Lessons From a Rookie Roofing Salesman

Rookie Roofing Sales
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Rookie Roofing SalesA 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.

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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?

About The Author

Mike Coday

Mike is a retired youth pastor turned marketing consultant, author, speaker, sales trainer, and sentimental family man. His expertise is internet marketing...and bad Dad jokes.

Facebook Comments


  • chase

    Reply Reply October 23, 2012

    Hey Mike first I want to thank you for all the advice your sharing. I am 21 years old and was approached by my farthers friend which handed me a job. Ive been working for 2 months now and have sold 4 jobs. I feel like I’m doing pretty well for this storm being 4 months old but I still don’t know if I should stick this out. The company I work for seems like a well ran place. The owner is a very nice person. But the problem I’m having is no one knows if they can trust a “kid”. Any advice on how I can step it up and make home owners look past that I’m young? Thank you for your time in advance.

    • mike

      Reply Reply October 23, 2012

      Hey Chase,

      Congratulations on your 4 sales.

      That’s 4 more sales than most guys get who try roofing sales. You’re doing great. I suspect you have natural sales ability and a lot of hustle in you. Well, just the fact that you’re reading these articles, trying to get better at what you do, tells me that you’re the type of guy who can make it work.

      Chase, here’s the first thing I want you to realize… whether you’re 21 or you’re 41, roofing salespeople all have the same challenge… how do I get my prospects to trust me? It never changes.

      The fact that you’re 21 is a big problem for some prospects. You’re never going to win them over anyway. However, the fact that you’re 21 is also a big advantage too. You’re young, fresh, eager, hard-working, honest, willing to go the extra mile… all things that people like.

      Since you can’t be 41 (no matter how hard you try), you may as well work with what you’ve got.

      Number two, not everybody in your company is 21. You need to remind your prospects that your job is to take care of them and your roofing company will take care of their roof. Tell about your father’s friend. You say he’s a nice person… explain that to your prospects. Tell them about the crew and how long they’ve been in roofing. This is called “borrowing credibility”. Because of your young age, people may not perceive you as having credibility, but that doesn’t stop you from “borrowing” it from the company you represent.

      Finally, 4 different people have bought a roof from you. 4! That’s really good (unless they were your Mom, Grandma, Aunt and Uncle). Maybe one or two of the were, but probably not all 4. Ask yourself, “WHY did they buy from me?”

      What did those 4 people see in you? How did they justify making the purchase? What did they say?

      When you come up with an answer to WHY, you’ll know HOW to sell your next 4 roofs.

      What other questions do you have Chase?


  • Becky Jones

    Reply Reply April 3, 2012

    Wow! So glad I found you from just doing a general Google search. I was a special education teacher for 11 years and decided I couldn’t and didn’t want to do that forever,so here I am a rookie roof saleswoman. I must say I did raise a few eyebrows by choosing this line of work, but I’m giving it my all and really believe a woman can prove very successful in this business. I would love to hear any advice you could offer on being a woman in roofing sales.

    • mike

      Reply Reply April 4, 2012



      Both of my parents were special ed teachers. Thank you for your years of service to the kids who needed it the most and congratulations on your new career move.

      So, being a woman in roofing sales is actually a very big advantage because the traditional family where the man makes all the decisions is a thing of the past.

      You are going to find a lot of women who would prefer to with you over a man. Even men prefer to work with women because there’s often a higher level of trust there.

      We have a young lady in her 20’s along with her boyfriend who solicit roofing appointments. She always sets more appointments than he does. People are just more comfortable opening their door to a lady.

      That’s your big advantage… trust.

      Obviously, you’ll have disadvantages, but we all do. The trick is to set your mind to focus on your advantages and walk away from your weaknesses. Don’t dwell on what you can’t do. Focus on what you can do… and you can get in front of a lot of people to offer your services.

      You’ll get plenty of practice with your presentation. Get it down to an art. Know your objections and learn how to overcome them.

      Roofing sales is repetitive. Get good at the fundamentals… prospecting, presenting and following-up.

      I’m sure you’ll run up against specific questions as you move along. Be sure to come back and let me know what’s going on. I would love to help you.


  • James

    Reply Reply February 14, 2012

    amazing site. selling real estate for 5 years and roofing for the past 2… i would say you’ve got it pretty well pinned here. keep up the good work! i really enjoyed myself reading this, it is very motivating to know others have the exact same concerns and feelings… Good Vibes.

  • Rusty

    Reply Reply September 18, 2011

    Mike, thank you for taking time to share your insight and knowledge! This is great info for a rookie as well as any pro.

    Curious, how do you feel about wearing a safety vest with an Id badge around your neck?? Is this just flat out con man BS or do you think it may have some credibility? I read your article about Axe murderers and completely agree with you. However, you can push NLP in the other direction, Act the Part, Look the Part,and Be the Part. Same concept as truck v car? Any thoughts??

    • mike

      Reply Reply September 18, 2011


      Gotta admit I’m not a big fan of the orange safety vest with the i.d. badge hung around your neck. That said, if it is the law in your area, and it is the law in many areas, you have absolutely no choice… wear them with pride.

      However, if you aren’t required by law to wear the vest and badge, I would strongly recommend you stay away from ’em. Here’s why… I don’t like what the image represents. Makes me think magazine salesperson or miracle driveway cleaner guy. Outside of Axe Murderer, those are the last images you want your prospect to get when they answer the door. My opinion is that every “costume” communicates a message. As roofing salespeople, we want the message of our “costume” to be #1 Credibility and #2 Authority.

      You bring up NLP, and that’s very interesting to me because you know that the meaning of any message is whatever the receiver perceives it to be. There may be instances when the safety vest and i.d. badge are perceived as Credibility and Authority, but overall I would tend to believe that they would be perceived as anything but that. There’s possibly one segment of our population where this costume might work exceptionally well, but I’ll keep those demographics to myself. You may already know which segment I’m thinking about.

      Very interesting and insightful question Rusty. Thank you for sharing your thoughts tonight. Have you joined us over on Facebook yet?


  • Amanda

    Reply Reply April 24, 2011

    Right now I am a rookie roof saleswoman and I am loving all the info you are providing…this site is so incredibly helpful and motivating!

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