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The BRUTAL Truth About Roofing Sales Careers

The good, the bad, the ugly, and the demons.

I’m going to share the BRUTAL truth about life in roofing sales.

The truth is we ALL face some challenges and mid-season burnout in this business, regardless of whether you are:

  • A seasoned veteran
  • A manager running a team
  • An owner

So, this is for anyone who is:

  • Interested in roofing sales 
  • Questioning whether they should stick with roofing sales

Whether you’ve been at this point or you know someone who is right now, read on and share this blog. I hope that it’s inspirational and helpful.

First, though, I want to say welcome or welcome back. My name is Adam Bensman, The Roof Strategist. I am really excited to have you here.

Everything I do here — and on my YouTube channel, on my podcast (on Apple and Spotify), and in my programs — is designed to help you and your team smash your income goals and give every customer an amazing experience.

To support you on that journey, I invite you to download a free copy of my Pitch Like a Pro roofing sales training video library.

Now, let’s talk about the brutal truth about roofing sales careers. I’m going to:

  1. Talk about the positives and why people get into roofing sales
  2. Dig into the more negative stuff people generally don’t talk about

Why Roofing Sales?

What excites me so much about the opportunity in the roofing sales industry?

I love roofing sales because anyone — regardless of their age, background, education, or experience with sales or even the roofing industry — can come into this industry and ABSOLUTELY transform their life.

It’s truly a level playing field for absolutely anyone.

And this industry changed my life.

I used to be a massage therapist earning less than $20,000 a year, and roofing sales COMPLETELY changed my life.

That’s why I run my YouTube channel and this blog — it’s to help you do the same. And it’s why I love roofing sales.

Now, what most folks do NOT prepare you for is what you’re actually going to deal with when you get into this business.

We sell the BIG idea — that you can make $100k to $200k a year. Again, I know some people earn way north of that, but $100k to $200k is reasonable within your first year.

We’re also sold on this grand vision of just going out and knocking on doors. It’s the easiest way to make money.

And the reality is VERY different than this dream that’s often sold or that lures us into roofing sales, whether or not we’re being sold on it. In fact, some of the easiest people to sell to are salespeople, and I’m guilty as well.

So, that’s why I love roofing sales and what tends to attract people to this business.

Now, let’s break down the reality, with some brutal truth about what it’s really like to have a career in roofing sales.

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Roofing Sales Truth #1: It’s Simple, Not Easy.

The first brutal truth of roofing sales is that it IS incredibly simple, but it is absolutely NOT easy.

So, many people get into this business, thinking, Hey, it’s one of the easiest ways to make a living.

You may agree or disagree with that, but the idea is that the concept itself is very simple. The sales process and the sales cycle are simple. Once you learn it all, it’s very simple.

Still, simple is INCREDIBLY different than easy.

Easy means anyone could do it. If it were easy, everybody would do it. And the truth is most people end up falling victim to the second brutal truth, which is wanting to quit.

Roofing Sales Truth #2: You WILL Want to Quit.

It’s true. At some point, you’re going to feel like quitting.

Owners, I know you you’re thinking:

Yep. I feel like I built my own prison cell.

I want to quit because of the personnel issues, the cash flow stuff, the angry customers, and ALL of the headaches.

There are times when we WILL want to quit. That’s normal.

If you’ve ever questioned it, it means you ARE doing the right thing. It means that you’re on the roller coaster, the journey, that roofing sales takes you on.

Now, most people quit too soon, like a gentleman who sold for me named Jordan. He struggled for 8 weeks and ended up with like no sales, meaning no income. Then, he hit this hot streak. Things picked up like wildfire, and he landed the equivalent of about $50k in commissions. But he still left to pursue a desk job for a salary.

Like Jordan, too many people end up quitting roofing sales too soon. They quit before tasting the success.

There’s another young gentleman, named Kaleb — shout out to you, Kaleb! I interviewed him on my YouTube channel right before he turned 21. When he got into roofing sales at 20, he had month after month of rejection, signing deals, getting denials, and not getting any traction.

Now, very quickly, most people in that situation would think, Hey, it’s not working. I’ve given this three months, and now I’m out.

Not Kaleb. He stuck with it. And not only did he succeed, but he also earned his first six figures right after turning 21. Now, he’s leading a team, and he’s absolutely kicking butt! And you can tell his life has changed. He’s SO incredibly happy.

So, again, wanting to quit roofing sales is entirely normal. It’s part of the roller coaster.

Roofing Sales Truth #3: Face Your Inner Demon.

At some point in this business, you WILL be forced to face is what I call your “inner demon.”

Now, everyone has an inner demon. In fact, I’ve done an entire video on How to Conquer Your Inner Demon because any of us can be our own worst enemy.

And, in this business, we are forced to confront ourselves and, specifically, our:

  • Weaknesses
  • Conflict avoidance
  • Communication concerns
  • Discipline
  • Motivation
  • Confidence

Any or all of these factors can be the BIGGEST obstacle standing between us and our income. And this demon is not pleasant to fight. What it does bring to mind is this quote from David Goggins:

If you want peace, you first have to go to war with yourself.

Well, in roofing sales, our inner demon is that one personal roadblock that we have to grow through and lean into.

