Senior Payroll Operations Lead — Remote

Matcha; Northern (KY); Hybrid; USD 145,000 - 165,000; Full time

Benefits offered by this job

Health, dental, vision coverage

HSA options

FSA

Equity and 401(k)

Generous vacation

Parental leave

Fully remote within the US

Job summary

Pomelo Care is building its first in-house payroll team and seeking a Payroll Senior Manager to own end-to-end payroll for two entities across multiple cycles. You will lead the PEO-to-Rippling transition, partner with the People team and an outsourced vendor, and ensure tax filings, benefits withholdings, and internal controls are solid as we scale.

You will report to the Controller, work fully remotely within the continental US, and build a scalable payroll function while guiding a future

Qualifications

• Bachelor’s degree in Accounting, Finance, Business or equivalent.
• CPP certification is highly preferred.
• 7–8+ years of progressive, hands-on, multi-state and multi-entity payroll experience at a similarly sized organization.
• Experience with modern HRIS platforms (Rippling preferred) and leading system implementations or PEO transitions.
• Experience with payroll tax compliance, filings, and remittances.
• Strong internal controls experience and audit support.
• Expertise in benefits administration related to payroll (401(k), health/welfare deductions).
• Previous people-management experience or clear readiness to hire and lead a team.
• Strong Excel skills and ability to handle complex payroll data.

Responsibilities

• Own end-to-end payroll operations for two entities across multiple cycles with high accuracy.
• Lead the PEO-to-Rippling transition and collaborate with stakeholders during implementation.
• Ensure timely payroll tax filings and payments across jurisdictions.
• Oversee benefits-related payments and deductions.
• Maintain Rippling configuration, tax jurisdictions, and GL mappings.
• Serve as payroll administrator for Rippling and manage security, workflows, and integrations.
• Establish internal controls and segregations of duties in payroll processes.
• Coordinate with Accounting for proper coding and reporting in month/quarter/year-end closes.
• Answer employee pay inquiries with professionalism and confidentiality.
• Collaborate with People, Legal, and Accounting for audits and process improvements.
• Monitor and flag wage-and-hour compliance risks and remediation actions.
• Build scalable in-house payroll capabilities and documentation.
• Plan for hiring and onboarding a Payroll Coordinator/Specialist.

Skills

CPP certification

Payroll management

HRIS Rippling

Excel proficiency

Multi-entity payroll

Education

Bachelor’s degree in Accounting/Finance/Business

Tools

Rippling

General ledger systems

Job description

Pomelo Care is building its first in-house payroll team and seeking a Payroll Senior Manager to own end-to-end payroll for two entities across multiple cycles. You will lead the PEO-to-Rippling transition, partner with the People team and an outsourced vendor, and ensure tax filings, benefits withholdings, and internal controls are solid as we scale.

You will report to the Controller, work fully remotely within the continental US, and build a scalable payroll function while guiding a future