Compliance Contractor

Column Software

4d•$1,000 - $2,000

About The Position

This is a project-based compliance engagement lasting 12 weeks, with clear deliverables and a defined end date. The contractor will help rebuild the company’s state and local compliance system, researching and recommending requirements while the company makes decisions and handles filings and payments. The work includes an account register, state requirements research, a certificate and renewal tracker, a 12-month compliance calendar, runbooks for recurring obligations, and an evaluation memo recommending whether to continue the work, transfer it internally, or outsource it after the engagement. The contractor owns the deliverables and is expected to leave a system the team can operate after the project ends. The handoff is confirmed when the People Ops Manager updates a calendar item and a certificate renewal using only the runbook and records, without contractor assistance. The contractor controls their methods, location, and schedule, may serve other clients, and uses their own equipment and business tools. There are no fixed daily or weekly meetings; check-ins occur when deliverables are submitted. Compensation is $1,000–$2,000 per month, depending on the agreed scope and jurisdictional coverage. Work is capped at 40 hours per month, with no minimum hours guaranteed.

Requirements

Working knowledge of state unemployment, payroll tax, and workers’ compensation requirements, with experience across more than one state.
Experience building compliance calendars, trackers, or checklists in a spreadsheet.
Ability to work without daily direction and meet agreed due dates.

Nice To Haves

SHRM-CP, PHR, or equivalent certification.
Experience with insurance certificate tracking or vendor compliance programs.
Experience with state audit or claims processes.

Responsibilities

Build a register of state and local registrations, tax accounts, and insurance carriers, including owners and renewal dates; record account numbers only as masked references.
Research and document state requirements for jurisdictions where the company has employees or other nexus, including unemployment filings, withholding, new-hire reporting, required postings, paid leave, workers’ compensation, and local taxes.
Cite a primary source and verification date for each researched requirement, and list unverified items as open items.
Build a certificate and renewal database for insurance, licenses, permits, and registrations.
Collect and check vendor certificates, and flag items expiring within 90 days.
Build a 12-month compliance calendar with due dates, reminders at 30, 14, and 7 days, and an owner and approver for every item.
Write a short runbook for each recurring obligation so the calendar can be maintained without the contractor.
Deliver an evaluation memo recommending whether the work should continue, be handed off internally, or be outsourced after the engagement.
Complete a handoff before the term ends, enabling the People Ops Manager to update one calendar item and one certificate renewal using only the runbook and records.
Set clear expectations for deadlines, prioritize important filings and deadlines, communicate status plainly, verify research, and leave a calendar and runbook the team can use.