How to Recover Thousands on Insurance Jobs Without Endless Paperwork

You finished the inspection. Hail damage everywhere. Clear-cut total replacement. Then the insurance estimate comes back, and it's $4,000 less than what the job actually costs.

Sound familiar? You're not alone, and you're not imagining things.

The Real Cost of Accepting First Offers

Insurance adjusters aren't trying to rip you off. They're working from Xactimate estimates that may not reflect your actual costs. The problem is, those estimates can come in lower than what the job really requires.

Many roofing contractors report losing thousands per insurance job by accepting first-offer settlements without pushing back. The exact amount varies by market, carrier, roof size, and scope, but run the math on your last year of insurance work. If you did 20 storm jobs and left even $2,000-$4,000 per job on the table, that's $40,000-$80,000 in missed revenue.

That's not a rounding error. That's a new truck. That's another crew. That's your profit margin. And combined with building a proper winter cash reserve, proper supplementing is what separates roofing businesses that thrive from those that struggle.

Why Insurance Estimates Come Up Short

Xactimate is one of the most widely used estimating platforms for insurance claims. Adjusters plug in the measurements, select the materials, and the software spits out a number. Simple, right?

Here's what often gets missed:

Pricing can lag behind local reality. According to the Bureau of Labor Statistics Producer Price Index for asphalt shingles, roofing material costs saw significant increases between 2020 and 2022. Xactimate regional pricing doesn't always keep pace with actual supplier costs in your specific area.

Legitimate line items get omitted. Drip edge, pipe boots, step flashing, permit fees, code-required upgrades. These items exist in Xactimate but often aren't included unless the estimator specifically adds them or you document and request them.

Labor calculations assume ideal conditions. Steep roofs, multiple stories, limited access, removing satellite dishes. None of that shows up automatically.

Overhead and profit get challenged. Some carriers may challenge the inclusion of overhead and profit (O&P), which is often calculated as 10% overhead and 10% profit. Be prepared to justify these costs if you include them.

These pricing and scope gaps are well-known in the industry. It's just that most contractors don't know how to fight back effectively.

The Manual Fix: A Supplement System That Works

You don't need special software to start recovering this money. You need a process.

Step 1: Document Everything Before You Touch the Roof

Your supplement is only as strong as your evidence. Before any work begins:

• Take plenty of photos, often 30-80 depending on complexity. Wide shots, close-ups, measurements in frame.
• Photograph every damaged component. Not just shingles. Drip edge, vents, flashing, gutters.
• Document roof access issues. Steep pitch, height, obstacles, distance from driveway.
• Note code requirements. Ice and water shield required under your state/local building code as adopted? Synthetic underlayment required? Get it in writing from your building department, citing the exact adopted code section.

Use timestamps on every photo. Adjusters can't argue with dated evidence.

Step 2: Build Your Line-Item Checklist

Create a standard checklist of items that insurance estimates commonly omit. Check it against every estimate you receive:

Materials frequently excluded:

• Drip edge (all edges, not just rake)
• Pipe boot replacement
• Step flashing and counter flashing
• Ridge vent or box vents
• Starter strip (both rake and eave)
• Ice and water shield (check your state/local building code requirements)
• Synthetic underlayment upgrades

Labor items often missed:

• Steep charge (often starts around 7/12 pitch, but varies by estimating system and carrier)
• High charge (2+ stories)
• Limited access
• Detach and reset charges (satellite dishes, solar panels, HVAC equipment)
• Debris removal beyond dumpster
• Permit fees

Overhead and profit:

• O&P is commonly cited at 10% overhead and 10% profit, but this varies by carrier, jurisdiction, and whether a general contractor is reasonably required for the scope of work

Check your state DOI guidance, case law, and carrier guidelines on O&P, as rules and interpretations vary.

