Senior Director of HR and Operations

Huckleberry Youth Programs•San Francisco, CA

1d•Hybrid

About The Position

Huckleberry Youth Programs (HYP) is seeking a Senior Director of HR & Operations to serve as a member of its Executive Team and lead the organization’s Human Resources, Information Technology, Data Systems & Evaluation, and Operations functions. The role strengthens the internal operations and infrastructure needed to advance HYP’s mission, supports organizational stability and impact, and promotes effective administration, internal communications, resource allocation, and a trauma-informed culture grounded in inclusiveness, integrity, innovation, diversity, and commitment to youth. The Senior Director provides strategic guidance to the CEO, Executive Team, and staff, and directly supervises the Director of Operations and the Director of Data Systems & Evaluation. The role also oversees contracted consultants and vendors across IT, facilities, data and evaluation, HR, audit, and compliance. The Senior Director leads people and culture strategy, including talent planning, employee relations, performance management, workforce planning, recruiting, onboarding, compensation and benefits strategy, retention, HR compliance, leadership development, and labor relations. In partnership with the Executive Team, the role fosters an equitable, inclusive, values-aligned work environment and serves as a senior advisor on people and culture matters. The position is the lead negotiator for collective bargaining agreements and labor-management relations. The role provides executive oversight of operations, facilities, administration, organization-wide technology strategy, and data and evaluation. Responsibilities include setting organizational operational direction and objectives, improving efficiency and collaboration, ensuring safe and well-resourced operating environments across sites, overseeing IT vendors and technology infrastructure, guiding cybersecurity practices and related change management, and ensuring data governance, HIPAA compliance, evaluation frameworks, and reporting systems meet funder, regulatory, and Board needs. The Senior Director also supports organizational performance and accountability, risk management, internal controls, insurance oversight, policy compliance, and timely decision-making. The position reports to the CEO and requires travel between HYP sites. It is full-time, exempt, and onsite/hybrid, with the possibility of hybrid work after the probationary period.

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 operational and HR functions advance that mission.
Deep commitment to equity, social justice, and trauma-informed organizational practice, with the ability to integrate accountability and care into leadership decisions.
Exceptional leadership skills and experience articulating an organizational vision and inspiring alignment with it.
Excellent written and verbal communication skills with 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 ability to work collaboratively with staff from diverse identities, backgrounds, and experiences.
Ability to implement systems, think strategically, solve problems creatively, and exercise good 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 calls for 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 or 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 across at least two relevant areas: Human Resources, Operations, or Technology/Data. The posting expresses a preference for this experience and notes 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 set goals, priorities, and culture.
Hire, train, supervise, mentor, and develop team members.
Foster an equitable, inclusive, values-aligned work environment in partnership with the Executive Team.
Lead talent strategy, culture, employee relations, performance management, workforce planning, recruiting, onboarding, compensation and benefits strategy, retention, and HR compliance.
Build leadership capacity through coaching, feedback, and accountability structures.
Advise the CEO and Executive Team on people and culture matters.
Serve as lead negotiator for collective bargaining agreements and labor-management relations.
Provide executive oversight of facilities, administration, operations, and organization-wide technology strategy.
Make IT vendor selection and management decisions within the organization's Signing Authority Matrix.
Ensure safe, effective, and well-resourced operating environments across HYP sites.
Oversee data governance, HIPAA compliance, evaluation frameworks, and data systems supporting funder, regulatory, and Board reporting.
Implement operational best practices that account for HYP's cross-county structure.
Set operational priorities in alignment with the CEO and Executive Team.
Develop policies, direction, and objectives for operational activities in partnership with department directors and team members.
Improve operational effectiveness and efficiency, strategic plan alignment, return on investment, interdepartmental collaboration, and productivity.
Coordinate with organizational leaders and staff to discuss issues, coordinate activities, and solve problems.
Lead organization-wide technology strategy, including vendor selection, infrastructure planning, cybersecurity practices, and internal change management.
Prepare reports for stakeholders, including the Board of Directors, with team leaders and the CEO.
Establish and maintain an integrated growth-planning framework that gives leadership real-time visibility into organizational health.
Assess organizational risk and implement measures to ensure compliance and mitigate risk.
Maintain HIPAA oversight, general compliance and risk management, insurance oversight, and internal controls.
Ensure compliance with relevant organizational policies, including record retention, technology use, employment and labor, and communications standards.
Exercise independent decision-making authority in the role’s domains and serve as an escalation point for timely organizational decisions.
Contribute as an engaged member of the Executive Team and participate in organizational initiatives and processes.
Maintain knowledge of developments and trends in youth services and nonprofit sectors.
Perform other duties as assigned.
Travel between HYP sites.