Payroll Lead

The Role: 

We’re seeking a detail-oriented and proactive AMER Payroll Lead to join our growing team. In this role, you will take ownership of payroll across North America, the Caribbean, and Europe, processing and auditing payroll for a portfolio of 20+ countries, including multiple US states, Canada, and Puerto Rico, ensuring compliance with federal, state, and local regulations, and driving payroll automation in a fast-paced, remote-first environment. 

Responsibilities: 

• North American Payroll 

• Process bi-weekly, semi-monthly payroll for US (multi-state) and Canada through Rippling. 

• Process Puerto Rico payroll monthly. 

• Ensure compliance with all applicable payroll, wage, and hour laws across multiple jurisdictions. 

• Multi-Country Payroll 

• Take end-to-end ownership of payroll across a portfolio of 20+ jurisdictions, spanning North America (US, Canada, Puerto Rico), the Cayman Islands and Bermuda, the UK and Ireland, Guernsey and the Isle of Man, and continental Europe. 

• Process and manage payroll for all in-scope countries using Rippling and a mix of third-party providers (EY, Papaya Global, SD Worx, and local providers), ensuring accuracy in employee records. 

• Serve as the subject matter expert and primary escalation point for country-specific payroll regulations, tax laws, and compliance requirements. 

• Manage relationships with local in-country payroll vendors and advisors as needed. 

• Payroll Data 

• Maintain accurate employee records, pay rates, deductions, and tax information, and serve as the source of truth for employee data. 

• Respond to payroll-related inquiries from employees regarding pay, deductions, and benefits in a timely and professional manner. 

• Prepare payroll reports and documentation for audits and internal stakeholders, and assist with year-end tax filings including W-2s etc. 

• Lead payroll reconciliations and journal entries, and proactively resolve discrepancies. 

• Collaborate with the People team to ensure accurate employee classifications and pay rates across all jurisdictions. 

• Maintain confidentiality and data privacy in accordance with company policies and regulations. 

• Process Improvement 

• Drive continuous improvement and automation of payroll processes within Rippling. 

Skills & Experience 

• 3+ years of experience in payroll processing, with a strong focus on multi-country payroll. 

• Proven track record managing payroll across multiple jurisdictions simultaneously, ideally 8+ countries. 

• Bachelor’s degree in Finance, Accounting, Business Administration, or a related field. 

• Good understanding of US federal and state payroll regulations, tax laws, and compliance requirements. Working knowledge of Canadian, Caribbean, and European payroll regulations is a strong advantage. 

• Experience with payroll systems and HRIS platforms, ideally Rippling, EY, Papaya Global, and SD Worx. 

• High level of accuracy and attention to detail. 

• Experience working with third-party and in-country payroll providers. 

• Proficiency in Microsoft Excel (e.g., pivot tables, formulas, data validation). 

• Familiarity with benefits administration and 401(k) reporting. 

• Knowledge of payroll accounting and general ledger integration. 

• Preferred: experience managing multi-state US payroll and multi-country AMER payroll across 10+ countries. 

• Preferred: exposure to payroll in the Cayman Islands, Bermuda, or other Caribbean jurisdictions, and working knowledge of multiple European payroll jurisdictions. 

• Excellent written and verbal communication skills. 

• Highly organized and capable of managing multiple deadlines across time zones. 

• Comfortable working independently and in a distributed team environment. 

• Proactive, adaptable, and solutions-oriented mindset. 

Committed to Culture 

Specialty insurance helps others succeed by transforming uncertainty into predictable expense—empowering small businesses to do what was previously impossible. At Accelerant, we carry that same spirit into how we build our People function. 

We are Other-Obsessed. We design every People Ops process to support others in achieving their goals. We work from first principles with clear outcomes in mind. We say “yes” when we can. We give sustained maximum effort—every day—because enabling the success of others is our success too. 

We look for people who are wired for how we work: 

Ambiguity: you’re effective and comfortable in undefined, shifting conditions, without needing clarity or structure to be provided for you. 

Initiative: you spot problems, claim unowned work, and act before being asked. At Accelerant, the person pulls; the organization doesn't push. 

Pace: you’re energized by a fast-moving, high-intensity environment and can sustain high output over time.