Senior Director of HR and Operations

Huckleberry Youth Programs•San Francisco, CA

2d•$115,000 - $130,000•Hybrid

About The Position

The Senior Director of HR & Operations is a member of Huckleberry Youth Programs’ Executive Team and oversees the internal operations and infrastructure that support the organization’s stability and impact. The position leads the Human Resources, Information Technology, Data Systems & Evaluation, and Operations functions, providing strategic guidance to the CEO, Executive Team, and staff and stakeholders across those functions. The role promotes efficient administration, strong internal communications, effective resource allocation, and a trauma-informed, values-aligned organizational culture. As HYP’s senior people leader, the Senior Director guides talent strategy, culture, employee relations, performance management, workforce planning, recruiting, onboarding, compensation and benefits strategy, staff retention, and HR compliance. The position advises the CEO and Executive Team on people and culture matters, develops staff leadership capacity, and leads collective bargaining and labor-management relations. The role provides executive oversight of facilities, administration, organization-wide technology strategy, data governance, evaluation, and related compliance. It guides IT vendor selection and management, infrastructure planning, cybersecurity practices, HIPAA oversight, data systems, evaluation frameworks, organizational reporting, risk management, insurance oversight, and internal controls. The Senior Director partners with department directors and team members to set priorities, develop policies and objectives, improve efficiency and collaboration, and align operations with HYP’s strategic plan. The position exercises independent decision-making within its areas of responsibility, serves as an escalation point, contributes to Executive Team initiatives, and performs other duties as assigned. The position is full-time and exempt, working 40 hours per week. It is based onsite, with the possibility of a hybrid arrangement after the probationary period. The role requires travel between HYP sites and a DOJ/FBI background check.

Requirements

Strong leadership experience in a nonprofit setting.
Seven or more years in a formal people leadership role, with a demonstrated record of modeling equitable leadership for high-performing teams.
Understanding of and demonstrated commitment to HYP’s mission, including how HR and operational functions advance that mission.
Deep commitment to equity, social justice, and trauma-informed organizational practice, with the ability to balance accountability and care in leadership decisions.
Exceptional leadership skills and experience articulating an organizational vision and inspiring alignment with it.
Excellent written and verbal communication skills, including communication with a range of internal and external stakeholders.
Strong listening and relationship-building skills.
Excellent problem-solving, critical-thinking, and decision-making abilities.
Empathetic interpersonal and conflict-resolution skills, and the ability to collaborate with staff of diverse identities, backgrounds, and experiences.
Ability to implement systems, think strategically, solve problems creatively, and exercise sound judgment and self-control in ambiguous, high-stakes, or rapidly evolving circumstances.
Working knowledge of data governance, program evaluation methodology, and HIPAA-compliant data systems management.
Familiarity with IT infrastructure planning and technology vendor management; the role requires strategic oversight rather than hands-on IT execution.
Demonstrated experience in unionized and/or multi-site nonprofit environments.
Experience with standard software applications, including Paycom or a comparable HRIS platform, Microsoft/Google Workspace tools, and internet browsers.
Ability to travel between HYP sites.
Must pass a DOJ/FBI background check.

Nice To Haves

Ten or more years of progressively responsible experience in HR and leadership experience across at least two relevant areas: Human Resources, Operations, or Technology/Data. The posting states this is preferred and that equal experience across all areas is not required.

Responsibilities

Lead the Human Resources, Information Technology, Data Systems & Evaluation, and Operations functions; manage department directors and establish department goals, priorities, and culture.
Hire, train, supervise, mentor, and develop team members.
Foster a values-aligned work environment emphasizing equity, belonging, and inclusive decision-making.
Lead talent strategy, organizational culture, employee relations, performance management, and workforce planning.
Develop and implement practices supporting organizational culture, internal communications, recruiting, onboarding, compensation and benefits, staff retention, and HR compliance.
Advise the CEO and Executive Team on people and culture matters and serve as the lead negotiator for collective bargaining agreements and labor-management relations.
Provide executive oversight of operations, facilities, administration, and organization-wide technology strategy.
Oversee IT vendor selection and management, facilities, infrastructure planning, and cybersecurity practices.
Ensure safe, effective, and adequately resourced operating environments across all sites.
Provide executive oversight of data systems and evaluation, including data governance, HIPAA compliance, and evaluation frameworks.
Ensure organizational data systems support funder, regulatory, and Board reporting requirements.
Develop operational policies and objectives with department directors and team members, aligning operations with the strategic plan and improving efficiency, collaboration, and productivity.
Coordinate with leaders and staff to discuss issues, coordinate activities, and solve problems.
Lead internal change management for organization-wide technology initiatives.
Work with team leaders and the CEO to prepare reports for stakeholders, including the Board of Directors.
Establish and maintain an integrated growth planning framework that provides leadership with visibility into organizational health.
Assess organizational risk and implement measures to ensure compliance and mitigate risk.
Maintain oversight of HIPAA, general compliance, risk management, insurance, and internal controls.
Ensure compliance with HYP policies covering record retention, technology use, employment and labor, and communications.
Exercise decision-making authority within the role’s domains and serve as an escalation point for timely organizational decisions.
Contribute as an engaged member of the Executive Team and maintain knowledge of significant developments and trends in youth services and the nonprofit sector.
Travel between HYP sites and perform other duties as assigned.