Most roofing owners scale by adding payroll. Chris Kane went the other direction and runs eight figures with a team you could fit in a truck.

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Chris Kane is the owner of 303 Roofer in Denver, Colorado, where he has spent 17 years building a roofing company that now runs just over $10 million a year. He came to roofing sideways, moving from TV and radio into consumer-advocacy work and a nonprofit that stepped in to finish jobs failed contractors had abandoned, which eventually pushed him to get licensed and do the work himself. Today he runs a deliberately lean operation with project managers, salespeople, and crews on 1099 contracts, and he's just started hiring door to door reps for the first time in the company's history.

In this episode Chris breaks down the subcontractor model honestly, including what it costs him. He explains why the company subcontracted early, moved to employees during a growth phase, then went back to subcontractors after COVID when the office closed and fixed payroll started looking like a liability instead of an asset. He's candid that the model trades sale valuation for stress and flexibility, and that around $15 million he expects to reevaluate it entirely.

What we get into:

• Why he reversed course on employees after COVID and closed the office for good
• The revenue math that makes one commercial reroof worth dozens of residential jobs
• Where residential leads actually come from versus commercial, and why they're nothing alike
• Why offering cash pricing instead of leading with insurance produces an 80% close rate on estimates
• The succession plan built around teaching a subcontractor to run a full-service company
• The threshold where a lean model stops working and structure becomes non-negotiable
• His one piece of legacy advice, and why it has nothing to do with roofing

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https://ownersos.com/?utm_source=youtube&utm_medium=description&utm_campaign=ownersos_roofing&utm_content=running_a_10m_roofing_company_with_almost_no_employees

#roofing #roofingceo #contractorlife #roofingbusiness #subcontractors

Jake Denning spent eight months moving All Ears Roofing from ninety percent insurance to ninety percent retail, trading the storm-chasing rollercoaster for predictable revenue.

Grab the free Business Playbook: https://ownersos.com/business-playbook?utm_source=youtube&utm_medium=description&utm_campaign=ownersos&utm_content=how-this-roofer-switched-from-insurance-to-retail

On the Roofing CEO Podcast, host Mike Abramowitz talks with Jake Denning, owner of All Ears Roofing (formerly Manchak Roofing) in Webster, Texas. Jake explains why he deliberately shifted from an insurance-driven model to a retail one to cut volatility, and how that forced him to rebuild the whole machine: separating canvassing from in-home sales, generating leads so reps run one to three appointments a day, and treating recruiting and a three-week training program as the real engine of growth. He shares how he and his partner split the business and why a five-star experience for both customers and employees is the priority on the road to twenty to thirty million.

Jake Denning is the owner of All Ears Roofing (rebranded from Manchak Roofing in 2025) in Webster, Texas, a retail-focused roofing company in the $5 to $10 million range. He came up through insurance and storm restoration before building a retail operation.

Questions this episode answers:

• How do you switch a roofing company from insurance to retail?
• Why go retail instead of insurance roofing?
• How do you recruit and train retail roofing sales reps?
• How do you build predictable revenue in roofing?
• How do you structure a retail roofing sales team?

What you'll learn in this episode:

• Why Jake moved from ninety percent insurance to ninety percent retail, and what it did for stability
• How the retail model forced a full redesign of hiring and sales roles
• Separating canvassing from in-home sales, and feeding reps one to three appointments a day
• Why recruiting and a three-week training program are the real scaling engine
• How he and his partner split marketing and sales versus training and production on the way to $20 to $30 million

This show is brought to you in partnership with Forge and D2D Experts. A predictable, sellable roofing company runs on systems, not on storms. Owner's OS is the operating system built for it: https://ownersos.com/?utm_source=youtube&utm_medium=description&utm_campaign=ownersos&utm_content=how-this-roofer-switched-from-insurance-to-retail

Connect with Jake: allearsroofing.com · Instagram @allearsroofing

How do you recruit young people into roofing and turn them into closers?

Andrew Matson runs Home Court Roofing like an entrepreneur factory, and one of his 20-year-old reps went from UPS night shifts to buying a Corvette.

Grab the free D2D Blueprint: https://ownersos.com/the-d2d-blueprint?utm_source=youtube&utm_medium=description&utm_campaign=ownersos&utm_content=how-to-recruit-and-develop-roofing-sales-reps-playbook

On this episode of the Roofing CEO Podcast, host Mike Abramowitz talks with Andrew Matson of Home Court Roofing in Louisville. Andrew treats his company as a place to develop reps and leaders, not just to sell roofs.

He walks through the 90-day curriculum he runs on new hires, the mindset shift from employee to value-seller, and his mission to make Home Court the premier place in Louisville for young people to learn roofing, sales, and entrepreneurship, including rebuilding university pipelines to bring in students every summer.

Andrew Matson has owned Home Court Roofing in Louisville, Kentucky for three years, with a leadership focus on developing young reps into closers and future leaders.

What you'll learn in this episode:

• The 90-day development curriculum Andrew runs on new hires
• How a 20-year-old went from UPS nights to $10k-plus months
• Building a roofing company as an entrepreneur factory
• Rebuilding university pipelines to recruit students every summer
• Why developing people beats chasing tactics in a changing insurance market

This show is brought to you in partnership with Forge and D2D Experts.

If you're a roofing CEO trying to get out of the day-to-day, Owner's OS is the operating system built for it: the org chart, role clarity, KPIs, and one-on-one system that let the business run without you.

Get the Owner's OS operating system: OwnersosOwnersOS helps home-service companies scale