Managing Director, People and Operations

City Year; Philadelphia (Philadelphia County); Hybrid; USD 125,000 - 135,000; Full time

Job summary

City Year Philadelphia is seeking a Managing Director of People and Operations to strategically align human, financial, and physical capital across the site. You will lead a 3-person department, drive talent development, and partner with cross-functional teams to advance site priorities.

The role requires strong change management, decision making, and collaborative leadership. Hybrid work includes three days in the Philadelphia office to support operations and stakeholder engagement.

Qualifications

• 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.

Responsibilities

• Lead the People and Operations department and coordinate with the Executive Leadership team.
• Oversee budget, finances, and site analytics; manage local reporting and resource utilization.
• Develop strategic workforce plans, talent acquisition, onboarding, and staff engagement.

Skills

Strategic thinking

Talent development

Change management

Communication

Stakeholder collaboration

Leadership

Education

Bachelor’s degree or equivalent experience

Master’s degree in HR or business administration (preferred)

Job description

Position Overview

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. 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, commensurate with experience. 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.

Application Requirements

Please attach the following to your application prior to submitting

1) Professional resume (No cover letter required.)

2) Separate document answering the following three (3) questions. To be considered, answer all three questions.

• Tell us about a time you coached and developed a high-performing staff member or team. What did you do, and what was the outcome?
• Describe a financial challenge your organization faced. How did you use data, innovation, and collaboration to approach it, and what was the result?
• How have you helped create a positive team culture and staff experience as a senior leader? What impact did those efforts have?

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 compliment 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.

Minimum Qualifications

• 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

Preferred 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

Competencies

• 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
• 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. You may participate in all benefit programs that City Year establishes and makes available to eligible employees, under (and subject to all provisions of) the plan documents that govern those programs. Currently, City Year offers medical, dental, vision, life, accidental death and dismemberment and disability coverage, Flexible Spending Accounts (FSA), and other benefits including 401(k) plan(s) pursuant to the terms and conditions of company policy and the 401(k) plan document. For more information, click here.

Employment at City Year is at-will.

City Year does not sponsor work authorization visas.

City Year’s dual mission is to expand educational opportunity for all students and develop the next generation of leaders through national service. Trained teams of City Year AmeriCorps members provide support to students, classrooms and the whole school. Schools that partner with City Year are up to two to three times more likely to improve in English and math assessments, and the more time students spend with AmeriCorps members, the more they improve on academic, cognitive and interpersonal skills— skills that help students thrive in school, college and career.

City Year’s 900 staff and 2,000+ AmeriCorps members work and serve in 29 communities across the U.S., including Boston (where City Year was founded in 1988 and is headquartered), Baton Rouge, Buffalo, Chicago, Cleveland, Columbia, Columbus, Dallas, Denver, Detroit, Jacksonville, Kansas City, Little Rock, Los Angeles, Memphis, Miami, Milwaukee, New Hampshire, New Orleans, New York, Orlando, Philadelphia, Providence, Sacramento, San Antonio, San José/Silicon Valley, Seattle/KingCounty, Tulsa and Washington, D.C. City Year also has international affiliates in the U.K. and South Africa.

A proud member of the AmeriCorps national service network, City Year is supported by AmeriCorps, local school districts and private philanthropy.

City Year has been designated a 4-star charity by Charity Navigator since 2003, putting City Year in the top 1% of non-profits nationwide for accountability, transparency and responsible fiscal management, and among the most trustworthy nonprofits in America.

At City Year, we sometimes say we work not only “at” City Year, but also “on” City Year, recognizing that the organization, like our world, is constantly evolving and changing. Two things that have never changed: our steadfast belief in the power of young people to change our world for the better; and our aspiration to create positive school and work environments where everyone feels a sense of connection, is supported to do their best work, and is able to learn, contribute, lead and create to their fullest potential.

As an equal opportunity employer, City Year is committed to providing employment opportunities to all qualified individuals and does not discriminate on the basis of race, color, ethnicity, religion, sex, gender, gender identity and expression, sexual orientation, national origin, disability, age, marital status, veteran status, pregnancy, parental status, genetic information or characteristics, or any other basis prohibited by applicable law.

Fair Labor Standards Act Family and Medical Leave Act Learn more at www.cityyear.org, City Year’s Facebook page, on X (formerly Twitter), and LinkedIn.