Hire first for the work that keeps you from selling and running jobs. If that work is phones and paperwork, your first hire is office help, and if your salespeople are stuck writing estimates, it’s an estimator. A production manager comes in once you can’t check every roof yourself, and a sales manager once you have more reps than you can coach.
No public data shows which role roofing companies hire first, so move a role up the list if it’s the one holding you back. Growing a Roofing Company Past the Owner: Systems, Hires and New Services covers the rest of building a company that runs without you.
Office help comes first when phones and paperwork take your selling time
Roofing contractors employ more office staff than salespeople. In May 2025, office and administrative support made up 9.95% of their wage and salary workers, and sales made up 5.41%.
BLS has no line for a roofing office manager. The closest national medians at roofing contractors in May 2025 were $45,790 for an office clerk and $55,300 for a bookkeeping clerk, before benefits.
Offshore help costs less. A Denver roofing owner on r/Entrepreneur was weighing virtual assistants in the Philippines at $6 to $8 an hour to take routine tasks off staff paid $20 to $40 an hour during the off-season.
Before you post the job, write down a week of tasks you did that didn’t need you on a roof or at a kitchen table, and hire for that list.
Hire an estimator when your salespeople are stuck writing estimates
An owner on r/RoofingSales asked how common a full-time estimator is, because “our salesman are also responsible for drafting estimates/contracts which has turned into a bottleneck.” He was weighing a dedicated estimator against an outsourced virtual assistant. If your reps write up their own estimates and contracts, an estimator gives that time back to selling.
Cost estimators at roofing contractors earned a national median of $77,480 in May 2025. Weigh that salary against the jobs your reps could sign with the hours they get back.
You can also send the writing out. An owner on r/Roofing opened a thread on using freelance Xactimate estimators for insurance estimates in place of an in-house hire. If estimates pile up only after storms, try a freelancer before you hire; if they pile up every week, hire.
If your estimator will write Xactimate estimates and supplements, Verisk certifies users at three levels (fundamentals, proficiency and mastery), and each level is required before the next. Every exam includes a hands-on lab where the candidate builds an estimate from a sketch and a scope, and certification is valid for two years. Ask candidates for their level and the date they passed. Xactimate for Roofers: Which Line Items Matter and Whether You Need It covers the software itself.
In Texas, the Insurance Code bars a roofer from acting as a public adjuster on any property where it does or may do the work. That rules out offering to negotiate the claim settlement or filing the claim for the homeowner. TDI says the same chapter still lets a contractor provide estimates and discuss them with the insurer’s adjuster. Write that line into the estimator’s job description, and check your own state’s rules if you work outside Texas.
Some estimators qualify on experience alone, so look inside your company first
Job boards came up short for one large commercial roofing company. Someone hiring several estimators there wrote on r/Construction that “Indeed and Linkedin are not cutting it right now,” and asked where estimators gather and which related jobs carry over into commercial roof estimating.
BLS lists a bachelor’s degree plus on-the-job training as the typical entry route, and says some construction cost estimators “become qualified solely through extensive work experience.” That puts a salesperson who already measures roofs, or a crew lead who knows materials, in the running. Train them on your estimating software and check their first estimates against final job costs.
For commercial work, ASPE’s Certified Professional Estimator credential takes at least five years of verified estimating experience, several exams and a technical paper. That makes it the mark of a seasoned hire, so leave it out of the requirements for a first estimator.
If you’re the roofer or rep who wants to become an estimator, the same path applies. Learn on estimates someone checks against job costs, then add Xactimate certification for insurance work, or the CPE once you have five years of estimating behind you.
A production manager takes over when you can’t check every roof yourself
BLS has no line for a roofing production manager either. At roofing contractors in May 2025, first-line construction supervisors earned a national median of $71,500 and construction managers $96,540.
A Tennessee owner about a year and a half in posted on r/smallbusiness that his company was on track for $3 million to $4 million with six salespeople and project managers, and that he was training his project managers and documenting standard procedures. Write your own checklist for a job, from material drop to final walk, before a production manager starts, so they have your standard to run.
A sales manager needs a sales team, and a general manager comes last
BLS has no line for roofing sales managers. The nearest figure is the $71,310 national median for sales reps at roofing contractors in May 2025, commissions included. A sales manager hires and coaches reps, so the role pays once you have more reps than you can coach yourself. If one of your reps already trains the new ones, start there. How to Hire and Train Roofing Sales Reps Who Find Their Own Leads covers hiring the team they would run.
General and operations managers at roofing contractors earned a national median of $102,330 in May 2025. A general manager runs the roles below them, so fill those first and hire the GM to run people and procedures you already have.
An office manager on your hours and software is hard to call a 1099
The IRS sorts contractors from employees by behavioral control, financial control and the type of relationship. An office manager who works set hours in your office on your software is hard to defend as a contractor under that test. The Tennessee owner said his project managers and admin are 1099, which carries the same risk.
Overtime has its own test. Federal law exempts outside salespeople from minimum wage and overtime when their main duty is selling and they regularly work away from your office, and that exemption has no salary requirement. An office manager, estimator, appointment setter or in-office sales manager doesn’t fit it. Before you set their pay, ask your accountant which exemption, if any, covers each office role.
The IRS says each new employee needs a completed Form I-9, a signed W-4 and a Social Security number for the W-2. In Texas, an employer without workers’ compensation has to report that to the state.
The SBA says to report each new hire to your state directory within 20 days, and some states set a shorter deadline. You have 3 business days from the hire date to finish the employer’s part of the I-9, so have the forms ready on day one.
Check these before the first hire starts
- List a week of tasks that didn’t need you, and hire for that list.
- Move the estimator up if your reps write their own estimates and contracts.
- Ask estimator candidates for their Xactimate level and the date they passed.
- Write your job checklist before a production manager starts.
- Put office staff and estimators on payroll, and ask your accountant about their overtime status.
- Complete Section 2 of the I-9 within 3 business days and file the state new-hire report.
A salaried hire costs the same in a slow month as a busy one, so it pays to know whether homeowners searching near you can find your company. Run the free Google Maps heatmap: pick your Google profile and a search, and in a few minutes you’ll see your rank at 49 points around your office.