The first question every homeowner asks is simple: “How much is this going to cost?”

In this episode, we talk about why roofing sales are changing fast — and why contractors who hide pricing or avoid the conversation are losing trust before they ever step foot on the property.

I’m joined by Mike Goldenstein from Roof Quote Pro to discuss how transparent pricing tools are reshaping the buying experience, improving lead quality, and helping contractors close more jobs with less friction.

Roofing sales are evolving, and homeowners expect faster answers, clearer pricing, and more transparency than ever before.

In this episode, Dave Sullivan sits down with Mike Goldenstein of Roof Quote Pro to break down how instant pricing tools are changing the way roofing contractors attract, qualify, and convert leads. Instead of forcing homeowners to wait days for an estimate, Roof Quote Pro allows contractors to provide real pricing ranges upfront — building trust before the first phone call.

Dave and Mike discuss why pricing transparency doesn’t hurt sales — it improves them. Contractors who embrace clear pricing often attract better leads, reduce tire-kickers, and shorten the sales cycle. The conversation also covers how technology fits into a larger system, supporting better marketing, stronger branding, and more efficient operations.

This episode is a must-listen for contractors who want to modernize their sales process, improve customer experience, and scale without burning out their sales team.

• Homeowners want pricing clarity early in the buying process
• Transparent pricing builds trust and improves lead quality
• Technology can shorten the sales cycle and reduce wasted appointments
• Clear systems make sales easier and more consistent
• Modern tools support growth without adding complexity

00:00 – Introduction to The Roofer Show

02:51 – Why Homeowners Ask About Price First

10:45 – The Problem With Hiding Pricing

16:18 – How Roof Quote Pro Works

21:55 – Transparency, Trust, and Conversion

28:25 – Technology’s Role in Modern Roofing Sales

35:56 – The Future of Roofing Sales

https://theroofercoach.com

https://roofquotepro.com

https://smasupport.us

Roof Quote Pro

SMA Support

👉 Download free tools and resources at

theroofercoach.com/resources

Most roofing businesses don’t fail because of a lack of work — they fail because of chaos.

In this episode, I sit down with John DeLaurier to talk about what it really takes to move from reacting all day to running a business with control, clarity, and confidence. We break down the systems every growing roofing company needs to handle more work without more stress.

Growth is exciting — until it isn’t.

Many roofing contractors hit a point where sales increase, but everything else starts to break. Jobs slip through the cracks, customers get frustrated, cash flow tightens, and the owner becomes the bottleneck. That’s not a growth problem — it’s a systems problem.

In this episode, Dave Sullivan talks with John DeLaurier about how contractors can move from daily chaos to operational control by installing simple, proven systems across sales, production, and administration. John shares real-world insights from working with contractors who scaled successfully — and those who didn’t — highlighting the key differences between the two.

They discuss why systems don’t slow you down, how clear processes improve accountability, and why documented workflows are essential if you want a business that can grow without relying on you for every decision.

If your business feels busy but fragile, this episode will help you understand what to fix — and where to start.

• Growth without systems creates stress, not freedom
• Clear processes improve accountability and consistency
• Systems reduce errors and improve customer experience
• Owners must stop being the bottleneck to scale
• Control comes from clarity, not working harder

00:00 – Introduction to The Roofer Show

03:45 – Why Growth Creates Chaos

09:30 – The Difference Between Busy and Scalable

15:20 – Systems That Create Control

23:10 – Accountability Through Process

31:45 – Getting the Owner Out of the Bottleneck

39:20 – Building a Business That Runs Without You

https://theroofercoach.com

https://theroofercoach.com/resources

The Roofer Coach

👉 Download free tools and resources at

theroofercoach.com/resources

If you’re not offering financing in your roofing business, you’re losing jobs — even when homeowners like you.

In this episode, I’m joined by Chris Scoville from Improvify to break down why financing is no longer optional for roofing contractors and how the best companies are using it as a sales system, not a last-minute add-on.

We talk about when to introduce financing, how to train your sales team to use it confidently, and why presenting payment options early creates trust instead of pressure. Financing isn’t about discounting your price — it’s about removing friction and helping homeowners say “yes” sooner.

This conversation is about building a smoother sales process, increasing close rates, and making it easier for good customers to move forward without stressing over the full upfront cost.

Most roofing contractors think financing is just a tool for customers who “can’t afford it.”

That mindset is costing them deals.

