Demo

Chief Executive Officer

Pathways High Milwaukee
Milwaukee, WI Full Time
POSTED ON 4/22/2026
AVAILABLE BEFORE 5/21/2026
Now Hiring: Chief Executive Officer Full-time beginning 7/1/26, reporting to the Pathways High Governance BoardCandidates should send resume and cover letter to careers@pathwayshigh.org


The Chief Executive Officer (CEO) serves as the top leader of Pathways High School and is responsible for ensuring the long-term success, sustainability, and strategic direction of the organization. The CEO works in close partnership with the Board to set vision, establish priorities, and ensure that key organizational goals are executed with urgency and fidelity.


The CEO has primary responsibility for external leadership, organizational strategy, financial sustainability, enrollment growth, charter accountability, and overall performance of the school. The CEO directly oversees the Principal and ensures strong execution in instructional leadership, school culture, and daily operations.


This role is distinct from the Principal in that it focuses on organizational leadership, strategy, and outcomes, rather than day-to-day school management.


Reporting Structure:

Reports to: Board of Directors

Supervises: Lead School Administrator, Director of Business Operations, and other designated leadership roles


Core Responsibilities:


Strategy, Vision, and Organizational Leadership

  • Lead the development and execution of short- and long-term strategic plans aligned to the school’s mission and charter goals
  • Establish clear organizational priorities with measurable outcomes related to enrollment, academic performance, and financial sustainability
  • Monitor progress toward strategic goals and ensure timely adjustments based on data and performance
  • Ensure strong alignment between board priorities, leadership actions, and school outcomes


Board Partnership and Governance

  • Serve as the primary liaison to the Board, ensuring clear, consistent, and transparent communication
  • Provide regular updates on key metrics, including enrollment, financial health, academic outcomes, and organizational performance
  • Support the Board in governance responsibilities, including policy development, compliance, and strategic decision making
  • Ensure the Board has the information needed to make informed decisions while maintaining appropriate governance boundaries


Charter Accountability and Compliance

  • Ensure full compliance with charter authorizer expectations, state and federal regulations, and reporting requirements
  • Lead the charter renewal process and ensure strong performance against all accountability metrics
  • Oversee the development and submission of required reports, grants, and compliance documentation
  • Monitor organizational performance to ensure alignment with charter goals and performance frameworks


Enrollment, Marketing, and Growth

  • Lead the development and execution of a comprehensive student recruitment and enrollment strategy
  • Establish clear enrollment goals and monitor progress through regular data analysis and reporting
  • Oversee marketing and communication strategies to strengthen the school’s brand and visibility
  • Ensure an “all hands on deck” approach to enrollment that engages staff, board, students, and families


Financial Leadership and Sustainability

  • Oversee the development and management of the school’s budget in partnership with finance staff and the Board
  • Ensure financial sustainability through strong fiscal management, enrollment growth, and fundraising efforts
  • Monitor financial performance and make strategic adjustments as needed
  • Lead and support fundraising efforts, grant development, and resource acquisition


Leadership Oversight and Accountability

  • Directly supervise and evaluate the Lead School Administrator, Director of Business Operations, and other designated leadership roles
  • Establish clear expectations, goals, and accountability structures for school leadership
  • Monitor execution of key priorities, including instructional leadership, culture, and operations
  • Provide coaching, feedback, and support while ensuring consistent follow through on responsibilities


Instructional and Culture Oversight (Through Leadership)

  • Ensure that strong instructional leadership systems are in place, including:
  • Classroom observation and feedback cycles
  • Data-driven instructional practices
  • Professional development aligned to student needs
  • Ensure a positive, structured, and high-expectations school culture for both students and staff
  • Monitor academic performance and culture data, holding leadership accountable for outcomes


External Relations and Partnerships

  • Serve as the primary external representative of the school
  • Build and maintain relationships with community and business partners, higher education institutions, and external organizations
  • Represent the school in local, regional, and state-level conversations related to education and charter schools
  • Strengthen community trust through clear communication and engagement


Qualifications

  • Bachelor's Degree required, Master’s Degree preferred
  • Significant (10 years) experience in education, nonprofit, or organizational leadership
  • Experience working with or supporting/developing boards and governance structures
  • Strong understanding of school systems, including instruction, culture, and operations
  • Experience with strategic planning, data analysis, and organizational performance management
  • Knowledge of charter schools, public education systems, and regulatory environments preferred
  • Demonstrated ability to lead complex organizations, manage competing priorities, and drive results


Key Skills and Competencies

  • Strategic thinking and execution
  • Strong communication and stakeholder engagement
  • Ability to analyze data and drive decision making
  • Leadership development and performance management
  • Financial and operational oversight
  • Ability to build systems that ensure accountability and follow through
  • Life-long learner focused on continuous organizational improvement


Salary range: $120K - $150K, commensurate with experience


Salary : $120,000 - $150,000

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