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Contractor invoicing software: what a year costs at 20 and 50 invoices
Square, Joist, FreshBooks and Jobber, priced for a contractor who sends quotes and invoices and takes payment online. Start with how many invoices and clients you need the plan to hold, then look at the card rate.
By card at 20 $500 invoices a month, Jobber Core cost $3,900 a year, Square Free $4,032, FreshBooks Plus $4,068, Square Plus $4,140 and Joist Pro $4,510.
Card fees are $3,552 to $4,306 of that, so the card rate moves the total more than the plan. Square Free and Plus tie at 294 card invoices of $500 a year; Plus is cheaper from the 295th. At 20 invoices a month (240 a year) Free is $108 cheaper than Plus. Paid by bank transfer, Square Free is cheapest at $1,200. The totals assume $500 invoices, one location and list prices, so replace that with your own average.
Where a year of invoicing costs goes
Dark is the subscription, light is payment fees.
A year at 20 invoices a month ($500 each), all paid by card
Worthd arithmetic: subscription at monthly list price times 12 (Jobber Core at its annual-billing price), plus the fee per $500 invoice times 240 invoices.
Yearly totals at 20 and 50 invoices a month
The same five plans at both volumes, by card and by bank transfer. At 50 a month Jobber Core is still $240 a year below Square Plus, because both charge 2.9% + 30c.
Each plan shows four yearly totals.
Subscription plus payment fees for a year, on $500 invoices, cheapest first by card at 20 a month.
FreshBooks Lite ($23) would total $3,828 at 20 card invoices, but it covers 5 billable clients. FreshBooks lists an 80% off for 4 months promotion with no end date, so these totals use list price. Joist Basic is left out because it allows 5 documents a month.
The limits that decide the plan
Invoice, document and client caps, and how many people a plan covers, are as the vendors print them. A plan that caps you before your volume costs more than its price suggests.
Each plan shows price, what caps it, and users.
Plan limits as the vendors print them, US dollars before tax.
From $5.99 a month; plan prices are not readable on the page
Starter 30 invoices a year, Professional 100, Premium unlimited
Unlimited team members on all plans
Square is priced per location. Square's help article on its new subscription plans says the older separate Invoices subscriptions are legacy and that moving to the new plans cannot be undone, so an older Square Invoices price may differ from the one here; new buyers see Free, Plus and Premium.
Joist charges up to 3.49% + 49c and lists no free plan; its Basic plan covers 5 documents a month, so a contractor sending 20 invoices a month needs Pro or above.
2go (Invoice2go) Starter allows 30 invoices a year, so at 20 a month only its unlimited plan fits, and that plan's price is not readable on the page.
Payment fee on one invoice
Card rates for an online invoice and the bank-transfer fee, with the cost of one $500 invoice. All Joist fee examples on this page use the US Joist Payments with Stripe schedule.
Online invoice card rate, and what one $500 invoice costs by card. ACH is $5.00 on all five at $500.
Quotes and invoices only, clients pay by bank transfer:Square Free, $1,200 a year at 20 invoices.
Clients pay by card, under about 294 invoices a year:Square Free beats Square Plus, and Jobber Core beats both at 240 invoices ($3,900), if one user is enough and you also want the scheduling Jobber lists in Core.
Bookkeeping and expenses with invoices:FreshBooks, which caps billable clients at 5, 50 or unlimited by plan and charges $11 a month for each extra team member.
Many documents and clients, one price:Joist Pro at $17 a month, with the highest card rate here.
What changes if my average invoice is $2,000 instead of $500?
Card fees scale with the invoice, bank-transfer caps start to matter. At $2,000 one card payment costs $58.30 at 2.9% + 30c, $66.30 at Square Free, $70.29 at Joist. By bank transfer 1% is $20 on Jobber, FreshBooks and Square Free, but $15 on Joist and $10 on Square Plus because of their caps. Worthd arithmetic from the rates in the table above.
Do these totals include Jobber's new-customer discount?
No. They use list prices. Jobber's pricing page showed a new-customer offer ("Save up to 40%") for plans bought before Oct 30, 2026, 11:59 p.m. PT, checked Oct 21; it is not in these totals and does not apply to existing customers.
What do keyed-in cards and cards on file cost?
Square lists 3.5% + 15c on all three plans for a card entered by hand or kept on file, which is $17.65 on a $500 invoice. The other tools here print one online card rate, so ask each vendor how a keyed card is charged before you rely on the table.
US list prices before sales tax. Square's pages did not print their prices in the text our checker could read, so the Square figures come from a browser read on Oct 23 and may change. Totals are Worthd arithmetic on a $500 invoice. Report a correction.
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