In this episode, Dave Sullivan sits down with Chris Scoville of Improvify to explain how financing should be built directly into your sales system — not treated as a backup option when a homeowner hesitates.

They discuss why homeowners expect financing today, how offering it early actually increases trust, and why waiting until the end of the sales conversation often kills momentum. Chris shares practical insights on training sales reps to confidently present financing, positioning it as a service rather than a pitch, and avoiding common mistakes that create confusion or resistance.

You’ll also hear how top roofing companies use financing to increase average job size, improve close rates, and create a better overall customer experience — without racing to the bottom on price.

This episode is essential listening if you want to close more jobs, reduce price objections, and build a more professional, modern roofing business.

• Financing should be introduced early — not as a last-minute save

• Homeowners expect payment options and trust contractors who offer them

• Financing increases close rates without lowering your price

• Sales reps need training and systems to present financing confidently

• Clear payment options reduce friction and shorten decision time

• Financing is a sales tool, not a desperation move

00:00 – Introduction to Roofing Financing

01:49 – Why Financing Is No Longer Optional

08:02 – How Top Roofers Present Financing Early

18:31 – Training Sales Teams to Use Financing

22:52 – Removing Price Objections Without Discounting

27:19 – Building Financing Into Your Sales System

https://theroofercoach.com

https://theroofercoach.com/resources

https://improvify.com

https://useproline.com

Improvify

Proline

👉 Download free tools and resources for roofing contractors at

theroofercoach.com/resources

Most roofing contractors say the same thing:

But the real problem usually isn’t the labor market — it’s how you’re hiring.

In this episode, I’m joined by Paul Sandeman from Contractor Staffing Source to break down what it actually takes to attract, hire, and retain A-players in a roofing business. We talk about why most contractors hire out of desperation, why that cycle never works, and how to build a hiring system that brings in high-quality people consistently.

This isn’t about posting another job ad and hoping for the best. It’s about building a business that talented people want to work for — with clear roles, accountability, and leadership that doesn’t depend on the owner doing everything.

If you want a roofing company that runs without constant chaos, hiring right is not optional.

Hiring mistakes are one of the fastest ways to kill profit, culture, and momentum in a roofing business.

In this episode, Dave Sullivan sits down with Paul Sandeman of Contractor Staffing Source to explain why most roofing contractors struggle to find good people — and what to do instead. The conversation focuses on building a repeatable hiring system that attracts A-players rather than settling for whoever is available.

We cover why reactive hiring leads to turnover, burnout, and bad culture, and how proactive recruiting changes everything. Paul explains how top contractors think differently about hiring, including faster response times to applicants, better screening, and clearer expectations from day one.

This episode is especially important if you want a business that doesn’t rely on you personally — one that can grow, scale, or eventually be sold.

• Good people aren’t hard to find — good hiring systems are
• Hiring out of desperation almost always leads to costly mistakes
• A-players want clarity, structure, and leadership — not chaos
• You must always be recruiting, even when you’re “fully staffed”
• Strong culture and accountability attract better talent
• A business that depends on the owner can’t scale or be sold

00:00 – Why Roofing Contractors Struggle to Hire

03:40 – The Real Cost of Bad Hires

08:15 – Why “Nobody Wants to Work” Is the Wrong Mindset

13:20 – What A-Players Actually Look For

18:45 – Building a Repeatable Hiring System

24:10 – Speed Matters: Responding to Applicants

30:05 – Screening, Assessments, and Fit

36:30 – Culture, Accountability, and Retention

43:15 – Hiring for a Business That Runs Without You

https://theroofercoach.com

https://theroofercoach.com/resources

https://contractorstaffingsource.com

https://smasupport.us

https://useproline.com

Contractor Staffing Source

SMA Support

Proline

👉 Looking to build a roofing business that doesn’t rely on you?

Download the Roofing Business Success Audit at

theroofercoach.com/resources

Most roofing contractors work hard for years assuming they’ll eventually sell their business or pass it on.

The reality?

Most businesses don’t sell — they simply shut down.

In this episode, I sit down with construction attorney Scott Calhoun to break down the four biggest business killers that quietly destroy roofing companies: divorce, disability, dissolution, and death.

These aren’t dramatic what-ifs. They’re predictable risks that can wipe out everything you’ve built if you don’t plan ahead.

We talk through real-world examples of contractors who didn’t have the right structure, agreements, or protections in place — and what you can do now to protect your company, your family, and your future. This episode is about building a business that survives real life, not just good years.

