About Howard Financial
Howard Financial is a full-service back-office solution for companies and entities with bookkeeping, payroll, and bespoke reporting needs that require accuracy, timeliness, and institutional-quality reporting without the burden of full-time staff.
We are an experienced team of bookkeepers and administrators with multiple decades of combined experience across industries allowing companies to focus on their core business while we handle the rest.
Founded in 2023, our team of 60 professionals supports ~40 clients across a diverse range of industries. We recently reached $5M of contracted ARR and are growing rapidly (over 150% MRR growth YTD).
Resumes must be submitted in English. Non-English resumes will not be considered.
LocationRemote (U.S.-based clients)
Position SummaryHoward Financial is seeking a Senior Paymaster with deep expertise in hospitality payroll to support a growing portfolio of restaurant, hotel, and food & beverage group clients. This role owns end-to-end weekly payroll operations across multiple entities and serves as a senior escalation point for compliance, accuracy, and client service.
The Senior Paymaster will manage complex payroll environments involving tipped employees, service charges, union and non-union workforces, and high-volume hourly staff. This role also provides leadership, process ownership, and continuous improvement as Howard Financial scales rapidly.
Key Responsibilities- Own and process weekly payroll for multiple hospitality clients, ensuring accuracy, timeliness, and full compliance with federal, state, and local regulations
- Review and validate timekeeping data, including hours worked, overtime, tipped wages, service charges, allocated tips, and shift differentials
- Ensure correct employee classification, job codes, pay rates, union rules, and payroll schedules
- Reconcile payroll registers, tax reports, and funding requirements; identify and resolve discrepancies proactively
- Act as senior point of contact for payroll audits, compliance reviews, and complex client issues
- Partner with HR and Accounting teams on onboarding, terminations, pay changes, and benefits deductions
- Prepare and deliver payroll reports, variance analysis, and insights for internal leadership and clients
- Lead, review, and mentor payroll staff; manage workflows and weekly deadlines
- Drive process improvements, documentation, and internal controls to improve efficiency and scalability
- Provide high-quality client service, managing inquiries and escalations professionally
- Maintain consistent weekly availability aligned with client payroll deadlines, with longer work commitments Monday through Wednesday
- 5+ years of progressive payroll experience, with significant hands-on experience as a Paymaster or Senior Payroll Specialist in the hospitality industry (restaurants, hotels, resorts, multi-unit F&B groups)
- Expert knowledge of hospitality payroll, including:
- Tipped employees and tip credit rules
- Service charges and tip allocation
- High-volume hourly payroll environments
- Weekly payroll cycles
- Union and non-union payroll structures
- Strong working knowledge of U.S. federal and state wage and hour laws, including FLSA and tip compliance
- Extensive experience with payroll systems such as ADP, UKG, Paylocity, or similar platforms
- Proven ability to manage multiple clients and tight deadlines simultaneously
- Exceptional attention to detail, accuracy, and time management skills
- Strong analytical and problem-solving abilities
- Demonstrated leadership experience, including reviewing work and managing schedules
- Professional English proficiency (written and verbal)
- Experience supporting multi-entity or multi-state hospitality groups
- Prior experience in an outsourced payroll or professional services environment
- Process improvement or payroll system implementation experience
This role is required to support Howard Financial’s rapid client growth, increasing payroll complexity, and weekly hospitality payroll demands. The Senior Paymaster will ensure accuracy, compliance, and client satisfaction while enabling the payroll function to scale efficiently.
