Starting in Roofing Sales: When to Go "All In" or Get a Part-Time Job?

A YouTube video by Adam Bensman advising new roofing salespeople on whether to commit full-time or keep a part-time job. He shares personal experience of quitting a low-paying job to pursue commission roofing sales, outlines expected ramp-up time (roughly 6–8 weeks to get paid, possibly up to 6 months), and gives practical guidance on assessing risk tolerance, household responsibilities, contingency plans, and optimal scheduling for part-time work (avoid nights/weekends).
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If you're new in roofing sales or considering a career in roofing sales, I'm guessing you're wondering when should you go all in? Should you be doing this on the side of your full time job or do you try to split the difference by doing this most the time and getting a part time gig? And maybe you're wondering how long is it going to take to start getting money rolling in. Well, I'm going to be answering all that and more in this video of sales talk over coffee. First, I want to say a quick welcome or welcome back. Adam Bensman here, the roof strategist. And everything that we do here in my program, in my sales training, in my free training center in our community and mastermind called the Pitch Pro Movement. And when I'm out speaking and training companies is all designed to help you and your team smash your income goal and give every customer an amazing experience. And I just want to say welcome because the fact that you're here tells me that you're excited about betting on yourself, trying something new and investing in a new career path that could absolutely transform your life and help help you earn life changing money. And in fact there are a lot of roofing salespeople that in their very first year hit the six figure mark, hit the multi six figure mark and sometimes earn even $300,000 in their very first year. But getting there is the hard part and getting started is the hardest part. So I want to talk through a few of these different scenarios because everyone is going to have a different view and different comfort level on what kind of tolerance for risk they have. When I got into the business, it was in 2011. I was a massage therapist at a franchise and I was earning under $20,000 a year living on a strict $4.20 a day in groceries. I never went out to eat. Now I was lucky enough that over the years I was squirreling away a little bit of money at a time and I had $2,000 roughly saved up which was about six to eight weeks of Runway cash flow wise for me to make this thing work. And many people had given me the advice to say, Adam, don't leave the stability of the massage therapy gig to go all in on this commission only job. It's door to door. Who does door to door sales? It's commission only. You have no sales experience. It's roofing. You know nothing about roofs. And I get it. Those people truly loved me and they wanted what was best. But I knew in my heart of hearts as I began calculating how our company worked, that I would likely earn more in one roofing sale, just one, than an entire month doing them a massage therapy at that franchise I was working at. So I made this decision. It was a very scary decision. Do I juggle it? Do I not? But I want to share with you how I made this decision and what decision I made. I started to look at my hours at the massage therapy franchise, and I was working nights because that's when people want a massage, and weekends, which is when people want a massage. Now, unfortunately, that is the absolute prime time to be out selling roofs. So for me to try to juggle it meant that I was out trying to knock doors at like 10 o' clock in the morning on the weekdays. And. And the more that I started to try to juggle this, I realized, like, I can't give this my all, and if I try to put one foot on either side, I'm just going to delay or one foot's going to slip, I'm going to fall on that fence right between my legs and it ain't going to feel good. So I made the decision to go all in. I gave my notice, I quit the massage therapy gig, and I gave roofing sales all I had. Now I'm the type of person, I visualize what's going to happen, and I did not doubt myself. Now, was I scared and did I get nervous at times? Absolutely. But when I made that leap in my mind, I was already successful. I had already hit that income goal and I knew I could. I bet everything on myself. And I built the metaphorical parachute on the way down after jumping out of the plane. But at that time, I was in my 20s, I was living alone, I was not married, no children, and little responsibility. So I could make that leap. And I would encourage you as soon as you're able, because I'll touch on this in a second. As soon as you're able to go all in. But I have spoken with folks who are a father, they're the sole incomer of the household, and they have four children. I would be probably jeopardizing the livelihood of an entire family if I was like, you got this man, because I don't know you, I don't know your situation. I didn't know if you have other financial obligations and everyone's risk tolerance is different. But objectively speaking, the sooner that you can go all in, the better, because the time and energy to get things going and roofing sales will generally take. And people are different. But there's about a Six to eight week delay from sale to getting paid. Now every company is different. Some companies these days are offering a low base pay or a salary or advances on commission or draws that can come in early or startup pay. There's a whole variety of pay plans out there and if you want to learn more, you can watch my videos on pay plans and roofing sales. We'll link to that card up here. And what I think is fair, just the common pay plan so you can kind of shake that out for yourself to see what that looks like. But generally