Lessons From a Rookie Roofing Salesman

By Mike Coday •  Updated: 03/29/21 •  5 min read

A long time ago, in what seems like another life, I was a rookie roofing salesman.

I know – roofing has a reputation for being a slimy business. Have a hailstorm, hurricane or a tornado and all the roofers within 300 miles of your house will descend on your neighborhood like frogs in Egypt.

Roofers will knock on your door, call you on the phone and litter your door with flyers until you finally make a decision.

The best way to get rid of a roofer is to get your roof replaced… then you won’t see them again… ever!

Hopefully, that isn’t how you do business. I’m sure it’s not. Otherwise, you wouldn’t be here reading tips on how to make more money selling roofs.

#1 Loser

It was back in my rookie year that I learned my most valuable lesson.

I was the #1 roof salesman in my office according to the number of contracts signed, but I was ranked #20 in terms of dollar amount. In a few short months, I had managed to sign over 50 contracts. Meanwhile, the top dogs in the office only had 20-30 contracts, but were making 3x as much money.

So, what was the problem?

Well, I was signing up small roofs. I was comfortable approaching people who lived in homes that looked like the home I grew up in (modest). Nice people, salt of the earth, but their roofs were tiny compared to the jobs the top dogs were signing up.

I had it in my head that I could never talk to the people that lived in those big, nice, beautiful neighborhoods. I was convinced they wouldn’t want to talk to me.

Sell Twice As Much – Make 1/3 Less

For over a year, I had to sell twice as many contracts to make 1/3 as much money. One night, I was hanging around the office when one of the top guns asked me, “Mike, why don’t you go after the bigger jobs?” I had to admit, I was afraid.

I didn’t grow up with a lot of money. My folks were both Special Education teachers… not exactly banging the bucks! I explained to Mr. Top Gun that I had no clue how to interact with the rich and affluent. He then rattled off a well-worn phrase. One I’m sure you’ve heard before:

“They put their pants on one leg at a time just like you!”

And there you have it!

You’ve heard it said before, but that night it really resonated with me. At the end of the day, people are just people.

The people on the other side of those doors you’re knocking have the same fears and hopes as you do… regardless of how nice their neighborhood is.

BONUS: Hope vs. Fear

It has been said that there are only two way to sell something. Either, fear of loss or hope of gain. I’ve personally found that fear of loss is much more motivating.

Hope Is Fleeting

By the time you hit your early 30’s, you’ve accepted that most of the things you hoped for in your youth are probably not going to happen. As the years go by, it takes less and less time for hope to fade. Those that can hold out hope for an extended period of time are a special breed.

Fear Will Haunt You

Fear never goes away! It goes with you to bed at night. It will whisper in your ear throughout the day. Fear will stalk you, taunt you and lie to you.

You’ll beat fear back and it will show up the next day ready to tackle you from another angle. That is exactly why fear of loss is the greatest motivator in sales.

If you want to sell to the rich and affluent, find out what it is that keeps them up at night. What do they think. What fears are being whispered in their ear. Find out what gives them ulcers. Show the rich and affluent that you understand what their fear is and you’re in the door talking business.

Fear The Competition

Almost without fail, the rich fear their competition. Who is their competition? Maybe its the Jones’ down the street. Could be a brother-in-law or a buddy from college. Sometimes it is the lady driving a brand new Cadillac Escalade who lives around the corner. Regardless of who, they’ve worked hard for their status. Standing out from the crowd and among their peers is important.

My experience is that the rich and affluent are generally consumed with thoughts of who might be doing better than they are. Again, that’s not always true, but I’ve found it to be generally true.

Sometimes they’ll be so consumed with keeping their status that they’ll have nightmares about someone taking it all away or diminishing their stature. While I doubt they would admit it, they spend a lot of time figuring out how to protect what they have.

You Have To Remind Them

When you go into a nice neighborhood, remind your prospects what they have to fear by not signing up with you. How will their decision to not make a decision diminish their status, keep them from standing out or appear to be less than what they want to project to their competition?

If you do this right, they’ll sign your contract because you’ll help them keep what they’ve worked so hard to get.


P.S. Join the conversation… what was your biggest lesson from selling roofs as a rookie?

Mike Coday

Mike started selling roofs in '95 while working as a youth pastor at a small church in North Texas. A decade later he transitioned to speaking at industry conferences and training outside sales teams. Today, he works exclusively as the premier consultant to roofing company owners who are driven for growth.