Don’t Let the Puppy Pee on the Carpet – Guest Insight from Casey Brown

September 26, 2025

I’m always looking to bring valuable perspectives to our roofing community.


My friend Casey Brown, Founder of Boost Pricing, specializes in helping businesses strengthen their pricing strategies. She recently shared this piece, tailored for roofing contractors, and it’s too good not to pass along.

Don't Let the Puppy Pee on the Carpet

Casey Brown, Boost Pricing


Let's talk about the "foot in the door" or "land and expand" approach to pricing: offering discounted pricing to entice a prospect to leave their current roofing contractor and give you a shot. You tell yourself you'll raise prices later, once they're hooked on your quality and service. But let's be honest: it's like adopting a puppy and saying, "Sure, it's fine if you pee on the carpet now. I'll teach you to go outside later, once we've bonded."


Spoiler alert: later is a long, hard slog of un-training bad habits you allowed in the first place.

Starting a customer relationship by underpricing your roofing work trains them to expect it. You're signaling that your excellence comes cheap, and untraining that entitlement can take months or even years.


This isn't just about lost revenue and profits; it's about the long-term erosion of your pricing power. The moment you cave to a discounted "first roof," you've set a dangerous precedent. You've handed them the keys to the discount kingdom, and now you have to figure out how to lock the gates.


I know what you're thinking: "But commercial roofing is all RFPs and sealed bids. The property manager has three bids on their desk, and lowest price wins." Yes, sometimes. But not always. Even in the bid-based world, there are ways to compete beyond racing to the bottom.


The best way to avoid a bad habit is to prevent it from forming. If you're excellent at what you do, your pricing should reflect that from the beginning. By focusing on outcomes and the unique value you provide, you create a foundation for mutual respect and value. Otherwise, you'll spend years cleaning up messes you could've avoided.


Is it easier to get a building owner or GC to switch contractors with a discount? Sure, sometimes. But is it better? Not unless you have no other viable options. Too often, roofing contractors reach for the discount lever because it's the easiest one to pull, mistaking it for the only option. That giant, obvious lever blocks the view of more creative, less costly ways to win the prospect's business.


If you think discounts are your only shot, lock yourself in a room with a whiteboard and no distractions. Don't come out until you've identified at least five ways to earn a prospect's trial without discounting. Discounts are easy, but they're incredibly costly. Do the harder, more strategic work of crafting other ways to convince the customer to try you out.


When five bids hit the desk and yours is 10% higher but clearly demonstrates you understand their specific needs, you'd be surprised how often "lowest bid" suddenly becomes "best value."


Pricing isn't just about numbers; it's about training expectations. If you teach customers that you discount to get in the door, don't be surprised when they try to keep you there. Confident, fair pricing from the beginning sets the tone for a partnership rooted in a fair exchange of value. That's a precedent worth setting.


Shared with permission from Casey Brown, Founder of Boost Pricing.



📌 Connect with Casey:
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