Owner-Operator Roundtable
Checklist8 min readFocus · August

Compliance for Year One Employers

I-9, W-4, state registrations, and the paperwork everyone forgets.

Focus for August

Q3 payroll-tax checkpoint

August: catch any year-to-date wage or tax mismatch while it's still small.

Refreshes on the 1st of every month

Reconcile YTD wages, federal/state withholding, FICA, and unemployment. A small variance in August becomes a W-2 nightmare in January.

  • Reconcile YTD wages to GL
  • Verify FICA caps applied correctly per employee
  • Confirm SUI rate matches the state notice
  • Resolve any payroll-provider tax notices
01

Federal setup

  • Apply for EIN (irs.gov, free, 10 minutes)
  • Set up federal tax deposit schedule (EFTPS enrollment)
  • I-9 for every employee within 3 business days of start date
  • Store I-9s separately from personnel files (not in the HR folder)
  • Collect W-4 before first paycheck
  • Report new hires to federal/state new-hire registry within 20 days
  • Set up workers' comp coverage before day one (most states)
02

State setup

Order matters — getting these in the wrong sequence triggers late-filing penalties.

  1. Register for state withholding tax
  2. Register for state unemployment insurance (SUI) — get your rate
  3. Register for state new-hire reporting
  4. Workers' comp policy bound and certificate on file
  5. If you have remote employees in other states, repeat 1-4 for each state
03

Posters, handbooks, and policies

ItemRequired?When
Federal labor law posterYesDay 1
State labor law posterYesDay 1
Written sexual harassment policyMost states ≥1 employeeDay 1
Employee handbookNot required, strongly recommendedBy hire #5
PTO/sick leave policy in writingRequired in most statesBefore first PTO request
At-will acknowledgmentRecommendedHire date signature