A roofing company can generate millions in revenue and still struggle with low profits, employee turnover, and an owner who can’t take a day off.
In this episode of the Roofing Success Podcast, Jim Ahlin sits down with Ryan Gregory, founder of Resilient Guides, to discuss what actually makes a roofing business valuable.
After growing and selling his own roofing company in Wyoming, Ryan now helps business owners build stronger teams, improve profitability, and create businesses that don’t depend on them for every decision.
Why Revenue Isn’t the Best Measure of Success
Roofing contractors often measure success by how much revenue their companies generate. Ryan admits he once focused on that number, too.
But bigger doesn’t always mean better.
A $20 million roofing company with strong profit margins and efficient operations can be more valuable than a $100 million company struggling to make money.
Ryan learned to focus on gross profit, identify his most profitable services, and turn down work that didn’t make financial sense.
The lesson? Stop chasing revenue for the sake of growth. Focus on building a profitable, sustainable business.
Build a Roofing Company That Runs Without You
One of Ryan’s biggest turning points was hiring a strong COO and implementing systems that allowed his team to make decisions independently.
Instead of managing every detail, Ryan could focus on the company’s vision and long-term growth.
That decision proved especially valuable after a serious skiing accident left him unable to work. While he focused on recovery, his roofing company continued operating successfully.
The business no longer depended on him.
For roofing contractors, this is the difference between owning a business and owning a job. If everything stops when you step away, there’s still work to do.
How Systems Increased His Company’s Value
Ryan eventually sold his roofing company to a strategic buyer. He shared that the business received a valuation approximately five times the typical industry EBITDA valuation benchmark he referenced.
Why? The company had strong leadership, established processes, and the ability to operate without its owner.
The buyer wasn’t just purchasing revenue or equipment. They were buying a functioning organization.
Even if you’re not planning to sell, building these systems gives you more freedom today and creates a more valuable asset for the future.
Hire the Right People and Build a Strong Culture
Looking back, Ryan wishes he had slowed down when hiring for important positions.
His advice is to hire people who align with your company’s core values, not just candidates with impressive resumes.
He also emphasizes regular employee conversations, clear accountability, and opportunities for professional growth.
For Ryan, company culture went beyond the workplace. His roofing business regularly gave back to the community, including donating roofs to veterans, teachers, and first responders.
That mission gave employees something bigger to work toward.
When people believe in the company’s purpose, they’re more likely to take ownership of their work and contribute to its success.
Learn to Delegate and Develop Leaders
Many roofing owners struggle to delegate because they’re used to being involved in everything.
Ryan believes that mindset limits growth.
Instead of trying to handle every responsibility, owners should identify where they bring the most value and develop employees to manage the rest.
But delegation requires more than assigning tasks. It takes clear expectations, coaching, and consistent feedback.
Ryan recommends making delegation a regular part of your schedule.
The goal isn’t to become less involved overnight. It’s to build a team capable of making decisions and solving problems without constantly needing your approval.
Get Outside Help to Grow Your Roofing Business
Ryan credits much of his success to learning from other business owners, mentors, and coaches.
He recommends three things for roofing contractors looking to grow:
- Join a peer group to learn from contractors facing similar challenges.
- Use a business operating framework to create accountability and improve processes.
- Invest in coaching to develop your leadership skills.
Ryan’s company invested heavily in outside guidance because it helped his team improve operations, profitability, and long-term planning.
Build a Business Worth Owning
The biggest takeaway from Jim and Ryan’s conversation is simple: A successful roofing company should give you more freedom, not consume your entire life.
Revenue matters, but profitability, leadership, culture, and systems are what create lasting value.
Whether you plan to sell your company or run it for another 20 years, focus on building something that can succeed without you.
Learn more about Ryan Gregory and his work at Resilient Guides.
