Winter breaks the normal billing cycle
Most trades bill when the work is done. Snow does not cooperate with that. The work happens overnight and on no notice, the same site might get cleared four times in a week and then not once for eighteen days, and the person who did it is a plow operator in a truck at four in the morning, not an estimator with a laptop.
The result, for a lot of contractors, is a shoebox winter: pushes recorded on a phone notes app or a scrap of paper, reconciled against the weather in April, with a percentage of the season's revenue quietly lost because nobody wrote down the 2am salt run on the 14th. The fix is not complicated software. It is making it fast enough to log a completed site from a truck cab in a couple of taps that it actually gets done.
The three billing models, and mixing them
Winter maintenance contracts usually fall into one of three shapes, and most established contractors run all three at once:
- Per push — a fixed price per clearing event, sometimes banded by snowfall depth. Simple to price, but it lives or dies on whether every push actually gets recorded.
- Seasonal flat rate — one contract amount, usually invoiced in monthly instalments from November to April. Predictable for both sides; you carry the weather risk.
- Time and materials — hourly equipment rates plus salt or sand by the tonne. Common on large commercial lots where the scope genuinely varies.
In CrewQuote each of these is just a differently-shaped template. A per-push residential driveway is a two-line template loaded in one tap. A commercial lot on T&M is a template with equipment hours and material lines the operator fills in. A seasonal contract is a recurring invoice at a fixed amount. Nothing forces you to run every client the same way.
The record that matters in March
Slip-and-fall claims arrive long after the snow has gone, and the question is always the same: was the lot cleared, when, and was it salted. A contractor who can produce a completion time and a photo of a cleared lot is in a very different conversation than one working from memory.
Every job in CrewQuote carries its completion timestamp and any photos the crew uploaded against it. That is a genuinely useful contemporaneous record. To be clear about what it is not: CrewQuote is invoicing and quoting software, not a liability or risk-management product, and it does not make any guarantee about what will satisfy an insurer or a court. Ask your insurer what documentation they expect, then make sure your crews are capturing it.
Getting the crew to actually log it
This is the whole problem. Any system a tired operator finds fiddly at 3am is a system that gets skipped, and a skipped push is unbilled revenue.
Crew-level accounts open straight onto the day's route. Each site is a card: mark it done, add a photo, add a note if something was blocked. They do not see pricing, margins or the client list — just the sites and the sequence. Where there is no signal, and in an industrial park at 3am there frequently is not, the update is held on the phone and uploads later without anyone needing to remember to retry.
Reconciling the month
At month end the calendar view shows every job that ran, by day, so you can check it against the weather before invoicing. Pushes roll into invoices, invoices export as CSV in the format QuickBooks and Wave import, and HST applies automatically at whatever rate you have set in your business profile.