The Business Club.
← Owner-Operator Roundtable
Checklist8 min readFocus · October

Compliance for Year One Employers

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

Focus for October

Year-end W-2 / 1099 prep

October: the cleanest year-end is one that starts in October.

Refreshes on the 1st of every month

Address corrections, missing TINs, and address changes now. January W-2 reissues are expensive and signal sloppiness to every employee who notices.

  • Send TIN/address verification to all W-2 employees
  • Collect updated W-9s from active 1099s
  • Confirm payroll provider's W-2 timeline
  • Resolve any IRS or state notices outstanding
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
More for Owner-Operator Roundtable

Keep reading.

Playbook

13-Week Cash Flow Forecast

A working model and the weekly ritual that keeps it honest.

Read →
Guide

Your First Five Hires

Org-design templates from operators who've done it twice.

Read →
Template

Owner-Comp Framework

Salary, distributions, and reasonable comp without the guesswork.

Read →