Compliance Contractor

About The Role

We are looking for a detail-oriented compliance contractor to help rebuild our state and local compliance system over a 12-week project. The work covers an account register, state requirements research, a certificate and renewal tracker, and a 12-month compliance calendar with a runbook to go with it. You'll research and recommend, and we'll make the decisions and handle filings and payments. This is a project-based engagement with clear deliverables and a defined end date.

What You'll Do

• Build a register of every state and local registration, tax account, and insurance carrier, with owners and renewal dates. Record account numbers only as masked references.
• Research and document state requirements for each state where we have employees or other nexus: unemployment filings, withholding, new-hire reporting, required postings, paid leave, workers' comp, and local taxes. Cite a primary source and a verification date for each item, and list anything you couldn't verify as an open item.
• Build a certificate and renewal database for insurance, licenses, permits, and registrations. Collect and check vendor certificates, and flag anything 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 run without you.
• Deliver an evaluation memo recommending whether we should continue this work, hand it off internally, or outsource it after the term.

What Success Looks Like

• All six deliverables will be delivered by the end of the 12-week term, owned by the contractor.
• Compliance calendar will have an owner and an approver for every item by the end of the term, owned by the contractor.
• State requirements will cite a primary source and verification date for every item, with any unverified items listed as open, owned by the contractor.
• Certificates and licenses will each have an expiration date and document link, with nothing expiring within 90 days left unflagged, owned by the contractor.
• Handoff will be confirmed before the term ends: the People Ops Manager updates one calendar item and one certificate renewal using only the runbook and records, without asking the contractor for help. Owned by the contractor, confirmed by the People Ops Manager.

Must Haves

• Working knowledge of state unemployment, payroll tax, and workers' comp requirements, with experience across more than one state.
• Experience building compliance calendars, trackers, or checklists in a spreadsheet.
• Able to work without daily direction and to 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.

Core Values

• Be the person people can count on: You own the compliance calendar end to end and set clear expectations for every deadline.
• Clear focus: You prioritize the filings and deadlines that matter most and communicate status in plain terms.
• Grit and growth mindset: You take on the hard research questions, verify what you find, and improve the system as you learn.
• T.E.A.M. (Together everyone achieves more): You leave a runbook and calendar the whole team can use, so the work doesn't stop when the project ends.

Why This Role Matters

Accurate compliance records protect us from missed filings, lapsed insurance, and avoidable penalties. Right now our account information, certificates, and deadlines are spread across several places. A clear calendar and a reliable certificate tracker mean nothing slips through, and our team can run the process with confidence after the project ends.

Terms of Engagement

• Compensation: $1,000 – $2,000 per month, depending on the final agreed scope of work and jurisdictional coverage.
• Hours: Up to 40 hours per month. No minimum hours are guaranteed, and you set your own schedule.
• Work: You control your methods, location, and schedule, and you may serve other clients. There are no fixed daily or weekly meetings. We check in when each deliverable is delivered.
• Equipment and tools: You use your own equipment and business tools.
• Access and security: Access is only through a company-controlled password manager, limited to what the deliverables need, and removed at the end of the term.