Director of Operations

Reports to: Vice President, Direct Cash Transfers

Start date: January 2027

Salary range: $120,000 to $135,000

Schedule: Full-time, 9:00 AM to 5:00 PM Eastern Time

Overview

Point Source Youth (PSY) is a national leader in the movement to prevent and end youth homelessness, with a planned annual budget of over $7 million. Founded in 2015, we partner with communities to scale direct cash transfers as prevention, our Targeted Housing Assistance Program, and a 24-month Direct Cash Transfers for Housing program, along with other evidence-based strategies that center the agency of young people, especially BIPOC and LGBTQIA2S+ youth. Our work includes research, policy, advocacy, fundraising, storytelling, movement building, narrative change, and implementation, culminating each year in our National Symposium on Solutions to End Youth Homelessness.

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 strong problem-solving skills 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. By managing complex workflows and building robust organizational systems, they will ensure our work is stronger, compliant, more equitable, and highly effective.

Responsibilities

Human Resources Leadership and 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.
• Lead the quarterly and annual review process and support performance management cycles, staff development, and implementation of effective HR practices, ensuring compliance and risk management processes are implemented and managed to the highest standards.
• Lead PSY's HR matters and create a thoughtful and supportive culture that advances our goals and mission.
• Assist with benefits administration, including enrollments, eligibility tracking, and liaison with our PEO.
• Lead employee offboarding, including documentation, exit interviews, final pay compliance, and benefits, in accordance with applicable employment law.
• Maintain accurate and confidential HR records, ensuring compliance with federal, state, and local employment laws.
• Complete and maintain 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, and determine how the PEO should best be utilized by the organization.
• Serve as the organization's primary administrator of ADP, managing payroll coordination with our accounting team, employee records, benefits administration, and reporting.
• Lead the timesheet process, including staff communication and coordination with the PEO.
• Ensure ongoing compliance with required staff trainings (e.g., cybersecurity training, sexual harassment training) and recommend and create expanded training programs.
• Update and maintain the operations and employee manuals.

Organizational Operations and 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.
• Initiate and facilitate training to ensure compliance excellence, risk management, and goal completion.
• Support cross-departmental projects by ensuring clear timelines, documentation, and communication pathways.
• Oversee all administrative and home office purchases.
• Support the annual audit and tax filings by acting as liaison between management, the Board, and the outsourced team for all required information and documents.
• Lead the annual insurance renewal process for the organization's insurance needs.
• Lead the organization's IT and cybersecurity risk management processes, working with an external IT partner.
• Develop and implement the organization's AI policy.

Finance Support and Administrative Stewardship (30%)

• Support leadership with preparation of the annual organizational budget and lead forecasting.
• Track expenses and monitor department spending.
• Lead profit and loss forecasting on projects and create a process for financial forecasting in 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.

Communication and 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 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 the Bill.com lead staff role, including processing invoices and completing consultant training.

90 Days

• Review current HR files, the employee handbook, state filings and registrations, and the 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 employee records and reporting; strengthen the use of BambooHR or confirm ADP as the sole system of record.
• Run a quarterly review cycle in BambooHR.
• Strengthen or launch a consultant contract tracking system with notifications 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.

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 the quarterly review process.
• Ensure agreed-upon key IT and risk management processes and systems are operational.
• Serve as a trusted, go-to partner for staff and leadership on HR, compliance, security, risk management, and operations matters.

Qualifications

• 7 to 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 an executive director, CEO, or president.
• Demonstrated experience managing state filings and registrations for a multi-state employer.
• Proficiency working with a PEO is required.
• 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 systems and IT security processes.
• Exceptional organizational, communication, and interpersonal skills.
• Excellent project management skills.
• Proven ability to manage confidential information and operate at the highest levels of discretion.
• Demonstrated commitment to equity.
• Ability to travel for team meetings, conferences, or partner engagements.
• Experience with BambooHR, Salesforce, Toggl, time tracking, and Bill.com is a plus.