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How Insurance Supplementing Has Changed and What Roofing Contractors Must Do to Stay Profitable

📅 August 7, 2026 ⏱️ 31:08 🎤 Phil Milstein, Randy

Chapters

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  • 0:00
    Evolving Supplementing Landscape
    The hosts introduce Phil Milstein to discuss the ever-changing challenges and strategies in insurance supplementing for roofing contractors.
  • 0:42
    Phil's Entrepreneurial Journey
    Phil shares his background as a fourth-generation entrepreneur, from selling candies in middle school to his current role leading Ideal Claim Solutions.
  • 16:43
    Key Supplementing Strategies
    Phil outlines essential strategies for contractors, including understanding insurance paperwork and identifying recoverable depreciation and building code coverage.
  • 22:19
    Recent Changes in Supplementing
    The discussion covers how insurance companies' tactics, like contractor networks and changing building code policies, have significantly impacted the supplementing process.
  • 33:53
    Training Sales Reps for Claims
    Phil advises contractors on training sales representatives to educate homeowners about the insurance process, highlighting the value of specialized teams for supplements.
  • 42:12
    Must-Do for Supplement Success
    Phil stresses the importance of detailed photo documentation and presenting clear, side-by-side comparisons of estimates for successful supplementing.
  • 48:13
    The Value of a Business Coach
    Phil concludes by emphasizing the critical role of having a business coach or mentor for external perspective and guidance in entrepreneurship.

Speakers

P
Phil Milstein
Owner, Ideal Claim Solutions
R
Randy
Host

Key Takeaways

✦

Understand insurance paperwork, including the statement of loss, to identify recoverable depreciation and building code coverage before structuring your supplement.

✦

Be aware of how insurance companies are influencing the market through their contractor networks and understand their implications for your pricing and client relationships.

✦

Thoroughly document all damage with comprehensive photos, mimicking and exceeding what adjusters capture, including often-missed elements like pre-existing starter course on rakes.

✦

When submitting supplements, provide a clear, side-by-side comparison of your estimate with the adjuster's original scope to streamline the review process for the insurance company.

✦

Educate homeowners about the insurance process, explaining paperwork and potential out-of-pocket costs, to build trust and position your company as a reliable guide.

✦

Consider specializing roles within your company for insurance claims; dedicated supplement specialists can be more efficient and up-to-date on trends than sales reps handling supplements themselves.

✦

Leverage building code coverage, especially for items not pre-existing (like decking), as these may be paid at 100% replacement cost value, significantly reducing homeowner out-of-pocket expenses.

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