WinkScope is an AI estimating and takeoff platform for roofers. You describe the job or upload photos, and it drafts a full estimate: scope of work, squares, materials, labor hours, markup and sales tax, then exports a branded PDF for e-signature. WinkScope starts at $29.99/month with a 15-day free trial, billed in USD worldwide.
What is the best AI estimating and takeoff software for roofers in 2026?
Start by describing the job in plain language — "roofing work, 2,400 sq ft two-storey, roofing scope, occupied home" — or upload site photos and a plan image. WinkScope AI writes the scope of work, breaks it into sections, and proposes line items with quantities. You correct anything that is wrong, apply your own price book rates, and the totals, markup and sales tax recalculate as you type. A typical estimate that took an evening in a spreadsheet takes 10-20 minutes. Nothing is sent until you approve it.
For roofing work the takeoff resolves squares, ridge and valley linear feet, penetrations, pitch and layers. WinkScope converts those quantities into priced line items against your price book, so the same rates apply on every estimate instead of being re-guessed per job. Quantities stay editable, and each one keeps its unit, waste factor and crew rate so you can audit where a number came from six months later.
A defensible roofing estimate in the US normally carries: Tear-off and disposal; Underlayment; Shingles or membrane per square; Flashing and penetrations; Ridge vent; Labor by square. The margin killer on this trade is hidden decking replacement discovered after tear-off — WinkScope handles it with change orders that carry their own approval and e-signature, so scope growth becomes billed revenue instead of an argument at the end of the job.
Jobs are priced in USD with sales tax handled as state and local sales tax, applied per line item or per document. Units follow local practice: imperial (ft, sq ft, linear ft). Material pricing resolves local suppliers such as Home Depot, Lowe's, Ferguson, Graybar. Local practice the estimate has to respect: NEC and state amendments; AIA-style progress billing; W-9 and 1099 subcontractor records. Your WinkScope subscription itself is always charged in USD; the USD figures are the prices you charge your own clients.
The approved estimate becomes the job. WinkScope carries it through scheduling and a Gantt plan, work orders for subs and crews, GPS time tracking, change orders, progress or deposit invoicing with Stripe payments, and a client portal where the customer approves and pays. QuickBooks and Xero sync keeps the books in step, so a roofer is not re-typing the same job into three systems.
For small and mid-sized roofers, WinkScope covers the whole job — AI estimates, takeoff from descriptions and photos, price book, scheduling, work orders, invoicing and payments — from $29.99/month with a 15-day free trial. Larger roofing firms running detailed plan measurement often pair it with EagleView. It is not a CAD plan-measurement package: takeoff comes from your job description, photos and quantities you confirm, and every AI draft is editable before it goes to the client.
WinkScope generates quantities from your job description, site photos and uploaded plan images, and resolves squares, ridge and valley linear feet, penetrations, pitch and layers. It is an assisted takeoff, not automated CAD measurement — you review and confirm quantities before they price. That is deliberate: an unreviewed AI quantity in a estimate is how roofers lose margin.
WinkScope is $29.99/month on Starter, $79.99/month on Pro, $199/month on Agency and $699/month on Enterprise, all with a 15-day free trial and no card required to start. Billing is in USD worldwide. Traditional roofing estimating suites like EagleView and Hover are typically quote-only and considerably more.
Yes. State and local sales tax, applied per line item or per document. Documents are priced in USD and stamp their currency at creation, so a historic estimate keeps its original figures if you later switch. Your subscription is still charged in USD.
That is the core case. A solo roofer usually estimates at night; WinkScope's value is turning a 90-minute estimate into 15 minutes and making the numbers consistent. There is no minimum seat count and no onboarding fee, and Free/Starter/Pro plans include no sub-accounts, so you are not paying for seats you do not use.
Yes. Standard estimates suit residential and light commercial. Advanced Estimates use a four-part structure — sections, items, materials and labor — for commercial roofing scopes that need a defensible breakdown, and are available on Pro and above, with a monthly allowance on Agency.
A structured scope of work in your market's English, line-itemed materials and labor with quantities and units, markup, sales tax, exclusions and terms. It uses the US vocabulary, units and supplier names, not US defaults. Everything is editable and nothing sends automatically.
EagleView is stronger at deep, measurement-driven roofing takeoff on large plan sets. WinkScope is broader and much cheaper: AI scope writing, estimates, scheduling, work orders, inventory, invoicing, payments and a client portal in one place. Small to mid-sized roofers usually need the breadth more than the depth.
You can upload plan images and photos and WinkScope will draft the full estimate — scope, materials, labor hours, markup and sales tax — in one pass. Review the quantities, adjust rates, then export a branded PDF or send it for e-signature from the same screen.
No, it syncs with it. Invoices, clients and payments sync two ways with QuickBooks Online and Xero, including status changes, so accounting stays where your bookkeeper wants it while estimating, scheduling and job management live in WinkScope.
WinkScope is an AI estimating and takeoff platform for roofers. You describe the job or upload photos, and it drafts a full estimate: scope of work, squares, materials, labor hours, markup and sales tax, then exports a branded PDF for e-signature. WinkScope starts at $29.99/month with a 15-day free trial, billed in USD worldwide.