Chief of Staff

Position Hours: 223 workdays, occasional extended hours for board meetings, emergencies, and events Length of Term/Employment: 223 workdays / At-Will Reports to: Superintendent Position Type: Senior Leadership / Executive Position Mission The Chief of Staff to the Superintendent serves as a strategic advisor, executive partner, and organizational integrator to the Superintendent.

The position is responsible for advancing the Superintendent's priorities, strengthening organizational alignment, and ensuring effective execution and follow-through across Jubilee Academies. The Chief of Staff leads and coordinates high-priority strategic initiatives, executive office operations, cross-functional accountability systems, workforce and staffing planning, and other strategic portfolios assigned by the Superintendent.

The position works across departments and regions to remove barriers, strengthen collaboration, monitor progress toward district priorities, and ensure commitments are translated into measurable results. Position Minimum Qualifications Experience Minimum of 7 years of progressive leadership experience in charter school networks, school district central offices, nonprofit organizations, or similarly complex organizations.

Demonstrated senior-level leadership experience managing organizational priorities, cross-functional initiatives, strategic planning, or executive operations. Preferred experience in Human Resources, Talent Management, organizational design, workforce strategy, staffing allocation, or personnel planning. Proven success leading complex projects, facilitating work across multiple departments or regions, using data to drive decisions, and ensuring organizational priorities move from planning to execution.

Knowledge Deep understanding of charter school governance, multi-regional school operations, organizational leadership, workforce planning, staffing allocation models, and enterprise-level strategic planning. Strong knowledge of organizational change management, including leading teams through growth, transition, restructuring, and implementation of new systems, priorities, and ways of working.

Knowledge of talent strategy, leadership development, succession planning, coaching, and approaches for building the capacity of leaders and teams to drive sustained organizational performance. Strong understanding of student enrollment and recruitment systems, organizational performance management, operational systems, and cross-functional execution.

Knowledge of executive decision-making, board and stakeholder relations, systems-level accountability, and translating organizational priorities into clear action, ownership, and measurable outcomes. Understanding of how to align people, systems, resources, and communication across multiple departments and regions to support organizational effectiveness and continuous improvement.

