What to check before choosing contractor management software

It's 9 PM. The truck's in the driveway, and you're at the kitchen table with three quotes to write. There's a deposit you forgot to ask for, and a text from 6:40 asking what time you're coming tomorrow. You did good work today. Now you're paying for it with your evening.

That's usually when people start looking at contractor management software. It's an app that carries a job from the first call to getting paid. The lead, the quote, the schedule, the invoice and the payment all sit in one place. For a small trade business, it takes over from the text threads, the notebook on the dash and the spreadsheet you keep meaning to update. (Search the term and you'll also turn up HR software for big firms that hire outside contractors. That's a different thing entirely.)

Before you hand over a card number, run one real job through the free trial on your phone. Quote it from the driveway, take the deposit, keep the photos on the job and bill it in stages. Check the tax line and find the export button. Then read the pricing page slowly. The rest of this post walks you through each step.

Why so much contractor software feels built for someone else

Mostly because it was sold to someone else first. Trades in Canada are overwhelmingly small. Statistics Canada counts 137,833 specialty trade businesses with no employees, and another 61,874 small trade employers with one to four.

The big apps grew up selling to outfits with an office and a dozen trucks. That's where the dispatch board comes from, along with the per-user pricing and the onboarding call before you can send your first quote. For a company that size, it's money well spent. For a two-person crew, it's a pile of screens you pay for and never open.

Then there's time. CFIB's latest Red Tape Report found small businesses spend 735 hours a year complying with regulation. That's before anyone writes a quote. Good software should hand some of those hours back.

How to tell it's time for an app

Most trades don't go looking for an app after a quiet week. They go looking after a week like this one. See how many of these sound familiar:

• A customer texted at 8 PM asking when you're coming, and you had to scroll back to find out.
• A quote went out, nobody answered, and you forgot to follow up.
• You started a job without the deposit because asking felt awkward.
• The before photos are somewhere in a camera roll of 4,000 pictures.
• You did invoices at the kitchen table on Sunday.
• A missed call on the ladder never got called back.

One of those is a rough week. If three of them happen every week, that's how the business runs now, and an app will pay for itself.

Want to see what a tidier quote looks like first? Our free quote generator and invoice generator make both as a PDF, with your province's tax already worked out. You don't need an account.

The Driveway Test

Almost every moment that makes you money, or loses it, happens in the driveway. You've walked the job, the customer's at the door, and you're climbing back into the cab. Whatever you can do from there gets done. Whatever needs a laptop waits until tonight, and sometimes it waits for good.

So we boiled our checklist down to one question, asked ten ways. Can you do it from your phone, in the driveway, before you pull away?

#	The check	Trial test	Red flag
1	Quote before you leave	Time yourself from opening the app to a sent quote	Needs a laptop, or a setup call first
2	Calls and texts land in one place	Call and text your business line from another phone	Nothing shows up unless you type it in
3	Yes and deposit, no download	Approve a quote from a second phone	The customer must make an account
4	Photos stay on the job	Add five photos, then find them a day later	Photos only live in your camera roll
5	Bill a long job in pieces	Invoice half a job, then the rest	You work out the balance yourself
6	Sales tax for your province	Quote a job in your province, check the tax line	You type the rate in by hand
7	The app chases late invoices	Leave a test invoice unpaid past due	You have to remember to send reminders
8	Crew see the job, not your margin	Invite a second phone as crew	Crew can see prices and payments
9	Adding a person doesn't change the bill	Read the pricing page for "per user"	Price climbs with every helper
10	You can leave with your data	Find the export button before you commit	No export, or export by request only

Give an app a point for every pass. We'd want to see eight or more before paying for anything. Screenshot the table and run it on every app you try, ours included.

Tip. Use a job you're actually quoting this week. A made-up job is too easy to get through. A real customer, with a real address and a real deadline, shows you exactly where an app slows you down.

The ten checks, one at a time

1. Can you send a real quote before you leave?

A quote written at the kitchen table at 9 PM goes out a day late. By then the customer may have had two other trades through the door, and one of them got a number to them first.

So time yourself. Open the app in the driveway and see how long it takes to send a quote. Your trade's usual services should already be there, with separate lines for labour and materials, and the customer should get a clean PDF that opens on any phone. If the app wants you to finish setting up on a computer first, you've learned what you need to know.

2. Does every call and text land in one place?

You can't pick up the phone with both hands in a panel. A paper notebook won't remind you who you forgot to call back. An app can, as long as the call actually lands in the app.

Look for a business number that rings on the phone you already carry, with calls, texts and email kept together for each customer. Then call and text your business line from another phone. If nothing shows up until you type it in yourself, your leads are still living in your head. Once those leads turn into booked work, our guide on managing multiple jobs picks up from there.

3. Can the customer say yes and pay a deposit without downloading anything?

Every extra step costs you jobs. Ask a customer to create an account and a few of them just won't bother. Asking for a deposit face to face is awkward too, which is how so many jobs start without one.

Send a test quote to a second phone. It should open from a link, with no app and no password, and the customer should be able to approve it and pay the deposit in a couple of taps. Then follow the money. The deposit should come off the final invoice without you doing the math.

4. Do the photos stay with the job?

Before photos protect you. They show the rot that was already behind the wall before you opened it up. They only help, though, if you can find them six weeks later, when the customer asks why the bill went up.

Add five photos to a test job. Come back the next day and find them from the job itself, without opening your camera roll. Emailing photos to yourself for safekeeping doesn't count.

5. Can you bill a long job in pieces?

A three-week reno can't wait three weeks for the first payment. Billing in stages keeps cash coming in while you're buying materials. Working out what's left by hand at 10 PM is how mistakes sneak in.