If your roofing business depends entirely on you, it’s more fragile than you think.

In this episode of The Roofer Show, Dave Sullivan is joined by construction attorney Scott Calhoun to discuss the Four Business Killers that end most contractor-owned companies long before retirement: divorce, disability, dissolution, and death.

They break down why most roofing businesses never sell and why failing to plan for these risks leads to forced closures, legal battles, and financial loss. Scott explains how proper entity structure, partnership agreements, buy-sell planning, and insurance can protect both the business and the people behind it.

This conversation isn’t about fear — it’s about foresight. With the right planning and systems in place, contractors can build businesses that withstand unexpected life events and continue operating without chaos. If you care about long-term stability, profitability, and protecting what you’ve built, this is a must-listen.

• Most roofing businesses don’t fail from lack of work — they fail from lack of planning
• Divorce, disability, dissolution, and death are predictable risks, not rare events
• Proper entity structure protects both the business and personal assets
• Partnership and buy-sell agreements prevent chaos during major life events
• Disability can be more financially damaging than death if not planned for
• A business that can’t survive without you isn’t a sellable or stable business

00:04 – Understanding the Four Business Killers

09:41 – How the 4 Ds Impact Roofing Companies

25:12 – Real-World Contractor Scenarios

36:10 – Succession Planning and Business Continuity

42:42 – Disability Insurance and Risk Protection

https://theroofercoach.com

https://theroofercoach.com/resources

SMA Support

Proline

👉 Download the free Roofing Business Success Audit at

theroofercoach.com/resources

Most roofing businesses don’t fail because of a lack of work — they fail because the fundamentals aren’t in place.

In this episode, I break down the core business essentials every roofing contractor needs to focus on to build a more profitable, stable, and sustainable company in 2025 and beyond. This isn’t about chasing the latest tactic or tool. It’s about strengthening the foundation that supports real growth.

We cover the critical areas that consistently separate profitable roofing companies from those stuck in constant firefighting: financial clarity, systems, leadership, and disciplined execution. If you want more control, better margins, and a business that doesn’t rely entirely on you, this episode lays out where to focus first.

Every year, roofing contractors set new goals — and many of them still end up frustrated, overworked, and wondering why the numbers don’t improve.

In this episode, Dave Sullivan outlines the essential business fundamentals roofing contractors must master to increase profitability and regain control of their companies. These principles apply whether you’re running a small operation or scaling a multi-million-dollar business.

Dave explains why growth without structure leads to chaos, how poor financial visibility creates stress and bad decisions, and why systems — not hustle — are what ultimately drive profits. He also discusses the importance of leadership, accountability, and reviewing the right numbers consistently instead of relying on gut instinct.

This episode is a reset for contractors who want to stop reacting and start running their business with intention, clarity, and confidence.

• Profit problems usually come from weak fundamentals, not lack of leads

• Financial clarity is required before growth makes sense

• Systems create freedom — not complexity

• Leadership means setting priorities, not doing everything yourself

• Reviewing key numbers regularly prevents expensive surprises

• Strong foundations allow your business to grow without breaking

00:00 – Introduction to 2025 Business Essentials

05:12 – Why Growth Without Systems Fails

12:48 – Financial Clarity and Profitability

22:30 – Leadership and Accountability

33:15 – Building Systems That Support Growth

44:02 – Running the Business Instead of Reacting

https://theroofercoach.com

https://theroofercoach.com/resources

https://useproline.com

https://smasupport.us

Proline

SMA Support

👉 Download free tools and resources for roofing contractors at

theroofercoach.com/resources

Have you considered what a virtual assistant can do for your roofing business? If you aren’t sure how the process works or what the specific benefits are, today’s show lays it all out for you. Dave and John are joined by Adam Patterson of SMA Support, which provides an amazing service that is crucial to the success of many contractors. They hire, train, and provide VAs to help improve your business process and run the nuts and bolts of your business as dedicated team members. Join us to learn more!

