KIPP NYC – Managing Director, People Operations & Total Rewards

New York City

About KIPP NYC

Founded in 1995, KIPP NYC Public Schools is a nonprofit network of 18 free, public charter schools educating more than 9,400 students from the Bronx, Brooklyn, and Manhattan. We partner with families and communities to create joyful, academically excellent schools where every child grows up free to create the future they want for themselves and their communities.

From our first middle school, KIPP Academy in the Bronx, to today’s network of eight elementary schools, nine middle schools, and one high school, KIPP NYC has built a strong legacy of results and relationships. We believe that school should be both rigorous and joyful – and that every classroom should be a place where students are challenged, affirmed, and known.

Together with our KIPP Forward program, which supports more than 4,700 alumni through college, career, and life, KIPP NYC remains committed to delivering on the promise of educational excellence and equity at scale.

Learn more at https://kippnyc.org.

About the Opportunity

The Managing Director (MD) of People Operations & Total Rewards leads KIPP NYC’s People Operations function end-to-end for a total staff of close to 2,000 employees – ensuring accurate, timely, and high-trust delivery of payroll, benefits, leave administration, onboarding/offboarding, and People Ops systems and data. This leader drives integration and efficiency across payroll, benefits, and HR systems, sets governance and service standards, and modernizes workflows to reduce manual work while improving employee self-service and reporting.

This role reports to the Chief People Officer and works closely with Finance, Technology, and School Operations to ensure People Operations infrastructure supports KIPP NYC’s talent strategy, growth, and compliance responsibilities. The MD will lead a six person people operations team with coverage across payroll and timekeeping, benefits, leave administration, onboarding and offboarding, and people systems and lifecycle operations support.

Key Responsibilities

People Operations Strategy, Governance, and Service Standards

• Own the People Operations strategy and roadmap, including priorities for systems modernization, payroll operations, and total rewards delivery.
• Establish operational standards and service-level expectations (e.g., payroll accuracy, case response standards, HRIS data quality).
• Build team capacity and sustainable coverage by creating and maintaining standard operating procedures that reduce reliance on any single individual.
• Ensure interdependencies across the People team function and other departments are being met with appropriate benchmarks for data integrity, handoff completion, and process compliance (e.g. Technology, Finance and Schools).

Payroll Operations, Timekeeping, and Payroll Modernization

• Ensure accurate and timely payroll delivery, including governance for changes, approvals, and remediation planning.
• Lead payroll and timekeeping modernization and systems building, including managed services, optimization of payroll system, and policy work that improves accuracy and timeliness.
• Oversee and stabilize payroll workstreams (e.g., stipend and pay company coding) to protect financial integrity and audit readiness.

Total Rewards Operations (benefits, leave administration, and integrations)

• Oversee benefits administration and total rewards operations so programs support recruitment, retention, and pay equity.
• Guide benefits program operations and integrations (e.g., leave code updates, vendor/API integrations) to strengthen employee experience and accuracy.
• Provide input into organization-wide compensation and benefits frameworks and related communications.

Employee Life-Cycle Operations: Onboarding, Offboarding, and HRIS continuity

• Ensure onboarding and HRIS operations remain steady during transitions and staffing changes so schools and employees experience consistent service.
• Coordinate offboarding operations in partnership with cross-functional teams to support a reliable employee lifecycle experience (systems access changes, final steps, and service continuity).

People Operations Systems and Data Integrity

• Lead systems modernization to improve automation, reporting, and employee self-service (including any platform transitions and system upgrades).
• Use data to drive strategic initiatives on the People team, ensuring an employee’s lifecycle within the organization is tracked with accuracy.
• Oversee People Systems & Data initiatives (e.g., recruiting-to-HRIS migration, employee/org data cleanup, service ticketing rollout, data governance and dashboards).

Employee Training and Service Delivery

• Build strategy around, design, implement and manage program plans, related timelines for system improvement, transition and/or migration for wide-spread adoption. (e.g., UKG Pro transition).
• Build and implement training modules, webinars, and related articles on Hugo Hub in order to align and roll-out exceptional implementation of people related systems.

Vendor Management and Cross-Functional Leadership

• Lead vendor selection, implementation, and performance management for HR technology, managed services, and benefits partners.
• Partner with Finance, Technology, and School Ops on integrations, reporting, and governance so workforce data supports budgeting and planning.
• Oversee contractors/temporary support by defining scope, evaluating deliverables, and reducing dependency over time through process stabilization.

Candidate Profile

Qualifications & Experience

• 10+ years of progressive People Operations leadership, including meaningful ownership of payroll and benefits operations in a complex organization.
• Demonstrated success leading HRIS/system transitions, process modernization, and data governance initiatives (ideally UKG experience).
• Strong command of operational controls, audit readiness, documentation/SOP development, and service delivery models (case/ticketing helpful).
• Excellent cross-functional leadership skills with Finance, Technology, and Operations; confident executive presence and stakeholder management.
• Commitment to equitable, consistent employee practices and high-trust operational execution.

Leadership Approach

• A relationship-centered, visible leader who earns trust through presence, transparency, and integrity.
• Balances urgency for results with empathy for people – building a culture where feedback and care coexist.
• Systems-oriented, with the discipline to create clarity and the flexibility to adapt.
• Collaborative and humble; values diverse perspectives and creates space for others to lead.
• Deeply aligned with KIPP NYC’s mission of joyful, high-expectation education for all students.

Compensation & Benefits

KIPP NYC offers a competitive salary with a starting salary range of $165,000- $200,000, commensurate with experience, along with a comprehensive benefits package including medical, dental, and vision coverage; 403(b) retirement plan with employer match; generous paid time off; paid parental leave; and annual professional development funds.

This is a full-time, in-person role based in New York City.

Application Process

This search is supported by JoHo Talent Network and Lara Silvas Consulting. The application deadline is March 2nd, 2026, and applications should be submitted through the JoHo portal.

This role is intended for experienced, system-level people leader with a demonstrated record of leading HR strategy and driving strong results through others.

Equal Opportunity Statement

KIPP NYC LLC is an anti-racist organization that believes in the importance of being diverse, equitable, and inclusive. We are committed to creating a welcoming environment that includes employees with diverse backgrounds and experiences. We believe this enables us to better meet our mission and values while serving students and families throughout New York City.

BIPOC, women, gender-expansive, LGBTQIA+, veterans, and persons with disabilities are encouraged to apply. KIPP NYC LLC is an Equal Opportunity Employer and is committed to the principles of equal employment opportunity for all employees and applicants for employment.