[Hiring] Director of Operations @Point Source Youth

Role Description

We seek an experienced collaborative, detail-oriented, and strategic leader to serve as our Director of Operations. The Director of Operations will lead PSY’s next stage of growth, with a strong emphasis on strengthening the organization’s infrastructure and building a culture of excellence, compliance, and effective risk management.

As the leader of the organization's human resources function and day-to-day operations, this role oversees the full employee lifecycle, state compliance, required filings, internal communications, administrative systems, and basic financial planning. The ideal candidate brings a systems-oriented approach, exceptional attention to detail, and a strong problem-solving skill set to support staff well-being and organizational growth. They will champion a culture centered on excellence, compliance, and risk management, ensuring that internal infrastructure keeps pace with our mission.

Responsibilities

• Human Resources Leadership & People Operations (30%)
  • Lead all core HR activities for the organization, serving as the primary owner of HR strategy, policy, and day-to-day administration.
  • Lead onboarding for all new hires, ensuring a consistent, compliant, and welcoming experience from offer through the first 90 days as well as leading a quarterly and annual review process.
  • Support performance management cycles, staff development processes, and implementation of effective HR practices.
  • Lead PSY’s HR matters and create a thoughtful and supportive culture in order to meet our goals and mission.
  • Assist with benefits administration, including enrollments, eligibility tracking, and liaison with our PEO.
  • Lead employee offboarding processes, including documentation, exit interviews, final pay compliance, and benefits offboarding, in accordance with applicable employment law.
  • Maintain accurate and confidential HR records, ensuring compliance with federal, state, and local employment laws.
  • Support the completion and maintenance of all required state filings and registrations related to employment, including multi-state employer registrations, unemployment insurance, and workers' compensation.
  • Ensure ongoing state-by-state compliance in conjunction with the PEO.
  • Serve as the organization's primary administrator of ADP, managing payroll coordination with our accounting team, employee records, benefits administration, and reporting.
  • Determine how the PEO should be best utilized by the organization.
  • Lead timesheet process and communication, including communications with the PEO.
  • Support staff development processes to achieve organizational goals and ensure compliance and risk management processes are implemented and managed to the highest standards.
  • Ensure ongoing compliance with required staff trainings (e.g., cybersecurity training, sexual harassment training) and recommend and create expanded training programs.
  • Update and maintain operations and employee manuals.
• Organizational Operations & Systems Management (30%)
  • Oversee and continually improve internal operations across teams, ensuring workflows are efficient and aligned with organizational priorities.
  • Develop and maintain organizational policies, procedures, and Standard Operating Procedures to ensure consistency, compliance, and operational clarity.
  • Manage vendor relationships, technology systems, facilities coordination, and organizational subscriptions.
  • Manage the creation, execution, and ongoing maintenance of all contracts and Memoranda of Understanding (MOUs) with partners and consultants.
  • Track and report on operational performance metrics; provide regular updates to executive leadership.
  • Lead organizational risk management processes, including compliance with nonprofit regulations, insurance updates, annual filings, and the creation of a staff training program.
  • Support cross-departmental projects by ensuring clear timelines, documentation, and communication pathways.
  • Initiate and facilitate trainings to ensure compliance excellence, risk management, and goal completion.
  • Oversee all administrative and home office purchases.
  • Support annual audit and tax filings by acting as a liaison between management, the Board, and the outsourced team for all required information and documents.
  • Lead annual insurance renewal process for the organization's insurance needs.
  • Lead the organization's IT and cyber security risk management processes working with an external IT partner.
  • Develop and implement the organization’s AI policy.
• Finance Support & Administrative Stewardship (30%)
  • Support leadership with preparation of the annual organizational budget and lead forecasting.
  • Track expenses and monitor department spending.
  • Lead financial forecasting of profit and loss analysis on projects and create a process for financial forecasting for future years.
  • Submit regular invoices to external parties as needed.
  • Process invoices using Bill.com; train consultants and staff on the platform and provide guides and tools as needed.
  • Maintain financial documentation and assist with audit preparation, grant reporting materials, and compliance requirements.
  • Collaborate closely with the external accounting firm to ensure accurate bookkeeping and financial reporting.
  • Track restricted and unrestricted funds in partnership with program and finance staff to ensure proper allocation.
  • Manage annual filings for state compliance with an outsourced team.
• Internal and External Communication & Cross-Functional Collaboration (10%)
  • Maintain and organize records and administrative documentation using platforms such as Google Drive, Slack, ADP, and Toggl.
  • Engage in internal working groups, strategic planning initiatives, and team culture development activities.
  • Provide scheduling support to leadership for both internal and external meetings.
  • Provide support for our Annual National Symposium on Solutions to End Youth Homelessness.
  • Other tasks as assigned.

