The Complete Roofing Sales Playbook: Logan Schepper's Journey from High School to Senior PM
· Updated · Yash Singh
Logan Shepard graduated high school in 2024, spent a summer selling car wash memberships, and got recruited into roofing by customers washing their company trucks. One year later, he is a senior project manager at a roofing company in Austin, Texas. In this episode of TradeOps Radio, he covers the commission split structure, the door knocking mindset that gets you through the early grind, and the full insurance claim process from first knock to final check.
Introduction
Logan Shepard was netting $50 to $100 a week after bills at a car wash when roofing company drivers started asking if he had ever considered door-to-door sales. He looked at roofing, solar, and pest control. He chose roofing, interviewed a few companies, evaluated the commission split and growth trajectory, and picked one. One year later: senior project manager with guys under him to train.
In this episode, he walks through how the commission structure actually works, what it takes to get past the mental block of asking someone for $30,000, and the complete process from knocking the door to collecting the final check.
The Pay Structure, the Mental Shift, and the Door Knocking Foundation
How the commission split works. Industry standard is 30 to 40% of the project profit, not the total insurance check. If insurance pays $30,000 and the job costs $23,000 to complete (labor, materials, everything), the $7,000 in profit is what the split applies to. At a 50/50 split (which is above standard), that is $3,500 to the rep. Logan’s company started him at 50/50, which is one of the criteria he evaluated when picking where to work. Alongside that: the PM role handles A to Z with no middleman, a 1099 structure that gives schedule flexibility, and owners who push without micromanaging.
Getting comfortable asking for $30,000. Going from car wash memberships to five-figure roofs is a genuine mental shift. Logan’s answer is product knowledge. When a homeowner asks “why does it cost so much?” for a $16,000 retail roof, the response is a breakdown: shingles, labor, underlayment, pipe boots, decking if needed, warranty. “You’ve got to go into detail to make it sound like it’s worth it. And it is worth it. When you’re using the right materials and the right crews, this is one of the biggest investments you’ll make on your home.” The pitch is not price defense. It is a reframe from expense to investment.
For fence-sitters without urgent damage, the angle is proactive pain: “You don’t want to wait until a leak happens and then replace your drywall and repaint your ceiling. Do the roof now. I’ve had homeowners decide to wait and call me months later saying, ‘I wish I’d listened to you. Now I have $3,000 to $4,000 in ceiling repairs on top of the roof.'”
Door knocking: the honest take. “Door knocking sucks. You have to lie to yourself and tell yourself these people have been waiting for me to come to their door.” Some of them genuinely have. Logan has knocked on doors where homeowners thanked him for showing up. He has also knocked on doors where someone answered with a hand on a holstered gun.
The value of door knocking is not just leads. It is product knowledge built from real customer questions you never anticipated. Logan fumbled a question about how long the company had been in business and lost the deal. He thought about it, built a better answer, and never fumbled it again. “I need to figure out how we haven’t been in business long” became: “We’ve been in business almost two years. Two of my three owners came from roofing and have been in it for almost a decade each. They realized they could do it themselves, took the risk, and it’s been flourishing ever since.” That one story from a lost deal is now one of the best things he says on a door.
Door-to-door compliance basics. No soliciting sign: low risk to knock, but Logan skips them except on the first day after a storm when homeowners are actively searching. No trespassing: do not knock, ever. Some neighborhoods require a solicitor’s permit. Without one, leave immediately if asked.
The pitch approach. First 10 to 15 seconds: nothing about the roof. Sports team flag, military decal, anything relatable. “I’m a sports guy. Any team you have up there, I’ll find one fact I can relate to.” Once the guard drops: “Hey, I don’t want to take up too much of your time. Reason I’m here is your neighbor Chris next door I was up on his roof, noticed some hail damage, he told me to swing by yours while I was here. It’s complimentary. No obligation. Just trying to earn some business out here and help my neighbors.” Specific neighbor, not “the neighbor down the road.” Real name, real relationship.
Long-term, door knocking gives way to networking. Logan now spends most of his time meeting realtors and insurance agents in Austin, Pflugerville, and Georgetown. Cross-referral from HVAC techs, plumbers, and landscapers who see damaged roofs while on jobs is the goal. “Eventually, I might never have to knock a door again.” That transition starts with compounding relationship volume.
The Insurance Claim Process, A to Z
The insurance side of roofing is where most of the big tickets live, and the timeline surprises most new reps.
Getting the claim started. After the inspection, Logan takes photos of everything and puts together a detailed inspection report, with each photo captioned to explain what the homeowner is looking at. If there is enough hail damage, he recommends filing a claim and will help the homeowner file it on the spot. The call takes 10 to 15 minutes. Most homeowners have never filed a claim before and appreciate having someone walk them through it.
Working the adjuster. When the insurance adjuster schedules their visit, Logan asks to be there. “At the end of the day, he works for the insurance. He’s not like me.” He walks alongside, lets the adjuster do their job, and raises any damage that gets missed fencing, satellite mounts, anything visible. If he disagrees on something, it is a civil conversation. Sometimes it changes the scope. Sometimes it does not.
Depreciation and the final check. After approval, insurance pays 50 to 60% upfront and withholds the rest as depreciation. This was introduced with the Texas deductible law in 2019 to prevent homeowners from cashing out without doing the work. After install, Logan submits completion photos to insurance to release the depreciation. That takes another one to two weeks. Then he collects the final check from the homeowner. Total from first knock to final check: a month to a month and a half.
What new reps need to know. The pipeline lag is real. Get leads in April, get paid in May. For the first two months, there is no income from work you are doing right now. “I tell my guys: you’re going to have to grind. You will always have something rolling in as long as you’re going out every day and getting leads. But take two or three weeks off, and the next month your pipeline is empty.”
Cash deals move faster: 50% before the job, 50% day of install, paid out the next day. Those come later, usually after you have insurance jobs built up and start meeting homeowners who need basic repairs or replacements without an insurance claim.
FAQ
How does commission work in roofing sales?
Commission is calculated on profit, not the gross insurance payout. If insurance pays $30,000 and the job costs $23,000 to complete, the $7,000 profit is what the split applies to. Industry standard is 30 to 40% to the rep. More experienced reps or early hires at competitive companies can negotiate higher splits.
How long does the full insurance roofing process take?
About a month to a month and a half from filing the claim to collecting the final check. Insurance pays 50 to 60% upfront after approval and withholds depreciation until the roof is completed and documented. New reps should expect their first paycheck to come in month two, not month one.
What is the best approach to door knocking for roofing leads?
Talk about anything but the roof in the first 15 seconds. Use a specific nearby neighbor as your reason for being there, not a vague reference. Keep the tone casual, not scripted. Expect rejection and use every awkward moment as a diagnostic if you could not answer a question the homeowner asked, go learn it before the next door.
When should roofing reps transition from door knocking to networking?
Door knocking is the best starting point for building product knowledge and pitch confidence, but it is not a long-term primary channel. As storm season cools off and referral relationships build, networking with realtors, insurance agents, and other home service trades (HVAC, plumbing, landscaping) produces warmer, easier-to-close leads.
What compliance rules apply to door knocking?
No soliciting signs carry low formal enforcement risk but indicate homeowners who do not want to be approached. No trespassing signs are a hard stop. Some neighborhoods and counties require a solicitor's permit to knock. Without one, leave without knocking if asked. Being in violation of a trespassing sign while soliciting creates real legal exposure.
Related: Lead generation for HVAC companies.
