Job Description
Level is a learning technology company dedicated to helping students build real academic and life skills with confidence and joy. We combine proven curriculum principles with world class interactive design to make meaningful practice something students want to come back to, not something they struggle through.
We support what teachers, schools, and parents are already doing by increasing student engagement with high quality, standards aligned practice that reinforces classroom learning. That’s why we’re building:
For students: Rewarding and motivating learning experiences that meet students where they are to build real academic proficiency.
For educators: Tools that fit naturally into instruction and help students stay engaged while reducing teacher workload.
For parents: Activities that help your kid catch up or get ahead, build confidence, and minimize homework battles, whether learning at school or at home.
We are committed to helping every person maximize their potential and live a life of meaning. It’s a difficult problem that requires brilliant people and tremendous effort over time.
We are seeking a Senior Payroll & Benefits Specialist who can be the go-to expert for all things payroll, benefits administration, equity, and vendor/contractor payments. Reporting directly to the Director of People, you will own and scale our global payroll and benefits functions, ensuring accurate and timely payments while building strong financial controls and partnering closely with the People and Accounting teams to deliver a seamless employee experience. This is a high-impact, highly cross-functional role for someone who thrives on precision, process improvement, and building trust across an organization.
What You’ll Do
Key Responsibilities
Global Payroll Management
Own end-to-end payroll processing for employees across the US, Germany, and New Zealand, while serving as a key contact regarding payroll issues for global employees.
Ensure accuracy and compliance with federal, state, and international payroll regulations, including tax filings, withholdings, and statutory requirements.
Manage payroll-related benefits administration including HSA contributions, 401(k) deferrals/matching, and other deductions.
Troubleshoot and resolve payroll discrepancies, W-2 corrections, and employee inquiries.
Stay current on multi-jurisdictional payroll compliance requirements and proactively flag risks.
Oversee contractor payment cycles, including international contractor compliance (1099s, tax documentation, etc.).
Maintain organized records and documentation for all contractor payment activities.
Benefits Administration
Own end-to-end benefits administration across all regions, including US medical/dental/vision, 401(k), HSA/FSA, and ancillary benefits, as well as NZ and Germany statutory and supplemental benefit programs.
Serve as the primary point of contact for employee benefits questions, open enrollment, and life event changes.
Manages FMLA/CFRA, PDL, COVID, Discretionary Medical, Personal Leaves and Workers Compensation Case Management.
Manage relationships with benefits brokers and carriers, ensuring plan accuracy, timely renewals, and competitive offerings.
Maintain benefits compliance including ACA reporting, COBRA administration, and multi-jurisdictional statutory requirements.
Partner with the People team on new hire benefits onboarding and offboarding benefit terminations.
Payroll Accounting, Controls & Reporting
Serve as the primary point of contact for the Accounting team on all payroll-related payments and liabilities.
Collaborate with Accounting on monthly payroll reporting for the CFO and leadership team.
Establish and maintain strong internal controls over payroll, ensuring audit readiness and complete documentation.
Own payroll process governance, including implementing scalable systems and reducing manual risk as the company grows.
Manages yearly internal and external audits of payroll areas to include 401K and workers' compensation preparing all materials for auditors.
Cross-Functional Partnership
Serve as a strategic partner to the People team on compensation administration, benefits integration, employee onboarding/offboarding payroll workflows, and HR system data integrity.
Collaborate with Finance on payroll reporting, budgeting, forecasting, and audit.
Support contractor-to-FTE conversions from a payroll and benefits enrollment perspective.
Identify and implement process improvements to increase efficiency and reduce manual work.
Qualifications
Need to Have:
7+ years of experience in payroll and benefits administration, with at least 3 years managing multi-state and/or international payroll.
Demonstrated experience owning full-cycle benefits administration, including open enrollment, carrier management, and leave administration.
Strong knowledge of US federal and state payroll tax regulations, filings, and compliance.
Experience with global payroll and equity platforms.
Experience processing and managing vendor and contractor payments, including international contractors.
Familiarity with multi-jurisdictional benefits compliance (ACA, COBRA, FMLA, and applicable state/international requirements).
Exceptional attention to detail and a track record of accuracy in high-volume environments.
Strong communication skills and a collaborative, service-oriented mindset.
Ability to handle sensitive and confidential information with the utmost discretion.
Comfort working cross-functionally with Finance, People, and Legal teams.
Nice to Have:
Direct experience with Rippling as a primary payroll and HRIS platform.
Experience with self-funded health plan administration, including stop-loss coverage, TPA management, and claims analysis.
Experience administering equity plans, including partnering with Legal and Finance on compliance and reporting.
Experience with Carta or similar equity management platforms (grant administration, vesting, exercises).
Familiarity with German and/or New Zealand payroll and benefits compliance and statutory requirements.
CPP (Certified Payroll Professional), FPC (Fundamental Payroll Certification), or CEBS (Certified Employee Benefit Specialist).
Experience in high-growth startup, dynamic, and/or tech environments.
Experience identifying and implementing best-in-class payroll and benefits processes.
Experience supporting contractor-to-FTE conversions.
Background partnering closely with HR/People teams on compensation administration and employee lifecycle processes.