speaking, count on six to eight weeks if you're successful out of the gate. And you may want to buffer for two to three months of light cash flow as you get going. There's a gentleman who emailed me by the way, he had earned, I believe I'm going through my memory, I believe it was a little over 200,000 in his first year probably. But getting started was slow. He had I think a few hundred dollars of commission in the first month, I think like 2000 in the next month, maybe it was 3 or 4000 thereafter. And then it shot up to 20 and it kept pace in those big numbers every single month. But that little trickle was like I started to get a little taste, started to do okay, oh, now I'm figuring out doing a little better. And for many people they end up quitting too soon. And this gentleman, if he would have quit in those first three months cause he wasn't seeing the big money coming in, would have missed out on earning multi six figures and in his first year. So I just want you to be prepared with realistic expectations that the absolute hardest part of this industry is your first six months, getting into it, getting started, getting in the swing of things, feeling confident, learning a new craft, learning new sales, being in new environments and challenging yourself. So first question, do you go all in as soon as you can? Yes. Second question, how long is it going to take? Six to eight weeks, maybe as long as six months. Depends on the market, depends on when you start. And if you're starting, let's say selling in Iowa and you get hired in February, it's cold, you might not be that active until the spring. So again there is some considerations in the seasonality that you'll want to keep in mind. I would highly recommend that you speak with the company that you're selling for or considering selling for to ask them what they would expect the ramp up time to be based on their comp plans. Now the last thing that I want to address in this video Is the idea of this part time job thing, do you do it or do you not do it? I've worked with quite a few roofing salespeople who've had jobs specifically bartending, because that's how they came into it. They're good with people, they can handle conflict, they're used to people being rude, and they channel those skills in a way in sales to earn really good money. But that cash flow, there's that delay as we get started. So these folks decide to keep their bartending job as they get traction more often than not. What I've found is they reach a point where they're like, well, why would I do that? I'm making more on sales now. I can make that pivot and. And then they go all in. So very few people will keep that in the long run. But there's one big, big, big problem with the bartending side jobs. They have a tendency to demand weekend hours or evening hours. And again, it depends on where you're at. But my best advice is that if you get a part time job, you find someplace that will allow you to work in the mornings during the week. This will free up your time to be free in the evenings and the weekends, which is the single most valuable time. I guess it's not single if it's seven days a week. My point is the nights and the weekends are the most valuable time for you to be out knocking doors, making sales, or running appointments for your company, because that's when people are home. And if you can do that, you'll have the best availability to start making sales. So you can go all in even quicker and ditch the part time job. Now, the key takeaway is you need to assess your own threshold of one, your risk tolerance, two, who's depending on you and three, do you have a contingency plan? I always hope for the best and plan for the worst. And I was fortunate enough in my 20s to know that if I burned through my money and I went two months without making any sales, I could jump back into a massage therapy franchise and pick up another one to continually earn not great money. While I tried to make this work, I also knew that my brother lived just around the corner and I'd probably be able to crash on his couch if I needed to. And I know that I've got two loving parents that wouldn't, you know, if push came to shove, I'd have a couch to crash on, hot meals, and some love and support as I bawled my eyes out, feeling like a failure. But at the end of the day, I just want to commend you because the fact is you're looking at a new career or starting a new career, you're taking a risk and that's admirable. And whether or not it even works out, you deserve a pat on the back. And I mean that from the bottom of my heart. Because you're betting on yourself. You're trying something new, you're challenging yourself, you're putting yourself into an uncomfortable position. And if you play your cards right, which I'm guessing you are, because you're here doing your homework and learning about this industry, you too have the capabilities, the full capabilities to apply yourself, gamify this personal development, change your life and earn six figures or more in your very first year. So I'm really honored to have you here and to help support your journey to so congratulations again and remember, go all in as soon as you can juggle that risk. Get a few months saved up so you're in a comfortable position to make that transition. And I hope that you are absolutely wildly successful in roofing sales. Thanks for joining me on this video. And just cause our time here is about to wrap up doesn't mean your and my time has to I'd like to invite you to join me inside the free training center. You can click here to get in there and inside click on the pitch like a pro. Roofing Sales training video library there's three playlists right at the top that are perfect for the beginner or soon to be beginner roofing salesperson. And if you want to hang with me here on YouTube, hop into this video and I will see you on the next one.










