Payroll Specialist

Drummond Woodsum•Portland, ME

38d•Hybrid

About The Position

Drummond Woodsum is seeking an experienced part-time Payroll Specialist to manage payroll for approximately 200 employees working across eight states. We are looking for someone with strong payroll knowledge who can independently manage the complete payroll cycle with accuracy, sound judgment, and a high level of discretion. The Payroll Specialist will work closely with Human Resources, Finance, and third-party vendors in a digital-first environment. In addition to processing payroll, this position will be responsible for processing, funding, and reconciling 401(k), HSA, and FSA contributions and identifying opportunities to strengthen payroll processes and controls.

Requirements

At least five years of hands-on payroll processing experience
Demonstrated experience independently processing multi-state payroll.
Working knowledge of federal, state, and local payroll requirements, wage and hour laws, payroll taxation, and year-end reporting.
Strong technology skills, including proficiency with payroll and HRIS platforms, vendor portals, electronic file transfers, and Microsoft Excel.
Demonstrated ability to learn and navigate new systems, troubleshoot data and system issues, and adapt to changes in technology and payroll processes.
Exceptional attention to detail, organization, and follow-through.
Strong analytical and problem-solving skills.
Ability to manage recurring, deadline-driven responsibilities independently.
Clear and professional communication skills.
Sound judgment and professional discretion when handling highly confidential information.

Nice To Haves

Experience processing payroll for an organization of comparable size and complexity preferred.
Experience processing and reconciling retirement plan deductions, loan repayments, HSA contributions, and FSA deductions preferred.
Experience with BambooHR preferred.

Responsibilities

Independently process regular, off-cycle, and final payrolls in accordance with firm policy and applicable federal, state, and local requirements.
Review and validate timekeeping records, compensation changes, reimbursements, deductions, taxes, and other payroll inputs.
Review payroll registers and supporting reports to identify and resolve discrepancies before payroll is finalized.
Maintain accurate payroll records, including earnings, taxes, deductions, contributions, adjustments, and supporting documentation.
Process payroll corrections and adjustments accurately and promptly.
Maintain accurate federal, state, and local tax withholding information for employees working across multiple states.
Process, submit, fund, and reconcile 401(k) deferrals, Roth and catch-up contributions, loan repayments, and applicable employer contributions.
Process, fund, and reconcile employee and employer HSA contributions and employee FSA deductions.
Investigate and resolve discrepancies between payroll records, internal systems, and vendor reports.
Coordinate quarter-end and year-end payroll processing, including reviewing payroll tax filings and Forms W-2 for accuracy.
Provide payroll and contribution records for internal and external audits, retirement plan testing, and other compliance requirements.
Respond to employee questions regarding pay, deductions, and payroll records.
Maintain the highest level of confidentiality when handling employee compensation, personal information, and firm financial data.