Position Description

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 Deputy Director of Operations will be highly organized and detail-oriented and should take pride in providing clients and colleagues with the tools and information they need to make informed decisions and execute their responsibilities. A successful Deputy Director of Operations will enjoy digging into problems to develop novel yet straightforward solutions and will excel at building laypeople's understanding of nonprofit operations. 

Reports To: Senior Director of Operations

Location: Remote, with travel 2-3 times a year for organizational retreats

Hours: Full Time, Exempt

Compensation: The starting salary for this role is $80,000-$100,000 annually, commensurate with experience. This is a full time, exempt position.

Information about Pocketbook’s employee benefits can be found here.

Responsibilities

Internal

Inter-departmental Alignment and Vendor Management - 35%

• 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.

Client Facing

Client Business Insurance and Organizational Compliance - 25%

• 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.

Client Payroll, Benefits, and Human Resources - 40%

• Work with members of the Operations department to: 
• • 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. 

Prior Experience

Must Have

• 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.

Nice to Have

• 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. 

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 advisory, financial management, and financial operations and compliance services to a variety of leading political, civic, and social movement organizations.