November and December Off-Season Priorities for Roofing Owners

Off-season is not vacation

The owners who show up in November and December build the foundation for a 30 percent growth year. The owners who check out and travel for 8 weeks scramble through January and never catch up.

Here are the off-season priorities we run every year.

Wrap ups

Every job installed in the season should have a final walkthrough and a clean close. By November 15, verify:

• Every install has a completed punchlist signed by the homeowner
• Every warranty package delivered
• Every job photo archived in the CRM
• Every supplier invoice matched to the job
• Every lien released if required by state

Open jobs without clean closes bite you in March when the homeowner calls about a leak and you cannot find the warranty paperwork.

Collections full court press

November and December are the months to collect. Homeowners have year-end money from bonuses, tax refund prep, and gift money. Insurance companies want to close books before year end.

• Call every balance over 30 days weekly
• Send past-due letters at 45, 60, and 90 days
• File small claims or lien at 120 days
• Offer a 2 to 3 percent pay-now discount on balances over 5,000 dollars

Set a company target: AR at year end should be under 15 percent of annual revenue. If you did 3 million, your AR on December 31 should be under 450,000 dollars.

Year-end tax moves

Talk to your CPA by November 15. Review:

Section 179 and bonus depreciation

Every truck, trailer, computer, and tool you bought this year qualifies for Section 179. Up to 1.16 million deductible in 2027. Time big equipment purchases before December 31 if you need the write-off.

Retirement contributions

Solo 401k or SEP-IRA contributions can be made until tax filing deadline, but decide the amount in December. A 5 to 10 percent of net income contribution saves 20,000 to 50,000 on a 3 million company in taxes.

Health insurance structure

If you are running a PC or S-Corp, health insurance premiums structured correctly save another 4,000 to 8,000 in FICA. Ask the CPA to walk through your structure.

Year-end bonuses

Pay bonuses in December for the tax deduction in the current year. Communicate the formula in November so the team is motivated through the last installs.

Team recognition

Run a year-end recognition event in mid-December. Not a drunk Christmas party: a real recognition event. Budget 3,000 to 8,000 dollars for a 3 million dollar company:

• Dinner for the team and significant others
• Awards: top canvasser, top closer, rookie of the year, MVP
• Prize: cash, trip, or something personalized
• Owner speech: 10 minutes on what we did this year and where we are going

Recognition retains talent. A rep who gets a trophy and a 1,000 dollar check in front of their spouse is 3x more likely to be on the team next March.

1099 review

Start 1099 prep in November. Every sub you paid 600 or more needs a W-9 and address:

1. Pull all payments over 600 dollars by subcontractor from the year
2. Verify W-9 on file for every one
3. Request updated W-9s for any missing or expired
4. Build the 1099-NEC run in payroll software by December 20
5. File electronically and deliver by January 31

Missing 1099s cost 60 to 330 dollars per form in penalties. More importantly, subs who do not receive 1099s cannot reconcile their taxes and may refuse to work with you next year.

Strategic planning

Block 3 days in December for strategic planning. No employees, no calls, no email. Three questions:

1. What did we do well this year? (top 5)
2. What did we do badly this year? (top 5)
3. What will we do differently next year? (top 5)

Write the answers. Build a 1-page plan for next year. Share it in January at the annual kickoff. Read our kickoff meeting guide and our year over year planning guide.

Pipeline seeding

Do not let pipeline die over December. Keep light-touch outreach alive:

• Email sequence to last year's retail leads: "2028 is coming, want your free inspection?"
• Referral request to every installed customer from the year
• Social media posts 2x per week with installed job photos

Budget: 500 to 1,500 per month through the off season. You will harvest this pipeline in March.

Off-season scorecard

By December 31:

1. All jobs closed and warranty delivered? Yes
2. AR under 15 percent of annual revenue? Yes
3. Tax moves completed with CPA? Yes
4. Team recognition event completed? Yes
5. 1099s prepped and ready for January filing? Yes
6. Strategic plan written and ready for kickoff? Yes

FAQ

Should I pay myself a bonus in December?

Ask your CPA. For S-Corp owners, the structure matters: W-2 salary plus distribution beats a giant bonus for FICA purposes. For sole proprietors or LLC owners, the distinction does not matter as much.

How much should I spend on year-end recognition?

1 to 2 percent of annual profit. A 3 million revenue company with 15 percent profit margins (450,000) should spend 4,500 to 9,000 on year-end recognition including bonuses tied to performance.

Can I take December off?

No. You can take 1 to 2 weeks between Christmas and New Year if everything above is handled by December 20. Otherwise, stay engaged. Absentee owners create January chaos.