Owner-Operator Roundtable
Checklist8 min readFocus · June

Compliance for Year One Employers

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

Focus for June

Mid-year handbook check

June: laws moved this spring. Your handbook probably didn't.

Refreshes on the 1st of every month

Pay-transparency, paid-leave, and AI-in-hiring rules are changing in many states each year. A 30-minute update now beats a quiet violation that compounds for six months.

  • Subscribe to a state-law update from your PEO/HR partner
  • Review pay-transparency requirements where you operate
  • Confirm leave policies match current state law
  • Re-acknowledge the handbook if material changes
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