Payroll and Operations Specialist

ABOUT THIS ROLE

Pocketbook Strategies is seeking a full-time Payroll and Operations Specialist to manage payroll, insurance, and benefits for a portfolio of 10+ nonprofit and campaign clients. In this role, you'll process payroll across platforms like Gusto and Rippling, manage health insurance and fringe benefits (from broker negotiations to open enrollment), and oversee business insurance policies, all while serving as a point of contact who can explain complex administrative issues in plain terms.

The ideal candidate is well-organized and resourceful under pressure. They are comfortable with shifting client priorities, gathering input from multiple stakeholders, and solving problems in both routine and unusual situations.

Compensation:
The starting salary for this role is $70,000-$85,000 annually, commensurate with experience. This is a full-time, exempt position. Information about Pocketbook’s benefits plan can be found here. Role

Location:

This role is fully remote, with the expectation of attending team retreats and conferences 2-3 times a year. Supervision:
This role will report directly to Pocketbook’s Senior Director, Operations, Sade Bruce.

• Payroll System
  • Process payroll for 10+ clients on a timely basis, ensuring accuracy in wages, bonuses, overtime, and deductions.
  • Manage new hire, termination, and other employee change requests.
  • Set up, close, and transition payroll systems for clients using Gusto, Rippling, or Justworks, while meeting strict service delivery deadlines and proactively communicating with clients and vendors throughout.
• State Payroll Accounts
  • Set up and close state tax accounts.
  • Respond to and resolve state payroll tax notices, including filing overdue reports.

• Procure and manage health and ancillary insurance policies (e.g., medical, vision, short- and long-term disability) for 10+ clients.
  • Work with insurance brokers to secure new policies in accordance with client requirements and manage open enrollments each year thereafter.
  • Ensure health insurance information is added to payroll systems for accurate deductions and contributions.
  • Work with insurance companies to shut down plans that are no longer needed.
• Procure and manage fringe benefits (e.g., retirement, HSA or FSA, commuter benefits) for 10+ clients.
  • Work with providers to secure new benefits for clients from approved Pocketbook providers.
  • Manage existing benefits by ensuring new hires are enrolled, updating billing information, completing required compliance reports, and guiding clients through renewals.
• Procure and manage business insurance policies (e.g., directors and officers, general liability, workers' compensation) for 10+ clients.
  • Procure new lines of coverage, serving as the intermediary between brokers and clients for renewals, completing audits, walking clients through the claims process, and processing requested cancellations.

• Work with Pocketbook colleagues, third-party vendors, and clients to resolve service-related questions and technical issues.
  • Gather information from multiple sources to develop informed recommendations and solutions to big/small and interconnected/isolated problems both independently and on a team.
• Develop deep knowledge of assigned clients, financial software, and other Pocketbook service lines to solve cross-functional issues (internal and client-facing), improve service delivery, and resolve organizational compliance issues.
• Manage annual state reporting for assigned clients.
• Other duties as assigned.

Pocketbook Strategies is the finance and operations strategy firm for social movements and power building organizations.

Organizations across movement – be it an emergent campaign,…