Description

This is a Boston-based hybrid role with a 3-day per week in-office expectation.

Later is hiring a Payroll Manager to lead accurate, compliant, and scalable payroll operations across the US and Canada. Reporting to the Controller and partnering closely with Finance and People & Places, this role owns end-to-end payroll execution for 400+ employees across multiple jurisdictions, benefits programs, and third-party providers.

This is a hands-on leadership role for someone who thrives in complexity, brings strong judgment to time-sensitive work, and proactively improves systems and processes. While US payroll expertise is essential, this role also provides an opportunity to deepen Canadian payroll exposure alongside an experienced Payroll Specialist. 

What you'll be doing:
Technical / Execution

• Own and oversee end-to-end payroll processing for ~300 US and ~100 Canadian employees, ensuring accuracy, timeliness, and full regulatory compliance
• Review, administer, and approve semi-monthly payroll cycles, including bonuses, commissions, allowances, severance, leaves, and adjustments
• Maintain payroll system accuracy by managing employee lifecycle changes (new hires, terminations, role or compensation changes, leaves of absence)
• Ensure completion and accuracy of all payroll reconciliations, journal entries, and supporting documentation each pay period
• Lead year-end payroll processes across jurisdictions, including W-2s, 1095-Cs, T4s, T2200s, and related filings
• Prepare and submit required monthly, quarterly, and annual filings (e.g., Forms 941, EHT, Workers’ Compensation, unemployment insurance, WorkSafe BC)
• Serve as primary point of contact with payroll vendors, benefits providers, and EOR partners to resolve discrepancies and ensure SLA adherence
• Administer US and Canadian benefits programs, including 401(k) enrollments, contributions, audits, and employee inquiries

Team / Collaboration

• Provide day-to-day oversight and support to the Payroll & Benefits Specialist, ensuring consistency, accuracy, and knowledge sharing
• Partner closely with Accounting and FP&A to deliver clean payroll data, reconciliations, and reporting that support close and forecasting cycles
• Collaborate with People & Places on employee experience, benefits administration, and policy alignment
• Respond to payroll-related inquiries from employees, auditors, and government agencies with professionalism, discretion, and clarity

Research/Best Practices

• Proactively identify payroll risks, inefficiencies, or compliance gaps and implement improvements before issues escalate
• Document, refine, and improve payroll workflows to increase efficiency, scalability, and audit readiness
• Stay current on US and Canadian payroll regulations, tax changes, and best practices, applying updates pragmatically and accurately

What success looks like:

• Payroll is processed accurately and on time, every cycle, with zero material errors
• All statutory filings, remittances, and year-end obligations are completed on schedule and without compliance issues
• Payroll audits are smooth, well-documented, and require minimal follow-up
• Payroll data is trusted by Finance, FP&A, and leadership to support decision-making
• Processes are clearer, more efficient, and more resilient than when you started
• Employees experience payroll and benefits as reliable, responsive, and easy to navigate

Requirements

What you bring:

• 5+ years of full-cycle payroll experience, including hands-on ownership in a multi-state US environment
• Demonstrated experience processing payroll for 200+ US employees across multiple states
• Working knowledge of Canadian payroll processes and statutory requirements (direct experience preferred; willingness to learn required)
• Proven experience using ADP Workforce Now or comparable enterprise payroll systems
• Strong understanding of payroll compliance, taxable benefits, and employment standards legislation
• Track record of managing payroll audits, reconciliations, and regulatory filings independently
• Hands-on experience with month-end reporting for Accounting teams, as well as high level of inter-department communication skills
• High level of judgment, integrity, and discretion when handling sensitive and confidential information
• Strong analytical skills with the ability to identify discrepancies, assess risk, and resolve issues efficiently
• Intermediate proficiency in Google Sheets and Docs, including reconciliations and reporting
• Continuous-improvement mindset with experience streamlining payroll workflows or systems
• Experience with international payroll, EOR models, or platforms such as Deel (asset, not required)
• Payroll Compliance Practitioner (PCP) certification (asset)