What you’ll hear in this episode:

• John’s testimonial about what a VA can do for your roofing business (Check out Episode 373: Everything You Need to Know About Virtual Assistants with Chris Diroll.)
• Adam’s path from consulting and private equity to SMA Support
• Building a business of value by taking advantage of outsourcing opportunities
• Identify the WHY of your business
• Achieving your goals in an affordable, efficient way with a VA
• Characteristics of an engaged employee—like an SMA Support VA
• Eliminate the struggle and potential mistakes in the hiring process by employing a VA
• Repeatability structure, decision mapping, and nesting: how an SMA Support VA gets it done
• John’s perspective of Kathleen’s valuable role as the VA for Peach State Roofing
• No time to train a VA? SMA takes care of that!
• Adam’s take on managing people and offering incremental bonuses to exceptional VAs
• The role of a VA in getting reviews, getting faster payments, and providing excellent customer service
• What can a VA do for you? You, the business owner, can spend less time each week in “the drudge zone.”
• Adam’s view of what’s going on right now in the private equity world

Connect with Adam Patterson and SMA Support:

Website

Resources:

Check out this episode on our YouTube channel at @DaveSullivanRooferShow" or use this link: https://www.youtube.com/@DaveSullivanRooferShow

Be sure to subscribe, like, and comment!

Set up a FREE strategy call with Dave and get a few tips on how you can improve your business: https://davesullivan.as.me/free-strategy-call

Interested in learning more about our 1-on-1 coaching, mastermind groups, or fractional CFO services? Email me or send me a text at (510) 612-1450.

No Plan? No problem. Download our FREE 1-Page Business Plan For Roofing Contractors: https://theroofershow.com/plan

The Roofer Show’s Vetted Sponsors

Automate your follow-up process and close more sales with ProLine. Get started for FREE at https://useproline.com/?via=roofercoach. Use promo code DAVE50 for half off your first month’s service!

Have RUBY answer your phones and tee up the sale by leaving a great first impression. Use this link to get up to $150 off your first month’s service: ruby.com/roofershow.

SMA Support Services fills a need by empowering contractors to simplify and optimize their operational processes with virtual assistant services. Explore what a virtual assistant can do for your contracting business. Let SMA do the hiring, training, and onboarding. Check out SMAsupport.us (Tell them Dave sent you.)

Tune in today as Dave Sullivan dives into the different ways two roofing contractors, each pulling in about $2 million a year, run their businesses. Through some insightful discovery calls, Dave shares their unique stories, goals, and how they've set up their businesses. He really drives home the point about how important it is to have personalized coaching and a solid business plan. Dave also discusses why it's crucial to understand your financial statements and why focusing on profit is more important than just chasing sales volume. Having strategies tailored to your needs can lead to success in the roofing world, and it highlights the benefits of one-on-one mentoring and coaching services.

What you’ll hear in this episode:

• Differences between two roofing contractors generating similar revenue
• Importance of personalized coaching for contractors
• Necessity of a solid business plan, including financial understanding
• Emphasis on profit over sales volume for sustainable growth
• The franchise model versus independent business growth in roofing
• Building a roadmap for business success, including assessing current status and resources
• Lead generation strategies and the sales process
• Importance of effective communication and follow-up in sales
• Streamlining operations and outsourcing for efficiency
• Financial management and cash flow importance for business sustainability

Resources:

Check out this episode on our YouTube channel at @DaveSullivanRooferShow" or use this link - https://www.youtube.com/@DaveSullivanRooferShow

Be sure to subscribe, like, and comment!

Set up a FREE strategy call with Dave and get a few tips on how you can improve your business: https://davesullivan.as.me/free-strategy-call

Interested in learning more about our 1-on-1 coaching, mastermind groups, or fractional CFO services? Email me or send me a text at (510) 612-1450.

No Plan? No problem. Download our FREE 1-Page Business Plan For Roofing Contractors: https://theroofershow.com/plan

The Roofer Show’s Vetted Sponsors

Have RUBY answer your phones and tee up the sale by leaving a great first impression. Use this link to get up to $150 off your first month’s service: ruby.com/roofershow.

SMA Support Services fills a need by empowering contractors to simplify and optimize their operational processes with virtual assistant services. Explore what a virtual assistant can do for your contracting business. Let SMA do the hiring, training, and onboarding. Check out SMAsupport.us (Tell them Dave sent you.)

Automate your follow-up process and close more sales with ProLine. Get started for FREE at https://useproline.com/. Use promo code “Dave50” for $50 off your first month’s service!

Today, Dave dives into why having a solid business plan is crucial for roofing contractors. He chats about how important it is to know where your business is headed and the reasons behind your goals. He also talks about the key role financial statements and cash flow management play in running a successful business. If you’re wanting to write a strong business plan, Dave will give you what you need to get it done, so tune in!

