Estimating software for contractors: what it costs and when a spreadsheet wins

What these apps charge a month

The cheap end is genuinely cheap. Joist's Basics plan is $12 a month if you pay month to month, and it caps you at 5 documents a month. Pay for the year and the page shows $8.34 a month. Joist does not name a currency anywhere on the page ¹.

The two best known field service apps cost more, and both state their currency. Jobber's Core plan is $49 a month with one user, and its footnote says all prices are in USD ². Housecall Pro's Basic plan is $79 a month paid monthly, or $59 if you pay for the year, with one user, and its page says prices are in USD and exclude sales tax ⁴.

The price jumps when a second person needs a login. Jobber Connect is $139 a month and includes 5 users ³. Housecall Pro Essentials is $189 a month with 5 users included ⁵. Knowify, which is built more around job costing than around booking, lists Core at $99 a month with one user and names no currency ⁶.

At the free end, Square's Canadian invoices page has a plan with no monthly fee that can send estimates. You pay 2.8% plus 30 cents when an invoice is paid online ⁷. That is worth knowing before you compare anything else, because it sets the floor.

You are paying for the follow-up, not the arithmetic

A spreadsheet already does the math. Your labour rate, your material list, your markup. No app prices a job better than the person who has done the job, and none of these tools knows what your supplier quoted you last week.

What you are buying is what happens after you hand over the number. Jobber describes its quoting tool as professional quotes with customizable templates, signature approvals and automated calendar reminders ⁸. That is the vendor's own copy, but it is an honest list of the parts a spreadsheet does not have: the customer taps approve on a phone, and something nudges you when nobody has replied.

You are also buying a way to take a card. Housecall Pro says its card processing runs as low as 2.59%, with a 1% fee on bank payments ⁴. Square charges 2.8% plus 30 cents on an invoice paid online ⁷. Those percentages are the real price of letting a customer pay on the spot instead of mailing a cheque, and they scale with your revenue while the subscription does not.

The CRA wants certain things on your invoice

An invoice is not just a number with your name on it. The CRA publishes a chart of what has to be on the paperwork you give a customer so they can support a claim ⁹. At a total sale of $500 or more, that includes the buyer's name, a brief description of the work and the terms of payment, on top of your business name, the invoice date, the total and your GST/HST registration number ⁹.

From $100 to $499.99, you still need the registration number and either the GST amount or a clear statement that the total includes it ⁹. Below that the list is short. Most contractor invoices land in the top band, so build the template for that band and stop thinking about it.

A spreadsheet can carry every one of those fields. You only build the template once. The risk with a spreadsheet is not the layout, it is the copy of a copy where one line went missing and nobody noticed for a month.

A proper invoice starts a 28 day clock in Alberta

Under Alberta's prompt payment rules, a project owner must pay the amount payable to a contractor within 28 calendar days of receiving a proper invoice ¹⁰. If the owner wants to dispute it, they have to give notice within 14 calendar days ¹⁰. If you are the one holding the contract, you must pay each subcontractor within 7 calendar days of being paid yourself ¹⁰.

The clock only starts if what you sent counts as a proper invoice. Alberta's list includes your name and business address, the date, the period the work covers, a description of the work, the amount requested, payment terms, who to pay, and a statement indicating that the invoice provided is intended to be a proper invoice ¹¹.

That last line is the one templates miss, in a spreadsheet and in software. No pricing page above promises to add it for you. Check your own template, then add it. It is a one time edit either way.

The sticker price is not what lands on your card

Jobber and Housecall Pro both publish in US dollars ^{2 4}. The Bank of Canada put the US dollar at CA$1.4038 on the day these pages were checked ¹². Your card issuer may add a spread on top of that, and GST goes on the bill.

Then there are seats. Jobber adds users for $29 a month each ². Housecall Pro's page lists $35 a month per additional user ⁵. If everyone in a truck needs a login, count the seats before you compare the headline numbers, because the one user plan is rarely the plan you end up on.

And watch the sign-up price. Jobber's page is running a save up to 40% offer, and the fine print says you must subscribe before October 30, 2026 to get it ². Promotional rates end. Budget for the regular rate, which for Core is $49 a month ².

A spreadsheet is fine at low volume

If you send a few quotes a month, invoice from a saved template and get paid without chasing, you are not the customer these apps are built for. Joist's cheapest plan assumes exactly this kind of volume, with up to 5 documents a month ¹.

Spend an hour making the spreadsheet less fragile instead. One file per job rather than one shared file everyone edits. A number on every quote and every invoice, running in order. Locked cells around the formulas so a thumb on a phone cannot quietly change your markup.

Save the PDF you actually sent, not just the sheet. The sheet shows today's prices. The PDF shows what the customer agreed to, which is the version that matters when someone argues about the total.

Buy the software when the paperwork starts costing you

The signals are about memory, not money. You cannot find the quote a customer approved. The same job gets priced differently depending on who writes it up. Deposits and change orders live in text messages. An invoice went out without the line that makes it a proper invoice, so the 28 day clock never started ¹⁰.

Trial it with real work. Housecall Pro's trial is 14 days free with no credit card ⁴, and Joist offers 14 days as well ¹. Put your next real quotes through it, including an awkward one with a change order and a deposit. Then look at whether customers approved faster, not at whether the quote looked nicer.

Choose the billing term on purpose. The lowest number on every page above is the annual one, and an annual commitment on a tool you have used for a week is a bet. Pay monthly until you know, then switch.

For most contractors, a ready made app is the right answer. Quoting, invoicing and taking a card are the same job in every trade, and a plan at $49 a month buys work nobody should pay to build again ². Custom work earns its keep in one case: when the estimate has to pull from your own price book, equipment list or supplier pricing, or feed a system you already run, and no plan on any pricing page will touch it.