Payroll Specialist - Hiring Immediately!

Prentice Organization•Portland, OR

3d•Onsite

About The Position

Prentice Hospitality Group and Foreside Development, based out of Portland, Maine, operates a collection of acclaimed restaurants, hospitality concepts, and community-driven projects. With a focus on craftsmanship, innovation, and genuine hospitality, we foster a collaborative culture where team members are empowered to grow and contribute to meaningful, experience-driven work. We are seeking a detail-oriented and experienced Payroll Specialist to support payroll operations across our multi-entity structure. This role is responsible for the accurate, timely, and compliant processing of payroll for a diverse workforce that includes salaried exempt employees, hourly non-exempt employees, and tipped workers across all operating entities. A core requirement of this position is the precise allocation of wages, tips, and employer obligations to the correct legal entity. The Payroll Specialist must ensure that tip income — including charged gratuities and cash tips — is reported, distributed, and allocated in strict accordance with applicable federal and state regulations, internal policy, and entity-level accounting rules.

Requirements

3+ years of payroll processing experience, with demonstrated experience supporting multi-entity or multi-location organizations.
Proficiency with a major payroll platform (e.g., ADP, Paycom, UKG, or equivalent); experience with multi-company or multi-EIN configurations strongly preferred.
Strong understanding of federal and state payroll tax law, including withholding on supplemental wages and tip income.
High degree of accuracy and attention to detail — particularly in entity-level coding, tip allocation calculations, and tax remittances.
Proficiency with Microsoft Excel (VLOOKUPs, pivot tables, reconciliation work).
Ability to handle sensitive payroll information with discretion and professionalism.

Nice To Haves

Paycom and Toast experience preferred, but not required.
CPP (Certified Payroll Professional) designation or active pursuit thereof.
Experience in hospitality, restaurant, or food & beverage industries where large-scale tip management is routine.
Familiarity with point-of-sale (POS) system tip data exports and integration with payroll platforms.
Experience supporting multi-state payroll compliance.

Responsibilities

Process full-cycle payroll for all entities on a weekly schedule, ensuring each employee's pay is accurately coded and posted to the correct legal entity.
Maintain strict segregation of payroll data across entities; proactively identify and correct any cross-entity coding errors before payroll is finalized.
Coordinate payroll cut-off schedules across multiple entities to ensure on-time direct deposit and check issuance.
Reconcile inter-entity payroll allocations each pay period and partner with Accounting to ensure proper journal entries are posted to the correct general ledger accounts.
Calculate, allocate, and record all tip income — including cash tips reported by employees, charged gratuities, and pooled tip distributions — ensuring amounts are attributed to the correct employee and the correct Prentice entity.
Monitor tipped employee earnings to ensure compliance with FLSA tip credit provisions; verify that tipped workers meet the minimum wage threshold after tip credits are applied, and process make-up pay as required.
Maintain clear documentation of tip pool agreements, distribution methodologies, and entity-level tip records to support audit readiness.
Process overtime, shift differentials, and variable pay accurately for hourly non-exempt employees across all entities, applying entity-specific pay rules and applicable state overtime laws.
Administer salary changes, LOA adjustments, deferred compensation, and bonus payments for exempt salaried staff, ensuring correct entity coding at every step.
Maintain working knowledge of federal and applicable state wage-and-hour laws, tip credit rules, and payroll tax regulations across all jurisdictions in which Prentice entities operate.
Support internal and external audits by producing entity-level payroll registers, tip allocation reports, and reconciliations on request.
Identify and flag potential compliance issues proactively, escalating to the Controller or HR Director with recommended remediation steps.
Maintain accurate employee records in the HRIS and payroll system, including pay rates, entity assignments, tip reporting elections, and deduction configurations.
Generate standard and ad hoc payroll reports for Finance, Operations, and entity leadership.
Participate in system implementations or upgrades, particularly as they relate to multi-entity payroll configuration and tip tracking functionality.