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Straight answers
The questions people ask most about starting and running a roofing business in Ontario. Answered straight, with links to the official sources.
Yes — it's probably the most physically punishing of the common trades: heat on the roof in summer, cold in the shoulder seasons, height, and carrying bundles up a ladder all day. It pays for that, and people do it for years, but everyone should treat it as a trade you build a way out of — into sales, estimating, or ownership — not one you do at 60.
Residential (shingles) is the easy entry: lower barrier, homeowner customers, storm-season volume, faster jobs. Commercial (flat/membrane) has a real barrier — manufacturer certification and torch-safety training — but higher margins, property-manager clients, and recurring maintenance contracts. Residential is where you start; commercial is where the steadier, bigger business often lives.
Roofing is seasonal in Ontario — the busy stretch is roughly spring through late fall, and deep winter is slow for installs. Operators handle it by stacking work in season, doing repairs and emergency leak calls in winter, pairing with a winter trade or snow removal, or running commercial (which has more year-round service work). Plan the cash-flow gap before your first winter.
It can be very lucrative — a hail or wind event creates a wave of insurance-funded replacements — but it's a different business: heavy on sales, adjuster relationships, and supplements, and the segment has enough bad actors that your reputation is everything. Done honestly it's a strong model; done sloppily it's how roofers get a bad name (and chargebacks).
Fast on paper — no trade licence, modest equipment — but roofing rewards experience because mistakes leak and fail publicly. Many start a residential shingle business after a few seasons leading crews. Commercial takes longer because you need manufacturer certification. The real constraints are WSIB (roofing carries high rates), insurance, and a reputation for not leaving leaks.
For the work, yes — experienced roofers earn solid hourly money, and roofing business owners do well ($85k–200k+ depending on residential vs commercial). The trade-off is the body and the seasonality. Roofing pays a premium precisely because it's hard and a lot of people won't do it — which also means there's steady demand for those who will.
No provincial trade licence — roofer is non-compulsory. You do need a municipal business licence, WSIB, insurance, and — critically — Working at Heights training for every worker on a roof, which is mandatory under the Occupational Health and Safety Act.
Roofing has a low licensing barrier but real equipment costs: ladders/lifts, safety gear, a truck/trailer, and tear-off disposal. Add incorporation (~$400–$600), $2M CGL, WSIB (roofing carries higher rates due to fall risk), and Working at Heights certification for the crew.
Working at Heights is a mandatory Ministry of Labour-approved training program for workers who use fall-protection on construction projects. It is legally required before a worker can be on a roof, and certification must be renewed every three years.
Commercial roofing warranties (and much of the higher-margin work) require installation by a manufacturer-certified contractor — GAF, Carlisle, Soprema, IKO, Firestone, Sika Sarnafil. Becoming a certified installer unlocks system warranties clients demand.
A sole proprietorship is cheaper and simpler to start, but you are personally liable for the business's debts and claims. Incorporating creates a separate legal entity that limits personal liability, can reduce tax once you are profitable, and reads as more credible to larger clients. Most contractors incorporate once they have employees, real revenue, or work on others' property.
Yes — construction is a mandatory WSIB sector in Ontario. Even independent operators and partners with no employees generally must register, and clients and general contractors will require a valid WSIB clearance certificate before you can work on their site.
You must register for and charge HST once your revenue exceeds $30,000 over four consecutive quarters. Many contractors register before that threshold so they can claim input tax credits on tools, materials, and vehicles from day one.
Ontario's Construction Act sets the rules: a 10% holdback on most contracts, prompt-payment timelines (you must be paid within set periods after a proper invoice), and an adjudication process for disputes. Understanding holdback, lien rights, and prompt payment is essential to protecting your cash flow.