Payroll Manager (18 Month Contract)

Later•Boston, MA

10h•$100,000 - $110,000•Hybrid

About The Position

Later is hiring a Payroll Manager (Contract) 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. This is an 18-month contract with potential to convert to a permanent role.

Requirements

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

Nice To Haves

Experience with international payroll, EOR models, or platforms such as Deel (asset, not required)
Payroll Compliance Practitioner (PCP) certification (asset)

Responsibilities

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
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
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