Contract Bookkeeper / HR Administrator

We are two related, established commercial printing businesses in the Chicago area looking for an experienced independent bookkeeper to replace a long-term contractor who is retiring.

This is an ongoing 1099 contractor engagement averaging approximately 20-40 hours per month. The work is primarily remote, and we prefer someone in the Chicago area who can be available in person occasionally if needed.

Our internal staff handles day-to-day accounts receivable and accounts payable activity. We are looking for an experienced professional to handle recurring bookkeeping, payroll administration, month-end work, and basic HR administration.

Typical responsibilities include:

• Bank and credit-card reconciliations
• Month-end bookkeeping and account review
• Payroll administration for approximately 9 employees
• Maintaining accurate general ledger records in Xero
• Routine financial reporting
• Sales-tax and other recurring filings
• Monthly commission calculation, typically involving only 2–5 orders
• Coordination with our independent CPA
• Employee onboarding and offboarding administration
• Maintaining payroll and basic employee records
• Routine HR administration and compliance support
• Maintaining organized bookkeeping procedures and records

Our CPA will remain responsible for tax returns, tax planning, and higher-level accounting matters.

We are looking for someone with:

• At least 5 years of bookkeeping or small-business accounting experience
• Strong hands-on Xero experience
• Payroll administration experience
• Experience with bank and credit-card reconciliations and month-end close
• Experience with basic HR administration
• Strong attention to detail and follow-through
• Experience working independently with small-business owners and outside CPAs
• Experience supporting multiple related companies is a plus
• Illinois payroll and sales-tax experience is a plus

This is intended to be a long-term contractor relationship rather than a temporary bookkeeping project. The contractor should maintain their own independent business or bookkeeping practice and be comfortable managing the work with limited supervision.

Because the engagement involves confidential financial and employee information, professional references and a background check will be required.

To apply, please include a brief description of your bookkeeping experience, your experience with Xero, payroll and HR administration, the types and sizes of businesses you currently support, and your hourly or monthly rate.

Pay: $35.00 - $50.00 per hour

Expected hours: 5.0 – 10.0 per week

Work Location: Remote