What to Expect in Roofing Sales: 5 Things I Wish I Knew When I Started

Adam Bensman’s YouTube video outlines five expectations for newcomers to roofing sales: (1) it will be harder than anticipated; (2) expect 1–4 months before commissions arrive (longer for insurance-driven markets); (3) setbacks and cancelled deals are common during the learning curve; (4) friends and family will often doubt the career early on; (5) you will frequently wonder whether to continue. Bensman frames roofing sales as "personal development in disguise," arguing that personal growth precedes life-changing income. The video includes anecdotes (Eric, Caleb), a cautionary fable, and CTAs to a book and free training.
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What to expect in roofing sales if you're brand new that no one's telling you. Well, that's what I'm going to lay out in this video. There are five things for you to expect and I want you to think of it like a roadmap because one of the main reasons that roofing sales has such high turnover, which I'm sure you've either observed or heard about seeing the fact that I estimate two out of three reps will quit or get fired in their very first year is often due to not knowing what to expect. In fact, when they were sold and excited about which is this crazy high earning potential, fast paced environment, fun way to make a living, and then what they experience is different. Like the classic expectations versus reality. Like that didn't work out. And when you know what's coming, it won't come as a surprise. You won't feel blindsided. You're going to be prepared to ride the wave. So you're like, I knew this would be here. I can push through. This is normal. And so many people think that it's not normal or they're not normal. So let's shake out these five things starting right now. Actually, before we do, if you're new or if you're maybe a manager, owner training a team, share this video with the people on your team who are new who need to see this. All right, now, let's rock and roll. Roofing sales is personal development in disguise and the reward for growth is life changing. I hope my content helps you create a richer life and bank account. Hey, before we get into this list, I want to share a story that explains why roofing sales is so challenging and why there's such high turnover. Now this is a fable. I don't know if this is a true story, but the message rings true. So let's jump into it. Now this company, they supposedly ran a hiring end that said earn $200,000 a year shoveling chicken poop. And naturally applicants came, flooded in, flooding in like, oh my gosh, that's so easy. All I have to do is shovel chicken poop. So they ran a group interview and there are guys and gals like crowd around this table so excited to make life changing money. And the gentleman, he kicks off the interview, says, hey, thank you so much for coming in. I'm so excited to share the opportunity with you so you can make life changing money with our company. And I want to share the good news first. You don't even need to shovel chicken poop. All you need to do is go knock doors. And just like that, everybody who applied got up and left. Why? Because they were more willing to shovel poop than to deal with their own poop, if you catch my drift. See, roofing sales forces you to face your own inner demons and challenges that you likely have not faced in other careers. You'll experience the highest of highs, the lowest of lows in the same week, in the same day and in the same hour. You'll be carrying your baggage and personal baggage from home, the fight with your spouse, the family member who's going through cancer treatment, going through a divorce. And you have to bring all this to work and kind of like compartmentalize it. Even though it's impacting your sales, you're going to deal with rejection over and over and over again, days on end that you feel like you've worked without any results because you're commission only or heavily based on commission. And for that reason, people don't last. I know you saw in my intro that roofing sales is personal development in disguise. And the more that you grow, the more that you earn. And it takes a very special person to have that level of grit, discipline to push through all of this. And the special people who do, they reap the reward of life changing income. And I just want to start off this video right before we get into the list that if you want uncommon results in life, which is uncommon success in uncommon levels of income, you have to be willing to do uncommon things that most other people aren't willing to do. That's why so many people don't last. So let's rock and roll. Starting with number one on the list, expect it to be harder than you thought. Now, there are people who experience wild success out of the gate, like Eric right here. Eric's guy, Eric went through training on my system and on day one in Houston signed eight deals. But is this going to happen to everybody? No, it won't. Could it? Yes. But I don't want you to expect that. I want you to expect that it will be harder because roofing sales is simple but not easy. And these are very different. And folks like me who've been in a while, folks like maybe you're the owner, manager, who's supporting you, they've been in this and they often forget. We often forget the beginner's mind of how much we have to learn, even though it's simple. But there's a lot to learn. So expect it to be harder. And that way, if it is easy, you're like wow, this is a surprise. But if it is hard because it took me by the way, six weeks to make my very first sale. So imagine going out six weeks straight, knocking doors, talking to people, rejected, rejected, rejected. Six weeks, if not one ounce of hope towards making a dime and sticking through it. And I'm not the only one. In fact, Caleb, I did an interview with Caleb and we're going to put a link to that video up here. And Caleb experienced setbacks for months on end to the point where most people would have packed up their bags and left and, and he pushed through it. And by 21 years old, just shortly after his 21st birthday, he made his very first six figures. Caleb ended up growing within the company, which you don't see in this video, running a team and now runs his own company. And just expect it to be harder than you thought. Now let's jump into number two. Expect one to four months until money starts rolling in. Now if you're selling with a retail company which is homeowners paying out of pocket electively to replace the roof, the sales cycle is often quicker in getting commissions is often quicker. But if you're in a market, let's say like Texas, Minnesota or Colorado, that is heavily driven by insurance claims or storm damage, those deals can take longer to process because you have to sign the deal, meet with the adjuster often and then maybe do some supplementing things that the insurance company missed and you're submitting paperwork back and forth, then you're building the job, then you have to invoice the insurance company to release the final funds, then collect payment from the homeowner. Then you get paid and often commissions are paid once the company gets paid. So that