People Operations Specialist – Payroll & Benefits

Role Overview

• Coordinate payroll and contractor payments across vendors including TriNet, Rippling, and Deel, ensuring employees and contractors are paid accurately and on time
• Audit payroll data each cycle (new hires, terminations, compensation updates, benefits deductions) in partnership with Finance
• Maintain compliance with multi-state payroll regulations and support accurate processing of international contractor payments through vendor platforms
• Manage payroll-related correspondence including state tax notices and compliance documentation
• Troubleshoot payroll issues and resolve discrepancies with vendors and employees
• Partner closely with Finance to reconcile payroll reports, benefits deductions, and tax reporting
• Administer U.S. and Canadian benefits programs, including medical, dental, vision, disability, and retirement plans, partnering with vendors such as TriNet (U.S.) and Sterling Brokers / Open Access (Canada)
• Manage benefits enrollments, changes, and terminations in coordination with benefits vendors and within TriNet, Rippling, and BambooHR
• Serve as the primary point of contact for employee benefits and payroll questions
• Administer and track time-off policies and balances for employees and contractors across systems including TriNet, Rippling, and BambooHR
• Administer and track leaves of absence (LOA) including parental, medical, and statutory leaves
• Lead annual benefits renewals and vendor coordination, including supporting negotiations, in partnership with HR leadership and Finance
• Maintain accurate employee data across Rippling, BambooHR, TriNet, and Deel, ensuring alignment between HR, payroll, and benefits records
• Generate offer letters and onboarding documentation in partnership with Talent Acquisition
• Coordinate payroll and benefits setup for new hires and offboarding employees
• Conduct new hire onboarding sessions covering payroll, benefits, and HR systems
• Maintain compliance documentation including required trainings, policy acknowledgments, and regulatory postings
• Support ongoing maintenance of the Employee Handbook and HR policies
• Manage relationships with payroll, benefits, and HR system vendors
• Support ongoing administration and optimization of Rippling, including payroll-related workflows, deductions, and employee data
• Identify opportunities to streamline HR workflows, automate processes, and improve operational efficiency
• Create and maintain process documentation and SOPs for payroll, benefits, and HR operations
• Support internal reporting, audits, and compliance reviews related to payroll and benefits

Requirements

• 3+ years of experience in payroll, benefits administration, or HR operations in a multi-state U.S. environment
• Hands-on experience administering Rippling, including payroll workflows and employee data management
• Familiarity with Canadian payroll is highly preferred, but not required
• Experience coordinating payroll with vendors and auditing payroll data for accuracy
• Strong understanding of U.S. payroll regulations and benefits administration
• Experience serving as a primary point of contact for payroll or benefits questions
• Experience supporting HR compliance processes such as policy acknowledgments, required trainings, audits, or handbook updates
• Highly detail-oriented with strong analytical and problem-solving skills and the ability to manage sensitive employee data with accuracy and discretion
• Strong organizational with the ability to manage multiple systems and workflows
• Collaborative mindset and ability to work cross-functionally with Finance, HR, and Operations
• Proven ability to negotiate and manage vendor relationships
• Experience working in a remote or distributed company environment

Benefits

• Fully remote work from the comfort of your home
• Generous time off policy of 21 days (birthday included 🎉), 8 designated/floating holidays, 2 paid volunteer days, and 5+ sick days (dependent on state)
• Employer-sponsored health insurance plan through TriNet, including medical (United Healthcare), dental, vision, and life
• 401(k) retirement plan via TriNet's partner, Empower, with an employer match of up to 4%
• Reimbursement package for home office expenses and professional development, up to $1.5k
• Eligibility for employee equity plan (stock options)
• Wellness program with fitness and mindfulness classes
• Love your work and our mission of serving nonprofits!