Your First Salesman Has to Pay for His Own Seat

The problem in one breath

Every estimate in the company still comes out of your truck, so bids go out late and warm homeowners go cold. A salesman looks like the fix. Then it's month three, he's cost you every single week, and the board shows two roofs sold.

Why it happens

A salesman feels like relief, so you hire one before there is anything for him to sell with. No price sheet, so he prices off his gut and gives away your margin one kitchen table at a time. No paperwork standard, so every contract he writes is a different contract. Nowhere for leads to come from, so he "prospects," which mostly means sitting in a truck. And nobody wrote down what he has to sell to be worth the seat, so no month ever settles it. That's not a bad hire. That's paying a stranger to do your job without the tools you do it with.

The play

1. Build the four things that exist before he starts. A price sheet he can't freelance off, built off the job-cost sheet. One contract, same every job (Play 18, "Before Anybody Tears Off"). A place leads actually come from — storm canvass, past customers, referrals, paid ads, something you can name. And the company answer to "can you cover my deductible?" (Play 16), so he doesn't invent one at a kitchen table.

2. Set the number he has to hit, in sold dollars. Price his seat loaded — pay, burden, gas, phone and what his leads cost you — then divide by your gross margin. That's the sold dollars a month he has to write to pay for himself. Divide by your average job size, then by four: roofs a week. A man who knows "three roofs a week" knows the job. "Go sell" is not a number.

3. Fund the ramp before you make the offer. He will cost before he produces — learning your prices, your crews, your market, and waiting on first checks to clear. Decide now how many months you're willing to carry him and put that cash aside. A ramp you never funded turns into a panic firing in month two.

4. Pick the pay structure with your eyes open. Straight salary and you carry all the risk. Commission only and he carries it — but he'll chase whatever pays him fastest, which isn't always the work you want. A draw against commission splits it — and the fight is always whether that draw is recoverable, so get it in writing before day one. How commission-only pay and draws have to be handled, and whether a salesman can be 1099 at all, is a state and federal question — your accountant answers it, nobody at the supply house.

5. Tell him the worst of it, then set a trial with a date on it. Run the hard-truth interview — storm chasing, no-shows, months where nothing closes. Then write the trial into the written offer sheet: the sold dollars, the date you both look at it, both signatures. Make his sold dollars this week's one number for him. You'll know by week six, not month six.

Do this this week

Fill one row of the next-hire sheet for the salesman seat — pay, burden, gas and phone, what his leads cost — and read the "jobs a month" number out loud. Twenty minutes. If you can't picture him selling that many roofs in your market, you just saved a year of paying to find out.

The tool

The next-hire math sheet lives on Play 08, "Can You Afford Another Crew?" — one sheet covers every seat. Give the salesman his own row. Pay (B) is his salary or draw; burden (C) is your payroll percentage, or 0 if he's a true 1099; column D is his gas, phone, sample board and what you spend to put leads in front of him. F is the number that matters — sold dollars a month — and G turns it into roofs. In H, put the weeks between the work getting done and the money landing. Then write the trial down:

SALESMAN TRIAL — the number and the date, in writing

Name: ____________________       Start date: __________

Before day one (all four, or he doesn't start):
   [ ] Price sheet he can't freelance off
   [ ] One contract, same every job
   [ ] Where his leads come from: ______________________
   [ ] The company answer to "can you cover my deductible?"

Pay:  [ ] salary   [ ] commission only   [ ] draw against commission
      Draw amount: __________   Recoverable?  [ ] yes  [ ] no

His break-even:  $__________ sold per month  =  ______ roofs a week

TRIAL:  $__________ sold by __________ (date)
        We sit down that day, both of us, and decide.

Signed: ______________________ / ______________________

If your crew is 1099

Here the 1099 question is about the salesman himself. A true independent contractor works his own hours, his own way, and can sell for somebody else; the more you hand him a set schedule, a script and a territory, the more he looks like an employee no matter what the agreement says. Where that line falls is your accountant's call. Either way, what you can put in a contractor's agreement is the work product: your price sheet is the only pricing he may use, your contract is the only paperwork he may write on, and the trial number and date stand. Terms about the job, not supervision.

One more thing: this play is how we run a shop — it's not legal advice. Rules change by state and by contract, so before you act on the legal-sounding parts, run them past your own attorney or accountant. It's your business, and what you do with any of this is your call and your responsibility.