The leaves are turning, mowing season is winding down, and winter still feels far off to a lot of people – but not to the operators who win next season. They're not waiting for the first forecast to start moving; they built their plans months ago. Whether you self-perform your routes or manage a portfolio of properties, what's locked in – and what still isn't – decides how smooth (or chaotic) this winter looks.
If you want to be that top-performing company, this is what you should have already done and be doing now:
If you're not already, you should treat your snow season like a 52-week business, not a seasonal scramble. That means planning sales and staffing at least six months out and targeting Sept. 1 as your contract finalization deadline. If you're still negotiating new business, you're compressing the time in which you must hire, train and line up subcontractors; and a contract signed with less than 60 working days of lead time should be evaluated carefully, not rushed.
For management companies: If contracts aren't finalized, push for it this week. Every day it slips pushes your contractor's staffing and equipment planning later, and that risk lands back on your properties. Remember, you still need to source reliable and ready contractors to do the work, and they need the time to be able to prepare, as well.
Contracts get signed on paper, but winter gets fought on the pavement, and too many disputes trace back to a site nobody actually walked before the season. Top-performing companies are scheduling preseason walk-throughs now: mapping salt zones, confirming gate codes and access points, flagging drainage issues and hardscape damage from last winter, and setting a shared understanding with the property manager of what "serviced" looks like. Do this in September and October, not the morning after the first storm.
Ambiguity in a snow contract is a lawsuit waiting to happen. Response thresholds, scope, geographic boundaries and billing terms need to be nailed down before the first flake falls, not negotiated mid-storm. The industry still doesn't have a universal standard for when plowing or salting should trigger, which means your contract must spell it out, or you're exposed.
This is also where weather and dispatch technology earns its keep – hyperlocal forecasting and automated dispatch tools are quickly becoming the difference between crews that respond on time and crews that find out too late.
Labor is still the tightest bottleneck in this trade. Skilled operators are harder to keep than to find, and the companies that retain crews are moving to year-round employment models and investing in equipment that lets one operator cover more properties and square feet of pavement with less fatigue. Sectional pushers, high-flow hydraulics and precision spreaders are just a few ways to combat speed and total square feet covered with less equipment. If you're still planning to run more trucks with more part-time drivers to solve capacity, that's a 2015 answer to a 2027 problem.
Parts, spreaders and plows are taking longer to source, and salt supply keeps tightening every season the market grows. Waiting until October to order is how you end up short in January. Lock in suppliers, calibrate equipment, and get salt contracts signed this summer, not right before the first storm.
Commercial liability costs for snow keep climbing. One facilities study put average increases north of 6% a year, with insurance now ranked alongside labor and equipment as a top-three cost driver. Most commercial and property management contracts now require $1 million to $2 million in coverage with a specific snow/ice endorsement before they'll even sign. Credentials like SIMA's Advanced Snow Manager and Certified Snow Professional have measurably helped members defend claims and hold premiums down, along with weather monitoring systems and forecasts specific to their service areas. If you're not documenting to that standard, your renewal will hurt more than it needs to.
Timestamps, GPS breadcrumbs and photos on every route are now the baseline defense against slip-and-fall claims, not an upgrade or a premium add-on for removing snow. GPS tracking is already used by 72% of commercial fleets for routing and accountability. If your crews aren't documenting every push and every application, you're carrying risk you don't have to. Invest in the proper technology to show the work you do is done properly and correctly.
Winter 2027 isn't a season away; it's a to-do list sitting on your desk right now. Contracts, staffing, equipment, salt, insurance and documentation all get harder and more expensive the longer you wait. The companies that treat summer as game-planning season are the ones still standing and profitable after the last storm melts.
If you're a management company, your to-do list looks the same: audit your contractor's insurance certificates, make sure you know how they document proof of service, and get the site walk on the calendar before you sign off on the season.
If you don't already think snow 52 weeks out of the year, start now! Your January self will thank you.
JP Sanieski, CSP, ASM is director of commercial accounts for Perrone Landscaping. Email him at jp@perronelandscaping.com.