Managing Director, People and Operations

City Year Philadelphia (CYP) is seeking a Managing Director of People and Operations (MD POps) who is responsible for strategically maximizing the alignment and leveraging of site CYP human, financial, and physical capital. The Managing Director, People and Operations reports to the Sr. Vice President and Executive Director and manages a department of three, including two direct reports.

About the role

The ideal candidate is highly strategic with a proven history of attracting, developing, empowering, and retaining top talent; providing clear, motivating, and professional communication skills; successfully managing change, thinking and acting strategically, demonstrating excellent decision-making skills, high accountability, and a highly collaborative approach. A customer orientation to support staff, Student Success Coaches, board members, and others is essential while innovating to creatively access resources and create user-friendly systems for people and financial operations. The MD POps will be an innovator who fosters that spirit within their department and throughout the site.

The starting salary range for this role is $125,000 - $135,000 annually. The anticipated start time frame for this position is September 2026. This role is a hybrid position with an average of 3 days in the City Year Philadelphia office to support operational needs, collaborate cross-departmentally, and engage with the People and Operations Department.

Responsibilities

• Department/Site Strategy and Initiatives
  • Serve on the Executive Leadership team of managing directors and the Site Leadership Team of Directors.
  • Strategize to collaborate and advance short and long-term site priorities, to build culture and climate within the site, and to implement change management best practices as needed.
  • Develop and advance department strategy, priorities, and finances.
  • Lead the coaching, development, performance management, and team engagement among the People and Operations department.
• Budget and Finance Management
  • Staff the Site Board Finance Committee and lead all local financial and human capital reporting.
  • Oversee the annual budget process, financial reforecasting, and analytics to maximize resource utilization.
  • Monitor site financial progress and recommend adjustments as needed.
  • Ensure that all financial systems comply with applicable policies and operate smoothly, inclusive of revenue-generating programs and contracts.
  • Cultivate local vendor partnerships to support communities City Year serves as in-kind product and service providers and as general funding supporters.
• Human Resource and People Experience Oversight
  • Workforce Planning - Partner with executive director to develop strategic workforce planning initiatives, including staff professional development plan, succession planning map, and staffing structure adjustments as needed.
  • Staff Engagement - Continuously innovate plan for engaging staff team of 30-40 and annual Student Success Volunteer cohort of 130, using site and national data to inform strategies; cultivate an informed community by partnering with Executive Office to deliver clear and transparent internal communications on key topics.
  • Talent Acquisition and Onboarding - Develop strategies to seek and develop new partnerships for sourcing talent; lead department staff to facilitate full local hiring and onboarding processes, resulting in effective and timely hires.
  • Employee Relations - Partner with City Year Headquarters and local staff to investigate and address grievances, concerns or misconduct or accommodation requests of staff or Student Success Coaches; coach and support staff managers in performance improvement plans, coaching plans, and terminations.
• Administration and Compliance
  • Ensure all org-wide policies are executed at the local level; ensure that federal, state, local, and partner district policies are followed and that all background checks are conducted and monitored appropriately.
  • Comp and Benefits Liaison – Serve as lead site liaison to City Year Headquarters on local matters related to compensation and benefits; cultivate local incentive and reward sources that complement org-wide benefits.
• Site Operations, Safety, and Facility Management
  • Site Technology – Co-design the strategy for site technology investments with site and headquarters staff; collaborate on resourcing strategies to fund technology investments; lead site AI learning and integration in collaboration with national headquarters.
  • Safety - Partner with City Year Headquarters and local staff to address safety, health, and emergency crisis concerns; support the integration and implementation of all local and state safety requirements into office policies and procedures.
  • Facility Management – Assess and continuously improve all office workspace policies, procedures, and systems, including flexible work policies; serve as site lead for property management and related lease negotiations as needed; collaborate with relevant staff to fund office investments.

Requirements

• Bachelor’s degree or equivalent experience required.
• Minimum 7 years of team management, coaching, and development with a strong record of results.
• Authorized documentation to work in the United States.
• Ability to pass criminal background checks as required for working with school-age children.

Qualifications

• Master’s degree in human resources and/or business administration.
• Professional HR certification a plus (SHRM-CP or SHRM-SCP; PHR or SPHR).
• Experience with local and national community service.
• Background in human resources, finance, and/or operations.
• Strong technical acumen and ability to utilize multiple technology platforms, as well as coach others towards utilization/interpretation.
• Proven success in developing talent through performance plans, reviews, and leadership opportunities.
• Track record of building and maintaining productive relationships with key stakeholders.
• Ability to use progress and outcome data to inform team management.
• Tenacity and flexibility in the face of challenges while working in demanding environments.
• Strong record of building and maintaining productive relationships with key stakeholders.
• Experience reading financial statements and reports, building and using financial models to forecast.
• Success building and implementing systems.

Skills

• Communication: Understands audience to deliver convincing and well-organized presentations; facilitates effectively to move initiatives forward; uses brand to convey mission and goals; coaches others.
• Team Leadership: Successfully leads diverse teams of individuals to achieve results; sets priorities and appropriately delegates tasks; holds people accountable - proven ability to engage in cognitive conflict and hold staff accountable towards their performance goals.
• Talent Development: Maintains intellectual capital; shares leadership opportunities; supports talent development and staffing organization-wide; proven success managing diverse teams towards a common goal.
• Decision Making/Judgment: Understands and manages organizational decision-making, including integration across network/departments; effectively communicates, manages, owns, and champions decisions being implemented.
• Strategic Thinking and Planning: Develops and translates strategies into objectives, action plans, and measurements, which build the capacity of the site/department.
• External Relationship Development: Takes initiative in establishing new partnerships and external opportunities; ability to secure commitments to organization.

Working Conditions

• Occasional travel required, including to local partner schools and events, and to other City Year sites and national conferences.
• This role requires extensive stationary focus during extended discussions, presentations, and virtual calls.
• Occasional lifting or carrying of materials (e.g., event supplies, training materials) up to ~20 lbs.
• Works a hybrid schedule, including minimum 2-3 days in-person, with occasional periods of longer in-person commitments.
• Follows a generally flexible business hour schedule of 9:00 a.m. – 5:00 p.m. with occasional required evening and weekend commitments.
• Must have reliable internet access when participating in any required virtual meetings or trainings.

Benefits

• Full-time employees will be eligible for all benefits including vacation, sick days, and organization holidays.
• Medical, dental, vision, life, accidental death and dismemberment, and disability coverage.
• Flexible Spending Accounts (FSA).
• 401(k) plan(s) pursuant to the terms and conditions of company policy and the 401(k) plan document.

Employment at City Year is at-will.