What you’ll hear in this episode:

• Importance of a well-rounded business plan for roofing contractors
• Understanding the destination and "why" behind the business
• Significance of financial statements and cash flow management
• Common pitfalls faced by contractors in financial management
• Development of a mentoring program for ongoing support and accountability
• Eight essential steps to building a solid business plan
• Importance of customer service and operational efficiency
• Introduction of a free resource: the "one-page business plan"
• Emphasis on tracking key performance indicators (KPIs)
• Planning for long-term goals and exit strategies in business

Resources:

Check out this episode on our YouTube channel at @DaveSullivanRooferShow" or use this link - https://www.youtube.com/@DaveSullivanRooferShow

Be sure to subscribe, like, and comment!

Set up a FREE strategy call with Dave and get a few tips on how you can improve your business: https://davesullivan.as.me/free-strategy-call

Interested in learning more about our 1-on-1 coaching, mastermind groups, or fractional CFO services? Email me or send me a text at (510) 612-1450.

No Plan? No problem. Download our FREE 1-Page Business Plan For Roofing Contractors: https://theroofershow.com/plan

The Roofer Show’s Vetted Sponsors

Have RUBY answer your phones and tee up the sale by leaving a great first impression. Use this link to get up to $150 off your first month’s service: ruby.com/roofershow.

SMA Support Services fills a need by empowering contractors to simplify and optimize their operational processes with virtual assistant services. Explore what a virtual assistant can do for your contracting business. Let SMA do the hiring, training, and onboarding. Check out SMAsupport.us (Tell them Dave sent you.)

Automate your follow-up process and close more sales with ProLine. Get started for FREE at https://useproline.com/. Use promo code “Dave50” for $50 off your first month’s service!

Today, Dave Sullivan chats with Nick Peret, the founder of Better Boss, about the hurdles roofing contractors encounter with technology and CRM systems. Dave highlights how crucial it is to implement these systems properly and ensure the team adopts them to steer clear of inefficiencies. Nick brings up the idea of a fractional CTO, which offers top-notch tech expertise without the expense of a full-time hire. Tune in as they emphasize the importance of having structured processes, job costing, and maintaining a positive leadership attitude. This episode is packed with valuable insights for contractors aiming to boost their operations and achieve sustainable growth by effectively using technology and optimizing processes, so tune in!

What you’ll hear in this episode:

• Challenges faced by roofing contractors in implementing Customer Relationship Management (CRM) systems
• Importance of proper implementation and team adoption of technology to avoid inefficiencies
• The role of a fractional Chief Technology Officer (CTO) in providing technology expertise to contractors
• Need for structured processes and standardized operating procedures (SOPs) in business operations
• Significance of job costing and tracking financial metrics for profitability
• Strategies for scaling a business sustainably while maintaining profit margins
• The impact of technology, including AI and automation, on enhancing business operations
• Importance of adapting to changing customer interactions and expectations
• Risks associated with delayed payments and cash flow challenges in the storm work sector
• Value of mentorship and expert guidance for contractors seeking to improve their business practices

Resources:

Connect with Nick Peret and Better Boss! 

Better Boss

Facebook

YouTube

Connect with Dave and The Roofer Show!

Check out this episode on our Youtube channel at @DaveSullivanRooferShow" or use this link - https://youtu.be/N7F2wJVbfwk

Be sure to subscribe, like, and comment!

Set up a FREE strategy call with Dave and get a few tips on how you can improve your business: https://davesullivan.as.me/free-strategy-call

Interested in learning more about our 1-on-1 coaching, mastermind groups, or fractional CFO services? Email me or send me a text at (510) 612-1450.

No Plan? No problem. Download our FREE 1-Page Business Plan For Roofing Contractors: https://theroofershow.com/plan

The Roofer Show’s Vetted Sponsors

Have RUBY answer your phones and tee up the sale by leaving a great first impression. Use this link to get up to $150 off your first month’s service: ruby.com/roofershow.

SMA Support Services fills a need by empowering contractors to simplify and optimize their operational processes with virtual assistant services. Explore what a virtual assistant can do for your contracting business. Let SMA do the hiring, training, and onboarding. Check out SMAsupport.us (Tell them Dave sent you.)

Automate your follow-up process and close more sales with ProLine. Get started for FREE at https://useproline.com/. Use promo code “Dave50” for $50 off your first month’s service!