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Pricing

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

Priced so one shortpay you catch, or one detention claim that gets paid, 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 checks, tax-time exports, IFTA estimates.

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

Simple monthly pricing.

Every plan is the whole back office. Month to month — cancel anytime.

The computer does the paperwork. You keep the wheel.

Same price, same product — the cards show what applies to you.

Starter

Run your books like a pro.

$79/mo

10% off your first month

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 miles and gallons by state, estimated as you go — export at quarter-end
  • CDL, medcard, and permit alerts at 60/30/7 days
  • Settlement breakdown: deductions, fuel tax, advances, fund balances
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Recommended

Pro

Every settlement checked, every broker's payment history in one place.

$149/mo

10% off your first month

Every settlement checked against its rate con.

  • Everything in Starter, plus:
  • Settlement check — flags possible wrong CPM, duplicate charges, missing detention payFlagship
  • Request the broker's records on your loads (49 CFR 371.3) — letter drafted for you
  • Load profit check: rate after fuel and deadhead, before you book
  • Compare a rate to the market average for the region
  • Drafts the detention request when detention goes unpaid
  • Broker days-to-pay and payment history from your loads
  • Bank balance 7, 14, 30, 60, 90 days out
  • Warns when your CPM drops or miles fall off before it hurts
  • Flags fuel charges that look 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
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Fleet

One place for every truck's loads, paperwork and money.

$249/mo

3 trucks included, +$99 per truck

10% off your first month

How many trucks?

3

Included in the base price

Running more than 10 trucks? Talk to us.

  • Everything in Pro, for every truck
  • Driver app: their loads, snaps and directions
  • Roles: Owner, Dispatcher, Bookkeeper, Driver + a free read-only Accountant
  • Logins are free. Drivers only see money if you allow it
  • Live map when drivers share their trip (their choice)
  • Driver pay summaries you approve first
  • Expiry reminders for CDLs, med cards and truck papers
  • P&L estimate from your data, per truck and driver
  • One-click export of everything
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See Fleet

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

Compare every feature

Every plan, line-by-line.

What you see is what ships with each plan.

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 + billing

      • Trial10% off
      • 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
      • Market rate comparison (regional averages)
      • Broker pay-speed score (0–100)

      Money recovery

      • §371.3 broker transparency letter
      • Detention request letters
      • Settlement check
      • 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 + billing

      • Trial10% off
      • Support responseStandard
      • Cancel in one click
      Fleet$249/mo

      Document automation

      • AI document scans per month500
      • 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
      • Market rate comparison (regional averages)
      • Broker pay-speed score (0–100)

      Money recovery

      • §371.3 broker transparency letter
      • Detention request letters
      • Settlement check
      • 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 per truck)
      • Role-based access
      • Driver app + pay summaries you approve
      • Live map (driver shares their trip)
      • P&L estimate from your data, per truck + driver
      • Full audit log

      Support + billing

      • Trial10% off
      • Support responsePriority · 24hr
      • Cancel in one click

      Common questions

      Straight answers. Tap a question.

      When will I be charged?

      Your 10% discount is applied at checkout, so your first month is billed today at the reduced rate — there's no 30-day trial on a referral signup. Cancel anytime in one click; your data is never deleted.

      Can I cancel anytime?

      Yes. Cancel from your settings in one click — no phone calls, no exit survey. You keep access through the end of the period you already paid for. Month to month, no contracts.

      I'm leased to a carrier, not running my own authority — does this work for me?

      Yes. Snap your weekly settlement and we break down every deduction (fuel, escrow, advances, occ/acc, plates) and flag things like double-billed fuel or a rate that doesn't match. You see your take-home per mile (not just the gross on top), track receipts and out-of-pocket expenses for your 1099/Schedule C, get CDL/med card/permit reminders at 60/30/7 days, and see the carriers you run under side by side. Invoicing, IFTA, and broker tools are hidden for you because your carrier handles those.

      My factoring company already gives me free software. Why pay for this?

