Senior Payroll Manager at Pomelo Care

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

About us

Pomelo Care is the leading virtual medical practice for women and children, providing care across pregnancy, postpartum, pediatrics, menopause, and perimenopause. We combine proactive, 24/7 clinical care with technology that helps us reach patients earlier, identify risks sooner, and deliver personalized care throughout their journey. Our team includes clinicians, technologists, operators, and problem-solvers working together to make high-quality care more accessible for families nationwide.

About The Role:

We are hiring our first internal Payroll Senior Manager as Pomelo Care transitions from a PEO to bringing all payroll services in-house and implementing a new HRIS (Rippling). This is a hands-on, high-visibility role for someone who can independently own accurate, compliant, multi-entity payroll for our organization of over 500 employees, while partnering closely with our outsourced payroll/implementation vendor during the transition and, longer term, building and leading an internal payroll team. This role is ideal for a detail-oriented payroll professional who enjoys both the operational rigor of running payroll and the strategic work of standing up a new function from the ground up.

This role reports to the Controller and can be based anywhere in the continental US.

What you'll do:

• Own end-to-end payroll operations across two legal entities, processing four payroll cycles per month with a high degree of accuracy and independence across both salaried and hourly employees
• Serve as the primary Finance internal owner of the PEO-to-Rippling transition, partnering with our People team and outsourced payroll vendor throughout implementation and the first year of operation to ensure a smooth, compliant cutover including data migration, and employee communication / training
• Ensure timely and accurate payroll tax filings and payments (federal, state, and local) across all applicable jurisdictions and entities
• Oversee timely and accurate processing of benefits-related payments and deductions, including 401(k)/retirement contributions, health and welfare premiums, and other employee benefit withholdings
• Maintain payroll system configuration in Rippling, including pay groups, earnings/deduction codes, tax jurisdictions, and general ledger mapping
• Serve as the payroll administrator for Rippling, owning system configuration, security/role-based permissions, workflow and approval routing, integrations, and troubleshooting for payroll-related modules
• Establish and maintain a strong internal control environment over payroll, including segregation-of-duties, approval workflows, access controls, and documented procedures
• Partner with Accounting to ensure payroll data is reconciled, accurately coded, and reflected in financial reporting, journal entries, and month-end/quarter-end/year-end close
• Act as the go-to resource for employee pay-related inquiries, resolving issues with professionalism, discretion, and a strong customer-service mindset
• Collaborate cross-functionally with the People, Legal, and Accounting teams to support audits, respond to data requests, and continuously improve payroll processes and controls
• Stay current on federal, state, and local payroll tax and wage-and-hour regulations, proactively flagging compliance risks and driving remediation
• Build the foundation for a scalable, internally-run payroll function, including documentation of processes and controls
• Prepare for and ultimately hire, onboard, and manage a Payroll Coordinator/Specialist to support anticipated growth

Who you are:

• Bachelor’s degree in Accounting, Finance, Business (or equivalent experience); a CPP certification is highly preferred
• 7 - 8+ years of progressive, hands-on, multi-state and multi-entity payroll experience at a similarly sized organization
• Admin-level expertise with modern HRIS platforms (Rippling is a significant plus), combined with direct experience leading system implementations and / or transitioning away from a PEO
• Direct experience with payroll tax compliance, filings, and remittances, and comfort serving as the organization's internal payroll compliance expert
• Experience implementing and maintaining strong internal controls and supporting audits
• Subject matter expertise in benefits administration as it relates to payroll (401(k), health/welfare deductions, leave payments, garnishments)
• Previous people-management experience or a clear readiness to hire, mentor, and lead a direct report as we bring payroll fully in-house.
• Strong Excel skills and a high comfort level working with complex payroll and general ledger data
• Patient, clear communication skills with the ability to explain payroll matters to employees with empathy and discretion, while building strong partnerships with internal stakeholders and external vendors
• Exceptional attention to detail, the ability to operate independently, navigate ambiguity, make sound judgment calls, and build processes from scratch

Why you should join our team

By joining Pomelo, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven startup that always puts the patient first. You will learn, grow and be challenged, and have fun with your team while doing it.

We strive to create an environment where employees from all backgrounds are respected. We value working across disciplines, moving fast, data-driven decision making, learning, and always putting the patient first.

Benefits and Perks:

• Comprehensive Health, Dental, and Vision coverage for employees and their families
• High deductible Health Plans with Health Savings Account (HSA) options
• Flexible Spending Account (FSA)
• Equity grant participation
• 401(k) program
• Competitive vacation policy
• 16 weeks paid parental leave
• Fully remote work flexibility (within the US)

Compensation:

The expected base salary range offered for this role is $145,000-$165,000. This role is also eligible for an annual performance bonus and equity, giving you an ownership stake in Pomelo’s mission. Actual compensation may vary based on relevant experience, skills, competencies, and certifications.

At Pomelo, we are committed to hiring the best team to improve outcomes for all mothers and babies, regardless of their background. We need diverse perspectives to reflect the diversity of problems we face and the population we serve. We look to hire people from a variety of backgrounds, including but not limited to race, age, sexual orientation, gender identity and expression, national origin, religion, disability, and veteran status.