The January Playbook for a Roofing Company Owner

January is the month that decides your year

If you treat January as recovery from Q4, you burn six weeks of runway and walk into the spring ramp unprepared. The owners who hit 20 percent year over year growth in year five and beyond run a tight January playbook. They close the prior year, file the paperwork, roll out the new comp plan, renew licenses, and refresh the pipeline before the first warm week in March.

This is the owner checklist we use and the same one we ship inside RoofKnockers as a January kickoff template.

Week 1: Close the prior year financially

Your CPA needs clean books by January 15. If you hand them a mess, they bill hourly and your return slips to April. Give them a clean handoff and you keep planning time.

• Reconcile every bank and credit card account through December 31
• Match every supplier invoice to a job and close open POs
• Post year-end journal entries for inventory, deprecation, and owner draws
• Run a P&L by month and a balance sheet snapshot as of 12/31
• Pull a job costing report for every job closed in the prior year

Budget for this: 20 to 30 hours of bookkeeper time plus 4 to 6 hours of your time. If you are still on QuickBooks Desktop and pasting spreadsheets, the hours double.

Week 2: W-2s, 1099s, and tax paperwork

The IRS deadline for W-2s and 1099-NEC is January 31. Miss it and you owe 60 dollars per form up to 630,500 in penalties for a small business. Do not miss it.

W-2 checklist

1. Confirm every employee address, SSN, and filing status in payroll
2. Review box 14 items: uniform deductions, personal use of company vehicle, PTO payout
3. Run a preview W-2 for each employee and have them verify before January 20
4. File electronically with the SSA and distribute employee copies by January 31

1099-NEC checklist

Every subcontractor you paid 600 dollars or more to in the prior calendar year needs a 1099-NEC. Collect W-9s now for any you are missing. Our rule: no W-9, no payment in January. That gets them on file fast.

Week 3: Comp plan rollout and licensing

Roll the new compensation plan before sales reps see February leads. Reps need to know exactly what they get paid on what margin, what draws look like, and what the new bonus ladder is. Print it. Have them sign it. File it.

Our recommended structure for canvassers, closers, and project managers:

RoleBase or DrawCommissionBonus TriggerCanvasser15 per hour minimum100 per signed inspection500 at 20 signed per monthCloser2000 monthly draw7 to 10 percent of job gross1 percent of net on 75,000+ monthsProject managerSalary 55,000 to 70,0001 percent of job grossQuarterly quality bonus tied to zero callbacks

For licensing: every state is different, but roofing licenses, contractor bonds, and insurance COIs usually renew on the calendar year. Build a recurring task in RoofKnockers for each license 45 days before expiration. Miss a renewal and you cannot pull permits. That kills jobs.

Week 4: Pipeline refresh and planning

By January 25, your CRM should be clean. Here is what clean means:

• Every lead older than 90 days marked as lost or nurture with a reason code
• Every open claim with a next step and a date
• Every scheduled install for January, February, and March visible on one calendar
• Every rep pipeline below 250,000 flagged for a Monday conversation

Run your annual kickoff meeting the last Friday of January. Read our guide on how to run a roofing company annual kickoff meeting for the full agenda.

The January owner scorecard

By January 31, you should be able to answer yes to every one of these questions:

1. Are the books closed through 12/31 and handed to the CPA?
2. Are W-2s and 1099s filed and distributed?
3. Is the new comp plan rolled out, printed, and signed by every rep?
4. Are all state and local licenses renewed through the next cycle?
5. Is the CRM cleaned and the Q1 pipeline visible in one dashboard?
6. Did the team hear the annual goals, the territory plan, and the comp plan in one kickoff meeting?

Six yeses is the bar. Five yeses and you are behind before March. For a full quarter view, read our quarterly business review guide.

What the best owners do differently

The owners who scale past 5 million in revenue use January to raise the margin floor, not just close the books. They review the prior year job costing reports and find the bottom 20 percent of jobs by margin. They ask: what did we underprice, what took too long, and what supplement did we miss? Then they bake those answers into the new price book before the first February estimate goes out.

FAQ

Should I give out bonuses in January or December?

December if you want the write-off in the prior tax year. January if you want to tie the bonus to the annual kickoff and use it as a motivator for the year ahead. Most owners we work with split: 70 percent in December for tax reasons and 30 percent as a January kickoff bonus tied to showing up and signing the new comp plan.

How long should the January planning meetings take?

Budget 12 to 16 hours of owner time total for January planning. Four hours for financial close review with the bookkeeper. Four hours on the comp plan. Two hours on license and compliance. Two to six hours on the annual kickoff prep.

What if my prior year books are a mess?Pay a catch-up bookkeeper. It is 3,000 to 8,000 dollars depending on the mess and it is worth every dollar. You cannot plan a year on bad data. Hire it out, get clean, and build the discipline to close monthly going forward.