sales cycle and timeline can last one to four months depending on the insurance carrier and how that process goes with your company. So don't be alarmed. A lot of people are like, I have no money rolling in. Expect it, expect that you won't. But remember stability and security and high income. You have to pick one. And if you're willing to do this short term sacrifice, the money that you make creates that stability via high income. So just expect it, it's normal. Number three, setbacks and frustration. I feel like this is a rite of passage for new salespeople where they'll like sign deals and homeowners cancel. By the way, it's cause they're having learning curves. They're either overselling or miss selling. And sometimes these setbacks are like deals that they thought they were going to have but they had this stink of desperation because they were new and needed the commission. And the homeowner smelled what, what's known in the industry as commission breath. You know, people really wanting the sale. And they come across as pushy, sleazy or salesy, even though they don't mean it. And homeowners don't buy from them or maybe they're in the wrong neighborhood. So the deals that they signed if they're selling storm damage end up getting denied by the insurance and they lose faith in what they're doing. So just expect a boatload of setbacks and frustrations. It is part of the learning curve and it is like to be expected as a rite of passage. As you figure this stuff out, do not take it personally. It is just a very common, very normal thing. And go watch that interview with Caleb to hear his story and the level of persistence that he had and how it has paid off to change his life. Number four, doubt from others. Expect that your friends, family, and even your spouse or significant other will doubt your career. They're going to see the very long hours you're putting in, the very low return in the very beginning. And they're going to say, hey, should you be doing this? Is this right? Because remember, at the end of the day, it's not that they doubt you, it's how they express this doubt because they love you. And just like a parent loving its child, people don't want to see their child suffer. So they're willing to do almost anything to alleviate the pain and the struggle from their child. And the same is going for your friends, family and significant other. What they want is for you to have stability and security and to do well. And when they see you struggling and putting in long hours and working seven days a week and having these setbacks and coming home depressed and frustrated and angry, they want to just immediately relieve that pain. And they're like, hey, go do something else. You don't need to go through this. Life's too short. But what they want is the quick fix to just get you that stability and security. And you almost have to say, hey, I love you. I get that. But all I need to do is push through these few months and then I can create that stability and security through this high income. And Adam told me to expect all of this. This is normal. Okay? By the way, share this video, watch it with your spouse, significant other, or even share it with family. Number five. You will wonder whether or not you should be doing this. This is incredibly common. In fact, I've spoken on stages all across the United States from Pennsylvania to California, Washington, Seattle, Florida, and pretty much everywhere in between. And when I have asked people, I've surveyed them, I said, hey, raise your hand if you've thought about leaving roofing sales. It is incredibly uncommon that people don't raise their hand. It's totally normal. And it is especially normal in the very beginning when you're going through these setbacks, when you don't have money rolling in, when your family is doub you and you begin to doubt yourself. It is natural to wonder, should I be doing this? Should I go do something else? And as those thoughts come up, just know it is normal. Even the most successful people have had those thoughts. So quiet them and stay focused on your goal and stay focused on your why. And if you need help on establishing your goal and your why in navigating the mental and emotional battlefield that is roofing sales, grab a copy of my book, the Roofing Sales Survival Guide. Now, I told you at the end I had a bonus and that is this. You will experience life changing results. Now, I don't mean this in terms of life changing, just on the money side, your life will truly transform. This business is personal development in disguise. And today I am nowhere near the person that I was in 2011. In fact, you wouldn't even recognize me in 2011. I was a person who lacked confidence. I may have come across as confident because I had a sense of humor and I like talking to people, but I was miserably uncomfortable. I was someone who was horrified of conflict. I had to face my own inner demons because I grew up in a household where it was emotionally volatile and my role was playing peacekeeper. I tried to keep everything safe and I just at all costs didn't want conflict. So when I had to start knocking doors and frustrating people and having people yell at me, and when stuff went wrong on production like it challenged me every day, I cannot even begin to express the level of discomfort I had. And through this business I have been able to develop new skills, be a better version of myself and be forced to face my own inner demons to conquer the negative self talk the self comparison and be a new, better version of myself. And each time I did, my income followed because I was able to serve people better and navigate situations that in the past would have crippled me. So you can expect a complete life transformation, both personally, which this is the most rewarding in my opinion and what follows. As you transform personally, your income grows with it. It doesn't go the other way around this industry. I love And I'll tell you first things first. I don't care about roofs. I don't give two flying you know what's about roofs? They mean nothing to me. I'm not passionate about it. I but I'm wildly passionate about this industry and the life changing results that it can provide to you. So I hope this video helps you navigate the unknown because now you know exactly what to expect. All right, if you want more like this, jump into my free training center right now. There's no catch and I have binge worthy content to support your journey in roofing sales. And if you're an owner or manager and you want to support your team, you can join me in the trenches along with the industry's top leaders like Daeshawn Bryant, John Cenac, Jim Alleen and Cody Landles to arm your team with the ultimate toolbox. I'd love to see inside it's application only, but click below to learn more about the Roofing and Solar Reform Alliance. Hey, just because our time here is about to wrap does not mean your and my time has to. So right after this, you're going to see a playlist called how to make $100,000 in roofing sales. It is the perfect playlist for the new salesperson to learn the daily habits, how to make their first sale, and much, much more. Jump into that and I'll see you on the next.










