Position Summary: With over $1.5 billion in operating expenses, the Office of Pupil Transportation (OPT) is the arm of the New York City Public Schools (NYCPS) dedicated to providing the students of New York City with safe, reliable transportation. Over 150,000 students utilize yellow bus service, with about 8,000 buses operating each day. School transportation services are provided to public, charter, non-public, and early childhood programs, and families.

The Senior Director of Human Resources will provide strategic oversight and leadership for human capital management supporting more than 200 OPT employees who ensure students safely and efficiently travel between their residences, schools, and/or programs. Serving as a key advisor to senior leadership, the Senior Director of Human Resources will drive initiatives to attract, develop, and retain top talent while fostering a diverse, inclusive, and high performance workplace culture. The role entails executive level responsibility for labor relations, progressive discipline, staffing strategies, and policy development for field and headquarters personnel.

The Senior Director of Human Resources will serve as a human capital resource, providing direct support to OPT's employees and promoting a diverse and supportive workplace. The Senior Director of Human Resources is responsible for overseeing all conduct related to labor relations, progressive discipline, and staffing of field and headquarters personnel. Performs related work.

Reports to: Senior Executive Director for Student Transportation, OPT

Direct Reports: Director of Human Resources

Key Relationships: Business Services Unit, OPT senior leadership and staff, the Division of Human Resources (DHR), Office of Equal Opportunity (OEO), Office of Labor Relations (OLR), Central leadership, Payroll, Timekeeping and personnel support, Legal Services, and Division of Financial Operations.

Responsibilities

Talent Planning and Recruitment

• Spearheads the development, implementation, and executive oversight of enterprise wide talent and succession strategies for a $1.5 billion transportation operation supporting more than 200 employees and 150,000 students daily, ensuring seamless alignment with operational demands and long term organizational goals.
• Directs office wide civil service hiring infrastructure, including high volume recruitment events, examinations, and compliance protocols, optimizing timelines and outcomes to secure top tier talent in a highly regulated environment.
• Oversees the creation, maintenance, and strategic refinement of an office wide job description bank to align with organizational goals.
• Designs and leads a robust office level onboarding program for full-time and part-time employees , incorporating best practices to ensure that they are able to begin successfully and long term retention.
• Strategically directs office wide recruitment efforts to hire full-time or part-time staff; leads outreach efforts, conducts executive level interviews, and makes final selection decisions as needed to support these efforts.
• Provides strategic guidance to each office leader to develop long term staffing plans, forecasting needs, and addressing talent gaps.
• Acts as a liaison for external and internal central office pipeline programs.
• Shapes OPT's overall staffing strategy, develops policy recommendations related to staffing, talent recruitment, retention, and succession planning, and presents to senior leadership.
• Leads recruitment efforts through strategically distributing job opportunities, managing postings, refining job descriptions, and overseeing interview processes to attract high caliber candidates.
• Establishes best practices and policies for hiring managers, including advanced strategies for effective job descriptions, hiring and job posting strategies; analyzes resumes regarding to civil service requirements.
• Conducts in-depth employee exit interviews, performs advanced human resource staffing analyses, and presents quarterly reports with actionable insights to executive leadership.
• Oversees the procurement and management of non employee workers, such as consultants, temporary staff, and interns; negotiates vendor contracts and monitors performance work agreements.
• Directs comprehensive training and development programs for all OPT staff levels, including mandatory safety/compliance training for drivers/mechanics, leadership development for supervisors, and civil service exam preparation support to build internal pipelines.

Human Capital Management

• Directs all staffing transactions in various NYCPS systems, including hiring, payroll, timekeeping, and benefits administration, ensuring accuracy and efficiency.
• Supervises a team in managing personnel functions and activities, ensuring compliance with applicable rules, regulations, laws, special circulars, as well as any other relevant directives and procedures while identifying opportunities for process improvements.
• Drives organization wide employee engagement and retention strategies, including pulse surveys, recognition programs, wellness initiatives, and career development pathways tailored to field (unionized) and headquarters staff, with measurable goals to reduce turnover in critical safety sensitive roles.
• Champions a positive, inclusive workplace culture by leading change management efforts, addressing organizational climate issues, and partnering with senior leadership to align HR practices with OPT's mission of safe, reliable student transportation.
• Partners with senior leadership to evaluate, redesign, and optimize personnel policies and procedures in alignment with budgetary constraints, fiscal stewardship, and the strategic imperatives of a $1.5 billion agency.
• Serves as primary strategist for collective bargaining preparation and ongoing contract administration, analyzing union proposals, developing counter strategies, and coordinating with OLR on high impact negotiations affecting union represented employees.
• Oversees labor management committees, facilitates joint labor management initiatives
• Monitors and informs staff about civil service exams and requirements, ensuring employees are in compliance with civil service laws and developing training programs to maintain adherence.
• Prepares resource materials and maintains a comprehensive, organization wide job description repository and compensation framework to attract and retain high caliber professionals while maintaining strict civil service compliance.
• Provides executive project management support for various HR related initiatives and high priority projects, including resource allocation and stakeholder coordination
• Leads coordination with relevant central and field staff to troubleshoot and problem solve for NYCPS applications related to human resources and finance, implementing systemic solutions.
• Manages high stakes emergency and special investigation matters, including confidential matters, with discretion and strategic resolution.
• Prepares reports, monitoring and tracking, utilizing various computer systems, and identifying areas for continuous improvement.
• Researches and crafts responses in an effective and timely manner to inquiries from other NYCPS offices for complex information requests related to lawsuits and Section 75 charges ensuring timely and defensible submissions.
• Shapes and presents OPT's overarching human capital strategy, including policy recommendations on staffing, recruitment, retention, and succession planning, directly to Senior Executive Director and central NYCPS leadership.
• Acts as senior advocate in all disciplinary proceedings, building and presenting cases for poor performance and misconduct, and driving outcomes that uphold accountability while mitigating risk.
• Oversees the coordination and direction of grievances for Office of Pupil Transportation employees, personnel performance conferences, Step I, II, III hearings, technical assistance conferences, and arbitrations.
• Represents OPT with high level employee and labor relations matters, including labor management meetings and conferences; makes recommendations to the Senior Executive Director for terminations and suspensions. Interprets and enforces all contractual agreements, rules, and regulations at the highest level; develops and implements enterprise wide HR policies that promote consistency, compliance, equity, and a high performance culture across field and headquarters operations.