Example: There’s a gentleman who I’ve served, a military veteran who served in Iraq, under some of the most horrible conditions and in some of the most dangerous places. He’s been in combat, where he never once skipped a beat. In roofing sales, though, he goes to knock on doors, and he freezes up, crippled with fear. So, he’s fine when he’s facing real external threats, but the minute he’s dealing on an interpersonal level, he freezes.

Inner fear makes us freeze up.  As opposed to an external fear, the inner fear can become larger than life.

So, you need to be ready to lean into that discomfort because pretty much no other career is going to force you to do that.

And that’s one of the reasons people quit.

Roofing Sales Truth #4: Protect Your Mindset.

Besides your inner demon, you will have a time when your mind is poisoned.

What do I mean by poisoned?

If you’re seasoned in the business — or if you’re a manager or owner — I’m sure you’ve had this happen where you’re on a hot streak, everything’s going really well, and then suddenly, we hit this stride of negative customers, saying things like:

You’re a sleazeball.

If I wanted to buy from you, I’d call.

Get a real job.

You’re a scam artist. You’re a con artist.

You’re a total scumbag.

We start hearing all sorts of negative things from people. When that happens, we poison our own minds because we internalize all this outside negative chatter.

It’s no different than a young child being bullied about their weight, their looks, or an impediment. It poisons their own narrative. They tell themselves things like I’m too stupid or I’m not good looking enough or whatever.

So, it’s important to protect your mindset in order to succeed in roofing sales.

Roofing Sales Truth #5: Customers WILL Drive You Crazy.

I guarantee that, at some point, your customers WILL drive you crazy.

I say that because our customers are both the BEST part about roofing sales and the HARDEST part of the job.

With customers, we can have conflict and angry folks. It happens, and it leads me to the next brutal truth.

Roofing Sales Truth #6: Things Will NOT Always Go As Planned.

You just need to know that things will NOT go as planned. By the way, I’m kind of a perfectionist. I want to give amazing service to the people I serve. It’s our core value at our companies — to create amazing experiences.

And things do NOT go as planned in roofing. In fact, when you do a project:

  • Things can break as you’re pulling tons and tons of debris off a roof
  • Coordination between your supplier and the crews can go awry

When things don’t go as planned, customers get upset. Again, it’s just going to happen. That’s why I tell folks this:

Listen, it’s not if, it’s when.

This is construction, and there’s a ton of debris coming off and going on.

I just want you to know that if things don’t go right, we’re going to take care of you.

When you’re new, you have this tendency to want everything to go perfect. It can be kind of a delusion because it just won’t go the way you envision every time.

So, don’t over promise, and remember, things do NOT always go as planned.

Beyond the Brutal Truth: The Real Value of a Roofing Sales Career

Now, this last piece is the most important.

Roofing sales is personal development in disguise.

I’ve been saying this for years because there’s almost no other industry in which we can literally change what we say or what we do and earn an extra $5k, $10k, or even $20k per month.

It’s all through personal development, meaning your:

  • Communication
  • Organization
  • Motivation
  • Discipline
  • Sales skills
  • Objection handling
  • Written communication (including how you sell via email and text)

Anytime we make improvements by becoming more confident, communicating better, or managing our time better that carries over into sales, resulting in personal development and more income.

Wrapping this up by circling back to the beginning, this is one of the reasons why I love roofing sales.

We get to gamify our own personal development.

And I’ll be the first to tell you I don’t really care much about roofs, like roofing products. I never thought, When I grow up, I want to be in roofing or I just love shingles!

That stuff doesn’t matter to me. But it’s the way to:

  • Give customers an amazing experience
  • Solve a problem that many homeowners have

I know I can do it better than many other people, and my reward for doing that really well is earning a really handsome living.

But the best part about it is I get to become an even better version of myself each and every day because I’m challenged.

So, that to me is the real beauty that can help you ride through the wave of these brutal truths about roofing sales.

Recap: 6 Things No One Tells You About Roofing Sales

Let’s wrap up with a quick summary.

  1. First roofing sales is simple. It is NOT easy.
  2. You WILL want to quit. That means you’re riding that rollercoaster of ups and downs, so buckle up. It’s a wild journey, and your neck will indeed get ripped around.
  3. Face your inner demon. You’re going to have it. We all have one.
  4. Protect your mindset. Do NOT let anyone poison it. If you start telling yourself what other people are telling you, that’s when you know your mind has been poisoned.
  5. Customers are going to drive you nuts, so kill them kindness. They’re the BEST and the most challenging thing. And the more skills you develop to get through that process, the better off you’ll be.
  6. Remember, things are NOT going to go as planned. It’s construction, and it’s roofing. So, setting those expectations is going to help everyone ride the wave.

So, there you have it, the brutal truth about this business. That’s what you can tell someone to prepare them for the realities of life in roofing sales.

Get More Roofing Sales Strategies, Scripts, Tips & Videos

If you want more on any topic in roofing sales, you’ll find it in my all-in-one sales training, sales strategy, and sales system, the Roofing Sales Success Formula & Complete Sales Strategy.

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If you have questions, just call or text (303) 222-7133 for more info or a private demo.

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Thanks for joining me, and I look forward to sharing more with you in the next blog.