Senior Payroll Manager

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. 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) Why You Should Join Our Team By joining Pomelo, you’ll get in on the ground floor of a fast-moving, well-funded startup on a mission to improve outcomes for all mothers and babies. We cultivate a collaborative, patient-first environment where data drives our decisions and team members are challenged to learn, grow, and have fun together. We believe that solving critical healthcare problems requires perspectives as diverse as the communities we serve. Pomelo is committed to hiring and supporting a team of varied backgrounds, welcoming all applicants regardless of race, age, sexual orientation, gender identity and expression, national origin, religion, disability, or veteran status.