Fleet Workforce Quality Oversight

• Provides oversight of the Fleet Workforce Quality function, ensuring rigorous screening, selection, and clearance of school bus drivers and attendants prior to service deployment.
• Directs the development and continuous improvement of driver and attendant recruitment pipelines and onboarding processes, ensuring alignment with safety, compliance, and operational requirements.
• Oversees the design and implementation of specialized training programs for drivers and attendants, including safety protocols, equipment operation, and compliance with all applicable laws and regulations.
• Establishes and monitors quality assurance standards and performance metrics for transportation personnel, ensuring consistency, accountability, and continuous improvement.
• Provides strategic oversight of workforce quality reviews and candidate eligibility determinations, ensuring only qualified personnel are approved to transport students.
• Provides executive oversight of quality assurance investigations into allegations of misconduct involving transportation staff, ensuring timely, fair, and compliant resolution of high risk cases impacting student safety.
• Directs the establishment and enforcement of enterprise wide safety and compliance policies for school bus personnel, including adherence to student safety standards and operational protocols.

Qualification Requirements:

Minimum

A master's degree from an accredited college in economics, finance, accounting, business or public administration, public health, human resources management, management science, operations research, organizational behavior, industrial psychology, statistics, personnel administration, labor relations, psychology, sociology, human resources development, political science, urban studies or a Juris Doctor degree from an accredited law school, and two years of satisfactory full-time professional experience in one or a combination of the following: working with the budget of a large public or private concern in budget administration, accounting, economic or financial administration, or fiscal or economic research; or in management or methods analysis, operations research, organizational research or program evaluation; or in personnel or public administration, recruitment, position classification, personnel relations, labor relations, employee benefits, staff development, employment program planning/administration, labor market research, economic planning, social services program planning/evaluation, or fiscal management. Eighteen (18) months of this experience must have been in an executive, managerial, administrative, or supervisory capacity. Supervision must have included supervising staff performing professional work in the areas described above; or

A baccalaureate degree from an accredited college and four years of satisfactory full-time professional experience in the areas described in "1" above, including the 18 months of executive, managerial, administrative, or supervisory experience, as described in "1" above.

An associate degree or completion of 60 semester credits from an accredited college and six years of satisfactory full-time professional experience as described in "1" above, including the 18 months of executive, managerial, administrative, or supervisory experience, as described in "1" above .

A four-year high school diploma or its educational equivalent approved by a State's department of education or a recognized accrediting organization and eight years of satisfactory full-time professional experience as described in "1" above, including the 18 months of executive, managerial, administrative, or supervisory experience, as described in "1" above.

A combination of education and/or experience equivalent to "1", "2", "3", or "4" above. College education may be substituted for professional experience at the rate of 30 semester credits from an accredited college for one year of experience. However, all candidates must have a high school diploma and at least two years of experience as described in "1" above, including the 18 months of executive, managerial, administrative, or supervisory experience, as described in "1" above.

Preferred

• Extensive experience (7+ years) in progressive HR leadership roles within large, unionized public-sector environments (e.g., NYC agencies, education, transportation, or municipal operations), including direct involvement in collective bargaining preparation, grievance/arbitration strategy, and union negotiations.
• Deep familiarity with NYCPS and Citywide HR/financial systems (e.g., Galaxy, NYCAPS, APRL, CityTime, CHRMS, PMS, PRISE) and civil service rules/regulations, including proven ability to navigate complex compliance, title classification, and personnel actions.
• Experience leading cross functional HR projects or change initiatives with measurable outcomes in retention, compliance, or operational efficiency.
• Strong analytical and project management skills, with proficiency in Microsoft Office 365 applications (especially Excel for workforce modeling) and data driven decision making.
• Commitment to fostering an inclusive, high performance culture aligned with NYCPS mission and values, including experience addressing equity in recruitment and development for diverse field based workforces.
• Ability to prepare and communicate clear and concise reports.
• Excellent communication, writing, and research skills.
• Experience in project management.
• Flexibility in managing competing tasks, working independently, and as a part of a team.
• Familiarity with NYCPS human capital systems, practices, rules, and regulations.
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