Job Duties/Responsibilities

1. Strategic Advisory & Executive Office Leadership Strategic Advisor: Serve as a trusted advisor to the Superintendent, helping translate organizational vision and priorities into clear strategies, actions, responsibilities, and measurable outcomes. Superintendent Priority Management: Maintain visibility into the Superintendent's highest-priority initiatives and ensure that commitments, decisions, timelines, and next steps are documented, monitored, and completed. Executive Accountability: Develop and maintain systems, dashboards, trackers, and executive routines that provide visibility into districtwide priorities, performance indicators, risks, and implementation progress. Cabinet Follow-Through: Coordinate Cabinet action items and cross-functional commitments, identify stalled or delayed work, and elevate unresolved barriers to the Superintendent when necessary. Executive Meeting Leadership: Support the planning and effectiveness of Cabinet meetings, executive leadership meetings, strategic planning sessions, and other Superintendent-led convenings. Board & Executive Support: Coordinate the preparation and alignment of executive presentations, board materials, strategic recommendations, policy-related information, and executive summaries in collaboration with responsible department leaders. Decision Tracking: Maintain systems that document major organizational decisions, ownership, deadlines, and required follow-through.
2. Cross-Functional Alignment & Organizational Execution Organizational Integration: Serve as a primary connector across central office departments, regional leadership, and campuses to strengthen communication, coordination, and execution. Cross-Functional Leadership: Convene and facilitate teams around districtwide priorities that require collaboration across multiple departments or regions. Barrier Removal: Identify operational or organizational barriers affecting implementation and work with the appropriate leaders to develop solutions. Escalation & Accountability: Monitor unresolved cross-functional issues and elevate concerns to the Superintendent when established collaboration and accountability structures have not resulted in resolution. Workflow Optimization: Continuously evaluate district processes, identify inefficiencies, and facilitate improvements that strengthen organizational effectiveness. Change Management: Support the planning, communication, and implementation of major organizational changes and strategic initiatives.
3. Strategic Initiative & Special Project Management Lead high-priority initiatives and special projects assigned by the Superintendent. Develop clear project plans, milestones, ownership structures, timelines, and success measures for major initiatives. Monitor implementation and provide the Superintendent with timely updates regarding progress, risks, barriers, and decisions needed. Coordinate districtwide initiatives that require contributions from multiple departments while ensuring ownership remains with the appropriate functional leaders. Support crisis and emergency coordination at the direction of the Superintendent and in partnership with Operations, Communications, Human Resources, campus leadership, and other responsible departments.
4. Staffing, Workforce Planning & Organizational Design Staffing Model Monitoring: Coordinate districtwide review of staffing ratios, staffing models, vacancies, and personnel allocations to support operational efficiency, instructional priorities, and financial sustainability. Staffing Planning: Facilitate staffing and headcount planning conversations with department leaders, regional leaders, principals, Finance, and Human Resources. Organizational Planning: Support the Superintendent in evaluating organizational structures, staffing capacity, departmental needs, and leadership allocations. Workforce Analytics: Monitor key personnel metrics, including vacancies, turnover, staffing ratios, and workforce trends, and ensure relevant information is available for executive decision-making. HR & Talent Partnership: Partner with Human Resources and Talent leadership to align workforce planning and talent strategies with district priorities while maintaining Human Resources ownership of HR compliance, employee relations, personnel processes, and talent operations.
5. Enrollment, Growth & Family Engagement Strategy Enrollment Strategy: Coordinate districtwide strategic planning related to enrollment growth, student recruitment, retention, and family engagement. Enrollment Performance Monitoring: Monitor enrollment trends, recruitment pipelines, conversion data, retention patterns, and progress toward districtwide enrollment targets. Cross-Functional Coordination: Facilitate collaboration among Communications, Marketing, Operations, regional leaders, campuses, and other departments responsible for enrollment and family engagement. Marketing Alignment: Partner with Communications and Marketing leadership to ensure outreach strategies align with district enrollment goals and organizational priorities. Family Retention: Analyze student retention trends and work with regional and campus leaders to identify opportunities to strengthen family engagement and student persistence. Escalation: Identify districtwide barriers affecting enrollment or retention and elevate unresolved issues to the Superintendent for action.
6. Superintendent Office Operations Establish and maintain systems that support effective operation of the Superintendent's Office. Coordinate executive priorities, organizational deadlines, strategic deliverables, and major leadership commitments. Ensure information requiring Superintendent review or decision is organized, concise, timely, and supported by appropriate data or recommendations. Support coordination among executive leaders when Superintendent decisions require cross-department implementation. Maintain confidentiality and sound judgment when handling sensitive executive, personnel, operational, or organizational matters.
7. Foundation, Community & External Relations Serve as a strategic liaison between Jubilee Academies and the Jubilee Foundation as assigned by the Superintendent to support organizational alignment, community partnerships, and external resources. Represent the Superintendent or Jubilee Academies at community functions, authorizer meetings, partner convenings, and other external engagements when requested. Support strategic partnerships that advance Jubilee Academies' mission, growth, student success, and community presence. Coordinate with Communications and other responsible leaders to ensure external engagement is aligned with district messaging and priorities. Special Knowledge / Skills Exceptional judgment, discretion, emotional intelligence, and ability to manage confidential or sensitive information. Excellent executive written and verbal communication skills. Strong strategic planning, problem-solving, systems-thinking, and organizational leadership abilities. Ability to influence and drive execution across functions without relying solely on formal supervisory authority. Demonstrated ability to establish accountability systems and ensure consistent organizational follow-through. Strong facilitation, project management, and change-management skills. Ability to analyze organizational data and translate findings into clear recommendations and executive decisions. Proficiency with student data and enrollment platforms, such as School. Mint and Ascender, and familiarity with dashboards, project management tools, and organizational performance systems. Ability to prioritize competing demands and maintain strategic focus in a fast-paced executive environment. Charter & Community Responsibilities Promote and uphold the mission, vision, core values, and strategic priorities of Jubilee Academies. Build strong professional relationships with students, families, staff, campus leaders, district leaders, and community partners. Support a culture of accountability, collaboration, responsiveness, and continuous improvement. Represent Jubilee Academies and the Superintendent professionally in all internal and external engagements. Maintain confidentiality and exercise sound professional judgment at all times. Charter Atmosphere Foster a positive, collaborative, accountable, and results-driven culture aligned with Jubilee Academies' mission. Promote clear communication, shared ownership, and professional collaboration across departments and regions. Communicate respectfully, transparently, and professionally with internal and external stakeholders. Promote equity, fairness, consistency, and inclusion across all regions and campuses. Model a solutions-oriented mindset and a strong commitment to organizational excellence. Working Conditions Mental Demands / Physical Demands / Environmental Factors: Maintain emotional control, sound judgment, and strategic focus under pressure. Manage multiple high-priority initiatives and competing deadlines. Occasional prolonged and irregular work hours, including evenings and weekends for meetings, events, emergencies, or district needs. Frequent standing, walking, and light lifting. Travel required across regions, campuses, and external convenings. The foregoing statements describe the general purpose and responsibilities assigned to this job and are not an exhaustive list of all responsibilities and duties that may be assigned or skills that may be required.