Success Milestones

• First Month
  • Complete onboarding and training on all core systems, including ADP, and gain access to HR, finance, and compliance platforms.
  • Meet with leadership and key staff to understand organizational priorities, culture, and pain points.
  • Shadow or take over management of onboarding.
  • Map existing operational, HR, and finance workflows and begin identifying quick-win improvements.
  • Fully transition into Bill.Com lead staff person, including processing invoices and completing consultant training.
• 90 Days
  • Review current HR files, employee handbook, state filings/registrations, and compliance calendar to identify gaps or upcoming deadlines; resolve any outstanding gaps and confirm the organization is current and compliant.
  • Independently own the end-to-end onboarding and termination processes, with documented, repeatable procedures in place.
  • Fully transition into ADP and BambooHR administration, including using BambooHR for quarterly goal reviews, employee records, and reporting.
  • Strengthen or launch use of BambooHR (or confirm ADP as sole system of record), streamlining HR data management and reporting.
  • Strengthen or launch a consultant contract tracking system with notifications of when renewals are needed.
  • Revise or update key HR policies, including required training, AI usage, and others, to reflect current best practices and legal requirements.
  • Establish a recurring reporting cadence on HR and operational metrics for leadership and the Board.
  • Run a quarterly review cycle in BambooHR.
• Six to Twelve Months
  • Implement improved, scalable HR and operational systems and Standard Operating Procedures that support organizational growth.
  • Complete a full audit of state compliance, filings, and required staff trainings, with a proactive tracking system in place.
  • Lead the organization's operational efficiency, HR compliance, and cross-departmental collaboration.
  • Improve quarterly review process.
  • Serve as a trusted, go-to partner for staff and leadership on HR, compliance, security, risk management, and operations matters.
  • Ensure agreed upon key IT and risk management processes and systems are operational.

Qualifications

• Minimum of 7-12 years of progressive experience in nonprofit operations, HR leadership, or organizational management, including direct experience leading onboarding and terminations.
• Significant experience working directly with executive leadership including executive director, CEO, or president.
• Demonstrated experience managing state filings and registrations for a multi-state employer.
• Proficiency as a PEO is required.
• Experience with BambooHR is a plus.
• Strong understanding of nonprofit operational requirements, financial structures, compliance, and HR best practices.
• Strong working knowledge of federal and state employment law (FLSA, FMLA, EEO, state-specific requirements, etc.).
• Demonstrated experience implementing or improving organizational systems, workflows, and administrative tools.
• Proven ability to manage budgets, track financial data, and coordinate with accounting or financial partners.
• Demonstrated experience overseeing IT system and IT security processes.
• Exceptional organizational, communication, and interpersonal skills.
• Demonstrated commitment to equity.
• Ability to travel for team meetings, conferences, or partner engagements.
• Proven ability to manage confidential information and operate at the highest levels of discretion.
• Excellent project management and organizational skills.
• Ideally, experience with BambooHR, Salesforce, Toggl and time tracking, and Bill.com.
• Will work 9 AM-5 PM Eastern Standard Time.