Step 3: Write a Professional Supplement Letter

Your supplement letter is your case for more money. Keep it factual and professional. Here's a template you can adapt:

SUPPLEMENT REQUEST

Claim Number: [Number] Insured: [Homeowner Name] Property Address: [Address] Date of Loss: [Date]

Dear Claims Adjuster,

After completing our inspection of the above property, we have identified the following items that were not included in the original estimate but are necessary to complete repairs in accordance with local building codes and manufacturer specifications:

1. Drip Edge Replacement (All Edges) - [Linear feet] LF Original estimate included eave drip edge only. Rake edges also require replacement per manufacturer warranty requirements.
2. Ice and Water Shield - [Square feet] SF Required by [Your State/County] building code [cite specific code section] for [specified distance] from eave edge. Not included in original estimate.
3. Steep Roof Charge - Roof pitch is [X]/12 Per OSHA regulations (29 CFR 1926 Subpart M), fall protection and safe access measures are required on steep roofs, which increases labor costs and reduces production rates. Many estimating systems apply steep/high adders for these conditions.

Please see attached photos documenting each item. We are available for a re-inspection at your convenience.

Respectfully, [Your Name] [Company] [License Number]

Step 4: Follow Up Relentlessly

Submit your supplement as soon as practicable after receiving the original estimate. Confirm any carrier deadlines that may apply. Then follow up:

• Day 3: Email confirmation that supplement was received
• Day 7: Phone call to check status
• Day 14: Second follow-up call
• Day 21: Escalation request if no response

Keep a log of every contact. Adjusters handle hundreds of claims. The contractors who follow up get paid. The ones who don't get forgotten. The same principle applies to any business communication. Staying on top of customer calls and inquiries separates businesses that grow from those that stagnate.

Step 5: Know When to Escalate

If a line item gets denied, ask for the specific reason in writing. Common pushback and responses:

"That's not Xactimate pricing." Response: Provide supplier invoices showing actual material costs in your area.

"O&P is only for general contractors." Response: Check your state DOI guidance, case law, and carrier guidelines. Some states and courts have supported O&P for specialty contractors under certain conditions.

"We don't pay for code upgrades." Response: Some policies include ordinance or law coverage, though it's often optional or limited by endorsement. Review the declarations, endorsements, and policy language to verify what's covered.

If you're still stuck, suggest a re-inspection with you on-site. Being there in person changes the dynamic.

The Numbers on a Real Job

Here's what proper supplementing looked like on one specific roofing job:

Original estimate: $12,400

Items missing from original:

• Drip edge (all edges): $380
• Pipe boots (3): $210
• Step flashing: $440
• Ice and water shield: $680
• Steep pitch charge: $1,860
• High roof charge: $620
• Permit fee: $350
• O&P (was reduced): $1,640

Supplemented total: $18,580

Additional claim value approved: $6,180

That's one job. The supplement took about 25 minutes to prepare. Not every job will yield that much, but the time invested in proper documentation consistently pays off.

A Better Way

Here's the reality: the supplement process works, but it's tedious. You're cross-referencing Xactimate line items, hunting for photos, writing letters, tracking follow-ups, and doing it over and over for every insurance job.

This is exactly the kind of repetitive, documentation-heavy work where automation makes sense. The same one-touch admin methods that eliminate evening paperwork for contractors apply perfectly to insurance supplement tracking.

AI tools are emerging that can help organize and tag your inspection photos, suggest likely Xactimate line items, and draft supplement letters for your review. They can track which supplements are pending and which need follow-up. However, human review and adjustment are still typically required, and integration depends on your storage, CRM, and Xactimate workflow.

The same documentation workflows that speed up regular proposals work even better for insurance supplements, where the stakes are higher and the details matter more.

You still need to know what to ask for. You still need to understand the process. But the mechanical parts, the photo sorting, the letter drafting, the follow-up tracking, don't have to eat your evenings.

The Bottom Line

Insurance supplements aren't about being aggressive or adversarial. They're about getting paid for the actual work required to do the job right. Adjusters expect supplements. Carriers budget for them. The contractors who understand the process get paid fairly. The ones who don't subsidize everyone else's claims.

Start with the checklist. Document everything. Follow up consistently. That alone can recover significant revenue this year.

If you want help systemizing this, whether it's supplement assistance, documentation workflows, or follow-up tracking, the right systems can make a significant difference. There's too much money getting left on roofs.

This blog post is for informational purposes only and should not be considered legal advice. Consult with a qualified legal professional to ensure compliance with all applicable state and local regulations.