Invoice half a test job, then invoice the rest. A good app works out the remaining balance and credits the deposit you already took. Your calculator can stay in the glovebox.

6. Does it get GST, HST, PST and QST right?

Most guides skip this one, because most of them are written for the US. In Canada, the tax on your invoice depends on the province. Ontario and the four Atlantic provinces charge a single HST. B.C., Saskatchewan, Manitoba and Quebec charge GST plus their own provincial tax. And whether that tax lands on labour or only on materials depends on your trade.

Quote a real job in your province and look hard at the tax line. Then look for a tax report you could hand your accountant at filing time. If you have to look up the rate and type it in yourself, every invoice is another chance to get it wrong. Our GST/HST rates page lists the current rate for every province and territory, so you can check an app's numbers against it.

7. Who chases the late invoice, you or the app?

For a lot of trades, asking for money is the worst part of the job. So the reminder never gets sent, and the invoice just sits there getting older.

Leave a test invoice unpaid past its due date and see what happens. You want reminders that go out on their own, plus one screen that shows what's outstanding, what's overdue and what's been collected. You should also be able to mark cash, cheque or e-transfer as paid, so the numbers stay true. For the wording to use at each step, see our payment request scripts.

8. What does your crew see?

The day you hire a helper, a new question comes up. Should they see what you charged and what you made? Most owners would rather they didn't.

Invite a second phone as a crew member. They should see the address, the checklist and the photos for the jobs they're on, and nothing about your prices. While you're in there, look at what crew can do as well as what they can see, so you know how the field side works before your first hire starts.

9. What happens to the price when you add a person?

Plenty of contractor apps charge per user. That's fine while it's just you. Then you hire someone, and the bill creeps up every month.

Search the pricing page for "per user" or "per seat", and check whether the price is in Canadian or US dollars. A US price moves every time the exchange rate does. Then work out what you'd pay with one helper, and again with three.

10. Can you leave with your data?

The day you sign up is the easiest day to ask how you'd leave. Your customer list, your quotes and your job history are the business, and they should come with you wherever you go.

One landscaper put it plainly in a LawnSite thread. They don't want to keep switching apps, because their customers' cards are on file. Find the export button before you commit, and check for contracts or cancellation fees while you're there.

Read the fine print before you sign

The ten checks tell you what an app does. The fine print tells you what it costs to stay. Look for these on the pricing page and in the terms:

• A headline price that only covers one person.
• A long contract. At least one of the biggest field service apps sells noncancelable contracts of 12 to 36 months that renew automatically, according to Workyard's app comparison.
• A price in US dollars, so your costs move with the exchange rate.
• Paid credits, where certain features cost extra each time you use them.
• Card fees and payout timing. Ask what each card payment costs, when the money reaches your bank, and whether they can hold your payouts.
• A setup fee, or a call with a rep before you can send a quote.

Any one of these is fine on its own. Add up a few, though, and the real price ends up well above the number on the front page.

Get the most out of a free trial

Most free trials go the same way. You sign up on a Monday, poke around for ten minutes, and never open the app again. Here's a better plan. Push one real job all the way through, start to finish.

1. Pick a real job you're quoting this week.
2. Add the customer as a lead from your phone, wherever you're standing.
3. Build the quote in the driveway, and time yourself.
4. Send it to your own second phone. Approve it and pay a small deposit.
5. Turn it into a job. Schedule it and add photos.
6. Invoice part of it, then the rest. Check the tax line.
7. Export your data before the trial ends.

Keep a note of every step that sent you looking for a laptop. By the end of the week, that note will tell you whether the app fits the way you work.

How StrikeHoney handles the Driveway Test

We build StrikeHoney for Canadian solo trades and small crews, and it runs from your phone. Here's how it handles each check, so you can line it up against anything else you're trying.

#	The check	In StrikeHoney
1	Quote before you leave	Pick your trade, and your services and quote templates are already there, with lines for labour and materials.
2	Calls and texts land in one place	Your own business number rings on the phone you carry. Calls, texts and email land in one inbox, and a lead that sits too long gets flagged.
3	Yes and deposit, no download	The customer opens a link, with no account and no app. They approve and pay the deposit in one tap, and it comes off the final invoice.
4	Photos stay on the job	Photos and documents live on the job, not in your camera roll.
5	Bill a long job in pieces	Invoice the full job, a percentage or specific lines. We work out the remaining balance for you.
6	Sales tax for your province	GST/HST-aware tax settings, plus a tax report for your accountant.
7	The app chases late invoices	Overdue reminders go out on their own. Outstanding, Overdue and Collected sit on one screen.
8	Crew see the job, not your margin	Crew get a money-free view of just the jobs they're on.
9	Adding a person doesn't change the bill	One price in Canadian dollars, every feature, no per-user fees.
10	You can leave with your data	No lock-in. Cancel from the app, and export everything with one tap.

StrikeHoney is $24/mo CAD on the monthly plan, or $19/mo CAD when you pay for the year. Card payments run through Stripe, with a standard payout in about 3 business days. Every feature is on our features page and every fee is on our pricing page. If you're weighing us against a bigger name, our comparison pages put the two side by side.

Before you pick one

The right app is the one you can run from the driveway. Put one real job through every app you try, score it on the ten checks, and read the pricing page for per-user fees, contract terms, currency and card fees. Go with the one that gets the most done before you pull away, and you'll start getting your evenings back.

If you'd like to run the Driveway Test on us, start your free trial. The first 30 contractors get 90 days free, with no credit card, and you can see what's included first.