 30 days. At day 30 you add a card to keep going; until then nothing can charge you because there's nothing on file.

Not ready for the trial?

Try a free tool first.

Same numbers our Pro plan crunches automatically — available free, no signup, no card. Run one on your next load and decide whether the trial's worth it.

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