      Keep the portal — it's how you get paid fast. But it only sees the loads that run through that one factor. OverTheRoad.AI puts the brokers and loads you upload into one place and turns your paperwork into the numbers that run the business: your cost per mile, a check on every settlement, tax exports organized by Schedule C line, and IFTA estimates for your quarterly return — all based on what you upload. The portal moves your money. This runs your books.

      Does it work on my phone?

      Yes — it's built for the phone first. It works in any browser, and you can add it to your home screen so it opens like an app. Snap documents with your camera, log loads, and send invoices from the cab. No laptop needed.

      Is my data safe?

      The only financial data we hold is what you upload or forward us — settlements, invoices, fuel receipts. It's encrypted in transit and at rest, your account is walled off from every other user, and payments run through Stripe so we never see your full card number. You can export or delete your data anytime, and we don't sell your personal information.

      How long does setup take?

      Pick your situation (leased, own authority, lease-purchase, and so on) and we hide what doesn't apply. If you have a DOT number we pull your carrier info. Snap a rate con or forward one to your OverTheRoad.AI email and your first load is logged.

      How do you handle my 1099 income vs. a Schedule C filer?

      Both work. At signup you pick your situation and the Tax page adapts. If you're leased, gross income comes from your settlements and we line it up against the 1099-NEC each carrier sends in January. If you run your own authority, gross income comes from paid invoices. Either way you get Schedule C deductions tracked all year, quarterly tax estimates, per diem from load dates, and a share link for your tax preparer. Every number is an estimate based on what you've uploaded.

      Can I compare the carriers I run under?

      Yes. Every settlement you scan is tagged with the carrier, so over time you see them side by side — pay per mile, deductions per mile, days to pay, and net take-home — based on the settlements you've uploaded.

      Does OverTheRoad.AI replace QuickBooks?

      It handles the trucking side QuickBooks doesn't: IFTA estimates (if you have your own authority), load profit, settlement breakdowns, broker or carrier payment tracking, compliance reminders, and fuel card imports. If you keep QuickBooks, our CSV/PDF exports drop right in.

      Why does this cost more than a $19 trucking app?

      Because it replaces a different line item. A bookkeeper runs $200–400 a month, and every time they need something, you're the one hunting down settlements, receipts, and numbers. Here everything lives in one place the moment you snap it. The books stay current daily, your tax and IFTA estimates are ready every quarter, and when your tax person needs it, you share it once.

      What payment methods do you accept?

      Major credit and debit cards (Visa, Mastercard, Amex, Discover). Stripe handles billing — your card details never touch our servers.

      What happens if I go over my document-scan limit?

      Nothing sudden — no plan cuts you off mid-month. Every plan includes a monthly scan budget (Starter 60, Pro 250, Fleet 500). Past it, extra scans are $0.30 each, and you approve that before a single extra scan is billed.

      Annual vs monthly — what's the difference?

      Annual saves you two months on Starter, Pro and Fleet (extra Fleet trucks are $990 a year instead of $99 a month). Same features, same cancel-anytime policy — you pay once a year.

      Is there a free trial on Fleet?

      Yes. Fleet starts with the same free 30-day trial, no card needed — add your trucks and invite your drivers. When the trial ends without a card, the office tools go read-only — drivers keep the free map and can still snap, and nothing is deleted. Add a card any time to pick up where you left off. Questions about billing? See our Refund Policy.

      Can I upgrade or downgrade later?

      Yes, either direction, any time. Upgrades take effect right away and are prorated. To downgrade or change billing interval, email support@overtheroad.ai and we'll switch it for you.

      How does Fleet pricing work as I add trucks?

      Fleet includes 3 trucks. Each truck after that adds $99/mo ($990/yr on yearly billing). Logins are free — drivers, dispatcher, bookkeeper and a read-only accountant never cost extra. Trailers don't count. Your bill is based on the most trucks you had in the billing period; remove one and your next bill goes down. Running more than 10 trucks? Email support@overtheroad.ai.

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