Pocketbook Strategies · 5 days ago
Deputy Director of Operations
Pocketbook Strategies is seeking a Deputy Director of Operations to oversee and manage all aspects of the department’s day-to-day client-facing and administrative responsibilities. The role focuses on providing clients and colleagues with the necessary tools and information while developing solutions to operational challenges.
AccountingBookkeeping and PayrollComplianceConsultingFinancial Services
Responsibilities
Liaise with Pocketbook’s Finance and Compliance departments to:
Respond to their client-related, general subject matter, or software-related operations questions and issues; and
Develop solutions for internal cross-functional and client-facing problems
Serve as the point person for external department vendors and screen new department vendors to ensure Pocketbook partners with businesses that increase our value-add to our clients
Identify and develop solutions to departmental inefficiencies through new or refined processes, tools, and communication flows
Procure and manage business insurance policies, including directors and officers, general liability, workers’ compensation, and employment practices liability, for clients
Manage annual state reporting
Work independently, with vendors, and within the Operations department to resolve related questions and technical issues for clients
Prepare and execute contractor and subgrant agreements for clients, flagging and resolving potential issues before agreements are finalized
Transition or set up new payroll platforms, resolving payroll tax notices, setting up and shutting down payroll tax accounts, and filing overdue reports
Procure and manage fringe benefits — retirement, HSA or FSA, life insurance or short-term disability policies, or commuter benefits — for clients
Support the Senior Operations & HR Manager in procuring and managing medical, dental, and vision policies for clients
Operationalize the technical aspects of the HR policies they develop for clients
Proactively manage and work independently with vendors and software companies to troubleshoot technical issues for clients and assess vendor suitability for clients
Qualification
Required
4+ years of experience working at a 501(c) organization in an operations generalist role with increasing levels of responsibility
2+ years of people management experience
Ability to think abstractly about technical problems and implement solutions independently and on a team
1+ year of experience with nonprofit accounting or campaign finance compliance
Capable of adjusting to diverse client needs, shifting priorities, and varying levels of urgency
Superior project and knowledge management skills
Experience with Gusto/Rippling, Karbon, Airtable, Google Workspace, and QuickBooks
Preferred
Demonstrated experience working in a customer-facing role, juggling multiple client portfolios of various sizes
Professional or volunteer experience with community organizing, issue advocacy, or political campaigning
Working knowledge of 527 organizations and/or multi-entity nonprofit structures
Proven track record of building, managing, and implementing software integrations, connections, and workflows to improve efficiency
Experience working at a fiscal sponsor, professional services firm, or financial services company/start up