Payroll and Operations Specialist

Cim; Northern (KY); Hybrid; USD 70,000 - 85,000; Full time

Job summary

Pocketbook Strategies is seeking a fully remote Payroll and Operations Specialist to manage payroll, insurance, and benefits for 10+ nonprofit and campaign clients. You will process payroll across platforms (Gusto, Rippling, Justworks) and manage fringe benefits, health insurance, and business policies, reporting to the Senior Director, Operations.

Strong organizational skills are essential. The role is full-time, exempt, with a starting salary of $70,000–$85,000, and occasional team retreats

Qualifications

• At least 3 years of payroll, insurance, and benefits management in a 501(c) organization or political campaign.
• Familiarity with Gusto, Rippling, and other payroll platforms.
• At least 2 years of client or project management experience (managing 10+ clients).
• Ability to explain complex issues clearly to laypeople, verbally and in writing.
• At least 1 year of nonprofit accounting/finance or FEC campaign compliance.

Responsibilities

• Process payroll for 10+ clients across platforms with accuracy and timeliness.
• Manage health, dental, vision, and fringe benefits, including open enrollment.
• Oversee business insurance policies and broker negotiations.
• Serve as a primary contact to explain administrative issues in plain terms.
• Maintain and close state payroll accounts and respond to notices.
• Support client entity operations and cross-functional service delivery.

Skills

Payroll management

Insurance management

Benefits management

Tools

Gusto

Rippling

Justworks

Job description

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.

Responsibilities

Client Payroll Administration

• 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.

Client Insurance and Fringe Benefits

• 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.

Client Entity Operations

• 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, or an evolving institution – need sophisticated infrastructure, and that's why they come to us!

We exist to meet the needs of movements and campaigns and help build the operational infrastructure they need to survive the whiplash of momentum cycles, navigate growing complexity, and sustain themselves for the long haul. Our movement needs financial and operational services that they can trust both with the technical needs of their organization, and an aligned vision for the world that we want to build.

We provide fractional CFO/COO advisory services, outsourced accounting & bookkeeping, and financial operations and compliance consulting to a variety of leading political, civic, and charitable organizations.

Prior Experience

Must Have

• At least 3 years of payroll, insurance, and benefits management experience – including health insurance, business insurance, and fringe benefits – at a 501(c) organization or political campaign.
  • Familiarity with Gusto, Rippling, and other payroll technologies.
• At least 2 years of client or project management experience as demonstrated by:
  • Ability to adjust to diverse client needs, shifting priorities, and varying levels of urgency for 10+ clients at any given time.
  • Ability to manage multiple projects simultaneously from cradle to grave.
• Demonstrated ability to explain complex technical issues in simple terms to laymen verbally and in writing, and fully implement recommended solutions.
• At least 1 year of experience with nonprofit accounting/finance or FEC campaign finance compliance.

Nice to Have

• Professional or volunteer experience with community organizing, issue advocacy, or political campaigning.
• Certified benefits professional, or experience working at an insurance agency.
• At least 1 year of experience working at a fiscal sponsor, back office provider, or campaign finance compliance, or accounting firm.