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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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