Head of Payroll and Benefits

Role Description: The Head of Payroll and Benefits is a full-time remote role responsible for overseeing all payroll and benefits-related activities for Toolkit For Founders and supporting founders who use the platform for payroll and benefits decisions. This role will design and manage internal payroll processes, ensure accurate and timely payroll runs, and maintain compliance with relevant tax and labor regulations across multiple jurisdictions. The Head of Payroll and Benefits will develop and optimize benefits programs, evaluate and negotiate with payroll and benefits vendors, and contribute expert input to the platform’s curated recommendations. Day-to-day tasks include monitoring payroll data integrity, resolving employee and client inquiries, preparing reports and analyses, implementing process improvements, and collaborating with leadership on compensation strategy and benefits design. The role will also provide thought leadership content, guidance, and best practices to help founders understand and select appropriate payroll and benefits solutions.

Qualifications: Experience leading payroll operations, including end-to-end payroll processing, multi-state or international payroll, and compliance with tax and employment regulations. Strong background in benefits administration, including health and wellness plans, retirement programs, leave policies, and vendor management. Proficiency with payroll and HRIS systems, data analysis, and reporting tools to ensure accuracy, scalability, and process efficiency. Knowledge of compensation structures, total rewards strategies, and best practices for small and medium businesses. Demonstrated ability to interpret and apply labor laws, regulatory requirements, and industry standards in practical, founder-friendly ways. Excellent communication and collaboration skills, with the ability to explain complex payroll and benefits topics clearly to non-experts. Proven experience working in a remote environment, with strong organizational skills and attention to detail. Bachelor’s degree in Human Resources, Finance, Business, or a related field; professional certifications (e.g., CPP, SHRM, CEBS) are a plus. Experience supporting startups or small and medium businesses, and familiarity with vendor selection and evaluation, is highly beneficial.