The Roofing Operating System Podcast: America’s Top-Rated Podcast for Roofing Software & Scalable Growth

#6 - How this Roofer Scaled to $20M with JobNimbus

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How a Struggling Roofer Built a $20M Business Using CRM, Data, and Discipline


Ft. Randy Brothers + Better Boss + JobNimbus

In this powerhouse episode of The Roofing Operating System Podcast, host Nick Peret (Founder of Better Boss) sits down with one of the most respected leaders in roofing—Randy Brothers, founder of The Roofing Academy and Elite Roofing.

Randy went from near collapse to building a $20M+ company, and in this conversation, he lays out exactly how he did it—from implementing systems and automations to mastering job costing, team structure, and sales psychology.

This isn’t theory. This is the real playbook.

Whether you’re doing $500K or $5M+, this is how you scale—intentionally, profitably, and without losing your mind.

🔧 What We Cover in This Episode:

  • The exact CRM and proposal tools (JobNimbus, SumoQuote) Randy used to grow

  • Why job costing is the foundation of every great roofing company

  • How to lead your team through chaos, burnout, and big growth

  • Why “winging it” with software is what’s actually holding you back

  • The number one mistake contractors make when trying to scale

  • How to fix your finances, sales systems, and profit tracking—fast

    ⚡ Timestamps (Callout Format):

    00:00 Welcome – How Better Boss Helps Roofers Scale with Systems

    00:12 Meet Randy Brothers – From General Contractor to Roofing Legend
    04:49 The Collapse: Recession, Personal Struggles & Rebuilding
    11:00 Hypergrowth: The Systems + Team That Made $20M Possible
    14:00 Why JobNimbus + SumoQuote Changed Everything
    24:21 Job Costing, Cash Flow, and Profit-First Thinking
    29:44 Data, Dashboards & Running a Business Like a CEO
    33:51 The Truth About Roofing Business Growth (It’s Not Hustle)
    45:17 Final Words for Roofers: Focus, Frameworks, and Freedom

    💥 Who Should Watch This:

    • Roofing business owners who want to stop being “in the weeds”

    • Contractors doing $1M–$10M who need better ops, finance, and tech

    • Sales leaders trying to scale without dropping the ball

    • Anyone tired of duct-taping together tools and hoping they work

      🛠 Powered by:

      Better Boss — The CRM + Automation Platform Built to Scale the Smartest Roofing Companies in America.

      🎯 Train with Randy:

      Ready to turn your business into a machine? Learn from the system that built a $20M brand:

      👉 https://www.theroofingacademy.com

      🏷️

      #RoofingBusiness #RoofingSystems #JobNimbus #SumoQuote #BetterBoss #RoofingCRM #RandyBrothers #TheRoofingAcademy #RoofingSales #CRMRoofing #RoofEstimating #RoofingAutomation #RoofingLeadership #RoofingScaling #ConstructionTechTalk #NickPeret

       

      💥 That’s a wrap on another episode of The Roofing Operating System™—America’s top-rated podcast for roofing software and scalable growth.

      If today’s insights sparked just one idea to scale smarter or grow faster, imagine what a full strategy could do for your business.

      👉 Head to mybetterboss.ai to access free tools, book a discovery call, or explore systems trusted by top roofing companies nationwide.

      Don’t forget to follow the show, leave a 5-star review, and share it with another roofer ready to level up.

      Until next time—build better, lead stronger, and scale like a boss.

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      The Roofing Operating System Podcast: America’s Top-Rated Podcast for Roofing Software & Scalable GrowthBy Nick Peret