Managing Director, People Operations & Total Rewards

KIPP • New York, NY

2h • $165,000 - $200,000 • Onsite

About The Position

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.

Requirements

• 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.
• 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.

Responsibilities

• 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).
• 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.
• 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.
• 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).
• 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).
• Build strategy around, design, implement, and manage program plans, related timelines for system improvement, transition, and/or migration for widespread 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.
• 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.

Benefits

• Robust benefits include medical, dental, and vision.
• 403(b) retirement plan with a 50% match after 6 months.
• Generous Time-Off aligned with the school calendar
• Up to 12 weeks of 100% parental leave.
• Bright Horizon Back-up Child and Elder Care.
• Employer-paid Life Insurance and Short-term/Long-term disability.
• Employee incentives include an 8-week paid Sabbatical after 10 years, annual professional development funds, and tuition reimbursement.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed