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Number of Positions: 1

Position Overview

City Year seeks a Market President, Central Market to lead a portfolio of sites across Chicago, Detroit, Milwaukee, Kansas City, Memphis, Little Rock, Tulsa, Baton Rouge, and New Orleans. City Year is one 501(c)(3), and each site is a business unit with an Executive Director and team of staff and AmeriCorps members. The Market President manages, advises, and coaches Executive Directors to advance strong site performance, operational discipline, revenue growth, school and district partnerships, the experiences of staff and AmeriCorps members, and local board engagement.

Reporting to the Senior Executive Vice President and Chief Business Officer, the Market President serves as a senior executive and a member of City Year’s Management Executive Committee and is accountable for the Central Market's annual operating and long-term goals. This role connects the work of local sites with national strategy and shared services, ensuring that site needs are understood, priorities are translated into practical operating plans, and cross-functional support reaches sites in ways that improve performance and impact.

The ideal candidate is a seasoned, people-centered operator who can lead through complexity, coach senior leaders, use data to make decisions, manage financial and revenue performance across a portfolio, collaborate effectively across multiple functions, and build trust with school districts, donors, boards, staff, AmeriCorps members, and national colleagues.

Job Description

Minimum Qualifications

• 10 or more years of progressive senior leadership experience in a large, complex, multi-site, networked, or distributed organization.
• Demonstrated experience managing senior leaders, including coaching, performance management, talent development, and succession planning.
• Experience managing or overseeing complex budgets, revenue targets, operating plans, and performance metrics.
• Experience building relationships with external stakeholders, such as school districts, public agencies, funders, community leaders, or board members.
• Strong written and verbal communication skills, including the ability to communicate with senior internal and external audiences.
• Authorization to work in the United States.
• Ability to obtain and maintain required criminal background clearances for work involving school-age children.

Responsibilities

The Market President, Central Market will perform the following responsibilities:

Lead site management, operations, and portfolio performance

• Lead, manage, advise, and coach Executive Directors across the Central Market; set clear performance expectations and hold site leaders accountable for strong operations, mission delivery, staff leadership, staff and AmeriCorps member experience, and local stakeholder engagement.
• Translate enterprise priorities into clear annual and multi-year operating plans for the Central Market, with concrete expectations for revenue, expense management, corps size, school partnerships, and site-level performance.
• Monitor performance indicators across the portfolio; identify trends, risks, and opportunities; and support Executive Directors in developing practical plans to address performance gaps.
• Ensure that sites deliver City Year’s program with quality and fidelity, use student and school data to improve performance, and maintain a clear connection between operational decisions and student, school, and AmeriCorps member outcomes.
• Exercise appropriate decision authority across the portfolio, including decisions about priorities, resource allocation, performance interventions, and escalation, in partnership with Executive Directors and enterprise leaders.
• Use a portfolio-management approach to balance site-specific needs with overall market and organizational targets, including the ability to manage underperformance in one site while accelerating progress in another.
• Support sites through moments of financial, operational, or leadership pressure, coordinating the right headquarters partners while keeping the Executive Director positioned to lead locally.
• Partner with finance, planning, recruitment, analytics, district engagement, development, human resources, impact development, and other shared-service teams to align enterprise support with site needs, resolve cross-functional barriers, and ensure local leaders have the support needed to meet agreed-upon goals.

Drive revenue, district, and stakeholder strategy

• Partner with Executive Directors and development leaders to strengthen private revenue strategy, pipeline management, forecasting discipline, donor stewardship, and local board engagement.
• Support site leaders in setting ambitious but credible revenue plans based on historical performance, current pipeline, staffing capacity, local market conditions, and cross-site opportunities.
• Partner with district engagement, finance, and site leaders to strengthen school and district partnerships, address contract or public revenue changes and pursue a variety of public revenue strategies, and develop coordinated responses to major funding shifts.
• Identify funding synergies and multi-site opportunities across the Central Market, including opportunities that require collaboration between local sites and national teams.
• Represent City Year with external stakeholders when appropriate, while coaching and equipping Executive Directors to serve as the primary local leaders with their boards, funders, school districts, and community partners.

Strengthen financial discipline and annual planning

• Lead the Central Market through annual planning, including revenue planning, expense planning, corps size planning, workforce planning, and site operating goals.
• Ensure sites develop plans that align ambition with financial sustainability, including clear assumptions about public revenue, private revenue, staffing, corps size, and shared-service support.
• Work with finance and site leaders to understand changes in allocated costs, support-service costs, reserves, and site-level financial performance, and to communicate those issues clearly to local leaders and stakeholders.
• Support timely decision-making when revenue projections, district contracts, or local operating conditions require expense reductions, staffing changes, or changes to program scale.
• Promote consistent forecasting, accountability, and cost-management practices across the Central Market.

Develop Executive Directors and market leadership capacity

• Recruit, develop, coach, and retain a high-performing team of Executive Directors who can lead complex sites and strong local teams.
• Set clear expectations, provide regular feedback, and support Executive Directors in navigating complex stakeholder, board, revenue, culture, and operational issues.
• Create conditions for strong experiences of staff and AmeriCorps members across the Central Market, in partnership with Executive Directors and human resources.
• Build leadership capacity across the market by helping site leaders strengthen decision-making, communication, change management, and cross-functional collaboration.
• Serve as a senior escalation point for significant site challenges while maintaining appropriate local ownership and accountability.

Advance learning, continuous improvement, and cross-market collaboration

• Collaborate with other Market Presidents and the broader Market Operations team to identify patterns across sites, share promising practices, develop common standards, and improve the way City Year supports local markets.
• Partner with analytics, planning, and program leaders to test new approaches, monitor results, and apply learning to improve student, school, AmeriCorps member, and staff outcomes.
• Bring a clear field perspective into enterprise decision-making by communicating site opportunities, risks, and operating realities to senior leadership.
• Contribute to a culture of learning, disciplined execution, inclusion, accountability, and continuous improvement across City Year.

Preferred Qualifications

• Experience leading within an education, youth development, national service, nonprofit, government, or other mission-driven organization.Experience working with school districts, public-sector partners, or complex public/private funding models.Track record in fundraising, revenue generation, external relationship management, or sales, especially across corporations, foundations, major donors, or public partners.Experience working with boards or volunteer leadership bodies, including preparing leaders for board conversations and strengthening board/staff alignment.Experience leading through financial pressure, organizational change, leadership transitions, or complex stakeholder dynamics.Experience working in a complex, growing, multi-site organization.City Year, AmeriCorps, or national service experience is a plus.

Competencies

• Strategic Thinking: Identifies multiple pathways to address complex and ambiguous challenges; anticipates barriers and opportunities and develops practical plans to address them.
• Operational Leadership: Converts strategy into clear plans, routines, decisions, and accountability systems that improve execution across multiple sites.
• Financial Acumen: Uses budget, revenue, expense, and performance data to make sound decisions and communicate tradeoffs clearly.
• Developing and Empowering Others: Coaches senior leaders, builds talent, supports succession planning, and creates conditions for others to lead well.
• Collaboration: Works across functions and geographies, incorporates different perspectives, and aligns diverse stakeholders around shared goals.
• Understanding and Building Connection: Builds trust with colleagues, Executive Directors, boards, funders, school partners, and community stakeholders.
• Decision-Making: Makes timely decisions with incomplete information, balances local and enterprise needs, and adjusts as new information emerges.
• Learning: Seeks feedback, studies results, and uses evidence and reflection to improve self, teams, systems, and outcomes.

Physical Requirements

• Ability to sit for extended periods and occasionally stand or walk.
• Manual dexterity for typing, writing, and using standard office equipment.
• Ability to communicate clearly in person, by phone, video conference, and in writing.
• Ability to travel and move through office, school, event, and community settings as needed.
• Occasional lifting or carrying of materials weighing up to 20 pounds.

Working Conditions

• This is a full-time, exempt, remote role that may be based in Boston or in one of the Central Market sites: Chicago, Detroit, Milwaukee, Kansas City, Memphis, Little Rock, Tulsa, Baton Rouge, or New Orleans. Operates in a professional office, virtual, school-based, and community environment using standard office equipment. Requires regular travel to Central Market sites, City Year headquarters, schools, board or donor meetings, convenings, and other organizational events. Typical schedule includes weekdays, with occasional evening or weekend commitments based on site, board, donor, school, or organizational needs.Must have reliable internet access when participating in required virtual meetings or work.

Compensation

• The starting salary for this role is $215,000 annually, with final compensation based on experience, location, and internal equity.

Benefits