Best roofing software for new roofing contractors (just starting out)

You just started your roofing business. Maybe you're solo for now, maybe you've got one or two people on payroll, and you're trying to figure out what software you actually need from day one.

Here's the honest answer: less than the software vendors will try to sell you.

If you've already read our solo contractors guide, this post overlaps but isn't the same. Solo is "established but small." This post is "brand new" — no entrenched workflow, no historical data to migrate, no team members to onboard. Different starting line.

What "new" actually means for software buying

A new contractor has constraints established shops don't:

• No revenue history. You don't know yet whether you'll close 3 deals a month or 30. Committing to annual contracts is a gamble.
• No workflow muscle memory. You're not migrating from a thing that worked — you're learning what works. Complex platforms with steep learning curves cost more in lost weeks than they save in features.
• No team to coordinate. "Multi-user CRM with role permissions" is solving a problem you don't have yet. You're the user.
• Limited capital. Spending $500/month on software before your first close is real money. Free or pay-as-you-go matters disproportionately.
• Need to look professional NOW. Your proposal has to look like you've been doing this for 10 years even though you started last month. Polish matters; depth doesn't yet.

With those weighted, here's what to start with.

The starter stack for a brand-new roofer ($0 to start, scales with you)

1. Roofr Starter — your free first CRM + proposal builder

Roofr's permanent free tier is the right place to start. You get:

• 3 included seats (room for your first hire without changing tools)
• A polished proposal builder that produces a sendable, professional quote on your first attempt
• Kanban pipeline for tracking leads from "called about a leak" → "signed contract"
• Customer-facing payments
• $19/report pay-as-you-go measurements (24-hour turnaround), so you only pay when a real lead converts to a measurement order

Why this matters for you specifically: you can run your business through Roofr from day one without a credit card on file. When you close your first 3 deals, you've paid maybe $57 in measurement reports. Compare that to committing to a $250/month CRM before your first sale.

When you outgrow the free tier (faster turnaround, SMS automations, more seats), the upgrade path is clear: Essentials at $209/mo annual.

2. GAF QuickMeasure — for measurements outside Roofr's network

You don't need a second measurement tool, but having one as a backup matters more than new contractors expect. Sometimes a Roofr report doesn't come back accurate on a complex roof. GAF QuickMeasure is $18/report, under 1 hour turnaround, no subscription.

Keep it in your pocket. Use it when:

• The property is in a coverage edge case
• You need a fast turnaround (a customer is comparing quotes today)
• You want a second opinion before bidding a large job

Total monthly cost of the starter stack: $0 base + ~$19–$37 per closed lead that needs measurement. You'll pay maybe $50–$200/month for the first 6 months.

When to start thinking about the upgrade path

Roofr Starter works indefinitely for shops sending fewer than ~10 quotes a month. The moment you cross that threshold consistently, you're at a decision point.

The two main paths:

Path A — Stay on Roofr, upgrade to Essentials ($209/mo annual)

Best fit if Roofr's workflow has become muscle memory and you want to keep one tool for everything. The Essentials tier unlocks 2-hour measurement turnaround (down from 24), better SMS automation, and 5 seats.

Path B — Switch to Artemis for design speed ($7.13/design)

Best fit if you've started competing on speed-to-quote. Artemis ships an AI-generated design in 5–15 seconds — meaningful when you're sitting at a homeowner's kitchen table and your competitor is "going back to the office to put a number together." Per-design pricing scales with your closing rate rather than your seat count.

Either path works. The question is whether your bottleneck is the proposal polish (stay with Roofr) or the close speed (move to Artemis).

See the head-to-head.

What to skip until you're bigger

These are good products for the right ICP. They're not the right ICP for you yet:

• JobNimbus — sales-gated, with real cost landing around $1,500/month for a small shop after add-ons. Built for established 5–50-person operations. Revisit when you have 5+ people on payroll.
• AccuLynx — $250/mo entry plus $500+ implementation, sized for mid-market insurance-restoration shops. Wait until you have an established insurance book.
• EagleView — gold-standard measurement at $18–$24/report, but better consumed via Roofr's bundled measurement until you specifically need ESX export for insurance work.
• iRoofing — $149/mo flat tablet-first setup. Skip if you don't have an iPad or aren't selling in-home.
• Hover — $25/job per-job for 3D capture and visualization. Add when you're consistently selling at the kitchen table and want a visual upgrade to the close.

The new-contractor mistakes worth avoiding

A few patterns we've seen on contractor forums from people who restarted their stack within their first year:

1. Don't sign an annual contract before your first 6 months of revenue. You don't know your volume yet. Pay-as-you-go or month-to-month is worth the slight premium.
2. Don't buy the platform your bigger competitor uses. What works for a 20-person shop is overkill (and over-priced) for you. Buy for your size.
3. Don't pay for measurement subscriptions before you're hitting the volume that justifies them. Per-report at $19 (Roofr) or $18 (QuickMeasure) is cheaper than any subscription until you're past ~15 reports/month.
4. Don't over-engineer the CRM before you have customers. Kanban with "lead → quote → close → install" is plenty. You don't need automated drip campaigns yet.
5. Don't forget about the contract/proposal moment. This is the moment that closes deals. Spend more time learning Roofr's proposal builder than learning the CRM pipeline. The proposal is the product, in your customer's eyes.

The one-year plan

Concretely, here's what most successful new roofers we've watched do over their first year:

• Months 1–3: Roofr Starter (free) + GAF QuickMeasure ($18 PAYG). Focus on closing the first 10 deals.
• Months 4–6: Still on Roofr Starter; budget for QuickMeasure reports as needed. Decide whether to upgrade to Essentials based on volume.
• Months 7–12: Either upgrade to Roofr Essentials ($209/mo) if you've outgrown the 24-hour turnaround, OR move to Artemis ($7.13/design) if speed-of-quote is your competitive advantage.
• Year 2+: Re-evaluate the full landscape. By now you know whether you're going to be retail-only, insurance-heavy, or mixed, and you can pick the right depth.

See our top 8 ranking for the full per-product breakdown.

Got questions, or a different path that worked for you?

We update this guide quarterly. If you're a new contractor and our framework doesn't match your reality, tell us — first-year experiences are the hardest signal to collect and most valuable to publish.