US Payroll Specialist | WFO

Cloudstaff Pty; Masamat, Makati, Eastern Manila District, Canlandog; On-site; PHP 4,459,000 - 6,369,000; Full time

Job summary

Cloudstaff is hiring a US Payroll Specialist to own end-to-end payroll for four Illinois home care agencies. This role partners with agency leadership to consolidate payroll, ensure compliance, and manage filings and tax payments.

The position requires deep US payroll expertise, QuickBooks Desktop proficiency, and comfort working with multi-entity setups across FEINs. Knowledge of 941s, IL payroll laws, and local Chicago requirements is essential.

Qualifications

• Proven, hands-on US payroll experience including processing, filings and compliance.
• QuickBooks Desktop proficiency is required.
• Experience with multi-entity payroll or comparable complexity.
• Knowledge of federal/state payroll tax requirements including 941s and IL unemployment.
• Strong verification and reconciliation skills with attention to rates, hours and totals.
• Ability to handle IRS/state payroll correspondence professionally.

Responsibilities

• Run full bi-weekly payroll cycle for four agencies accurately and on schedule.
• Verify payroll source data (WellSky hours) before processing, and post payroll to QuickBooks Desktop.
• Perform post-payroll checks to ensure payments, rates, and hours align with billing.
• Own Form 941s end-to-end and manage corresponding tax payments; handle IL unemployment filings.
• Own year-end processing and filings, including W-2s.
• Track and administer Illinois and local paid leave requirements; maintain policy compliance.
• Administer FMLA tracking and documentation.
• Handle payroll-related IRS/state correspondence and notices with proper responses.
• Administer Illinois Secure Choice retirement reporting and contributions.
• Maintain clean payroll records and reconciliations across all entities; flag discrepancies.
• Serve as primary contact for payroll questions from agency staff.

Skills

US payroll

Payroll processing

Tax filings

Compliance

Multi-entity payroll

Illinois payroll experience

Attention to detail

Tools

QuickBooks Desktop

ADP platform

WellSky

Job description

Work-From-Office is a setup based in Angeles/Makati/Ortigas/Bacolod

We are hiring a US Payroll Specialist to own payroll end to end for a group of four Illinois home care agencies. This is a position that works day to day with the agencies' ownership and operations team.

Payroll is currently fragmented across several people. This hire consolidates it under one accountable owner: processing, filings, compliance, and verification. The right candidate needs little training and can take over a live, high-volume payroll with confidence.

Scope

• Approximately 400 employees across 4 agencies (separate entities/FEINs)
• Bi-weekly pay cycles for every agency
• W-2 employee payroll (contractor/1099 processing may remain with existing staff)

Responsibilities

• Run the full bi-weekly payroll cycle for all four agencies accurately and on schedule
• Verify payroll source data (WellSky hours) before processing, and push finalized payroll to QuickBooks Desktop
• Perform post-payroll checks every cycle: confirm all payments went out correctly, pay rates are accurate for each employee, and payroll hours match billing hours
• Own the 941 process end to end: prepare and file the federal and state Form 941s and manage the corresponding tax payments, so both the payment and the filing of the 941s sit with this role; also handle Illinois unemployment filings
• Own year-end processing and filings, including W-2s
• Track and administer PTO, including Illinois and local (Chicago/Cook County) paid leave requirements and company policies
• Administer FMLA tracking and documentation
• Handle IRS and state payroll correspondence and notices, including drafting responses (with written authorization where required)
• Administer Illinois Secure Choice retirement program reporting and contributions
• Maintain clean payroll records and reconciliations across all four entities, and flag discrepancies to ownership promptly
• Serve as the point of contact for payroll questions from agency staff

Requirements

Proven, hands-on US payroll experience covering processing, tax filings, and compliance (no minimum years, but the experience must be deep enough to run this payroll with minimal training) QuickBooks Desktop proficiency (required) Experience with multi-entity payroll (multiple FEINs) or comparable complexity Working knowledge of federal and state payroll tax requirements, including quarterly 941 filings and year-end reporting Strong verification and reconciliation skills, with a detail-first approach to rates, hours, and totals Ability to handle IRS and state agency correspondence professionally Availability for at least a half-day overlap with US Central business hours Preferred Home care or healthcare industry payroll experience Illinois payroll experience (state unemployment, IL Secure Choice, Chicago/Cook County paid leave ordinances) ADP payroll platform experience Experience with WellSky or similar home care scheduling/billing systems