If I Started in Roofing Sales in 2026 With $0, I’d Do These 5 Things

Here are the top 5 things that I would do differently if I started over in roofing sales in 2026. My name is Adam Bensman. Welcome or welcome back. Let's jump right into it. Number 1 on the list, I would record everything. With AI tools, these options are nearly endless. Now there's industry-specific software for door-to-door sales and home improvement sales. And if your company has those, use them. If not, you can record your own and just make sure it's legal in your state. Now, there are tools like Otter, for example, that are run on an app on your phone, will record, transcribe, and summarize all of the sales conversations that you're having throughout the day. In doing so, you can grab those transcripts and use them for these 3 reasons or use cases. Re— uh, use case number 1 is to stay organized so you can follow through on everything you promised. Number 2 is to use your transcripts for sales coaching feedback. To discover why people reached out, what their biggest questions and objections were, to analyze talk time on the transcript and get professional coaching advice by simply a prompt saying, act like a professional sales coach, analyze my transcripts and tell me what I can do better. These are just a few examples. You can get really specific on trying to analyze why you didn't close the sale and what you could have done differently to give you suggestions for closing techniques. You can prompt it to be more aggressive or less aggressive, which is my preference. These are infinite possibilities for you to extract this data. And then the last thing is to use it to help you generate social media content, which I'll be covering here shortly. You can pull out prompts for video ideas. You can pull out and have it write social media posts based on your conversations. A lot of this and more I've engineered and given away prompts in the Roofing and Solar Formulines. But I'm sure that you can take this concept and run with it. Now, number 2 on the list that I would do differently if I started over is I would build a strong personal brand on social media. Now, a few things that I want to address. A personal brand is not showing off to your fellow roofers on the monster deals you're closing and the stuff you're blowing your money on. What I want you to think through is becoming the neighborhood trusted roofer that is known and associated with providing valuable information. You can grab your phone and as you leave a customer's house, while you're walking down the sidewalk back to your truck saying, hey, Peggy called me because— and then explain what was going on. Or Peggy just asked me this question, or Peggy chose to hire us because of this. You can again grab your transcripts to produce social media posts. You can put up pictures of your homeowners smiling in front of their new roof, holding your yard sign. You can ask them to share it on social media. And say, hey, this would really help me help other people that, you know, that might need a new roof. There's almost infinite possibilities to build your personal brand and start to get known in the social networks within your neighborhood. Just make sure that you're providing answers to people's questions and making it fun. All right. Number 3 on the list, I would get highly involved with my community. I recently did an interview with Dan Walrack. He actually came in and ran a session inside RSRA. And if you have never heard of Dan, he has been doing roofing sales for 27 years and his best year in business was $18.5 million personally of residential sales. It's mind-blowing. And when you start peeling back the curtains to figure out why and how he did it, it was largely based on his community involvement. And this community involvement is things that like Taylor Spears, a fellow member of RSRA, has shared on the channel how they're doing dugout roofs for free, which again is a couple of square in exchange for permanent plaque. People are volunteering to work the concession stand at local football games for the, the high schools. So getting involved in the places that matter to you will help you get known and build a relationship-driven referral network. Now, number 4 on the list. I would turn into a tech guru. You know, tech before was less important. We showed up, we knocked on a door. I remember when I got started in 2011, I'm going to sound, by the way, for a minute like the grandpa that says, I walked uphill to school both ways in the snow, right? So when I got started in 2011, there wasn't, you know, we were still hand-measuring roofs. We were using a fax machine to send in our material orders and like in our filing for depreciation on our insurance projects. Like it was such a different animal than it is now. And the reason I'd want to turn into a tech guru is I could literally create basically a personal assistant using AI to manage my email, manage my schedule, draft email responses for me, draft text message responses for me, route my days. Like there's infinite possibilities to leverage all of the technology, both that the company is providing and the resources that you want to bring yourself to become as proficient as humanly possible. Because what you're going to see— and I highlight this, by the way, in the 2025 to 2028 roofing market reports— as I look at the future trends, you can get a free copy of that, by the way, in the link in the description or by going to roofmarketreport.com. There's no catch. I would recommend getting in there and reading that. And when you're in there and reading the report, you're going to see that sales per rep is going to keep going up, up, up, up, and up. In fact, there's a member of RSRA whose monthly quota, in other words, the minimum to just keep your job, is $200,000 a month in sales, with their average between $200,000 and $500,000 per month. Why? Because of leveraging technology. These are the types of conversations that we're sharing inside RSRA, how we're doing these things. And what's working and what's not. But as you think through as a salesperson, how do I become as efficient as I can to make the most amount of sales in the shortest period of time so I can handle an even bigger volume? That would be my focus is like, I just want to be a total whiz. Almost like how one of our members in RSRA just ran a session sharing how they're doing direct mail in-house at scale for far cheaper than using agencies and how we're They're building AI agents to handle workflows. These are the types of things I would start thinking through as a salesperson who wants to leverage AI and technology to absolutely crush it. And that brings me to number 5 on the list. But before I hit it, I just want to share, if you haven't heard my story, I fell into this business in 2011 because I was a massage therapist following my passion in natural medicine and trying to get a practice going. I could not make ends meet and I was making under $19,000 a year when my stepdad Ron told me about the roofing industry and I ended up falling into it after looking at Craigslist ads and found out that his like, you can make six figures selling roofs door to door claim was true and it totally changed my life. And I really hope this video helps you do the same. If you want more on that, I recommend reading my book. It's called The Roofing Sales Survival Guide: How to Beat the Odds, Overcome Yourself and Win Big. And it became a number one bestseller. You can get a free copy on or in my free training center or order a copy on Amazon or Audible. Now back to number 5 on this list would be using AI to be very specific in prospecting for the right neighborhoods and homes. The data that's available right now is insane. You can go to agencies or you can do this online. We just built a tool inside RSRA, a D2D retail neighborhood targeter. We can plug in zip codes, and it will tell you which neighborhoods to target. So you can create these and look at public resources to pull history, by the way, of last roof replacements done. So you don't want to go knocking for retail roofs or targeting certain neighborhoods if the roofs were just done in the last 5 years. I would look at neighborhoods where, again, using resources available— I know even Hailtrace has a lot of this information inside, on the average home value, the average income, how much equity they have in their home, when the roof was last replaced. And I would get really specific piggybacking on to number 4 about using technology so I can be really, really focused on where I spend my time and my energy. Because when I got into this in 2011, it was a giant mystery. Even when there were hailstorms, there was a map that was physical that you had to mail order. We didn't have the little blue dot. Following you around in a hail swath, and we just kind of mysteriously went into neighborhoods and did your best efforts after spending hours and hours and hours driving around. But with all this new technology, you can get laser-focused on people that are— have a high likelihood of needing a new roof and knowing whether or not they can afford it. Thanks for joining me in this video. If you want even more free resources to dominate in 2026, go to adamsfreestuff.com and get access to my free training platform.