Chief of Staff

Jubilee Academies•San Antonio, TX

1d•Onsite

About The Position

The Chief of Staff to the Superintendent serves as a strategic advisor, executive partner, and organizational integrator for Jubilee Academies. The role advances the Superintendent’s priorities, strengthens organizational alignment, and ensures effective execution and follow-through across the organization. It 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 Chief of Staff works across departments and regions to remove barriers, strengthen collaboration, monitor progress toward district priorities, and translate commitments into measurable results. The position coordinates strategic projects, executive decision-making and follow-through, staffing and workforce planning, enrollment and family engagement strategy, and external relationships as assigned. It reports to the Superintendent and is an at-will, senior leadership/executive position based at the Jubilee Academies District Office in San Antonio, Texas. The position is listed as 223 workdays, with occasional extended or irregular hours and travel across regions, campuses, and external convenings.

Requirements

At least 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.
Proven success leading complex projects, facilitating work across multiple departments or regions, using data to drive decisions, and moving organizational priorities from planning to execution.
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.
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 priorities into clear action, ownership, and measurable outcomes.
Understanding of how to align people, systems, resources, and communication across multiple departments and regions.
Exceptional judgment, discretion, emotional intelligence, and ability to handle confidential or sensitive information.
Excellent executive written and verbal communication skills.
Strong strategic planning, problem-solving, systems-thinking, organizational leadership, facilitation, project management, and change-management abilities.
Ability to influence and drive execution across functions without relying solely on formal supervisory authority.
Ability to establish accountability systems and ensure consistent organizational follow-through.
Ability to analyze organizational data and translate findings into clear recommendations and executive decisions.
Proficiency with student data and enrollment platforms such as SchoolMint and Ascender; 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.
Ability to maintain emotional control, sound judgment, and strategic focus under pressure and manage multiple high-priority initiatives and competing deadlines.
Frequent standing, walking, and light lifting; travel across regions, campuses, and external convenings is required.
Occasional prolonged and irregular work hours, including evenings and weekends, for meetings, events, emergencies, or district needs.

Nice To Haves

Preferred experience in Human Resources, Talent Management, organizational design, workforce strategy, staffing allocation, or personnel planning.
Knowledge of talent strategy, leadership development, succession planning, coaching, and approaches for building leader and team capacity.

Responsibilities

Serve as a trusted advisor to the Superintendent and translate organizational vision and priorities into strategies, actions, responsibilities, and measurable outcomes.
Track the Superintendent’s priority initiatives, decisions, commitments, timelines, and next steps to ensure follow-through.
Develop and maintain executive accountability systems, dashboards, trackers, and routines for monitoring priorities, performance indicators, risks, and implementation progress.
Coordinate Cabinet action items and cross-functional commitments; identify stalled work and elevate unresolved barriers to the Superintendent.
Support planning and effectiveness of Cabinet meetings, executive leadership meetings, strategic planning sessions, and other Superintendent-led convenings.
Coordinate executive presentations, board materials, strategic recommendations, policy-related information, and executive summaries with responsible department leaders.
Maintain records of major organizational decisions, ownership, deadlines, and required follow-through.
Connect central office departments, regional leadership, and campuses to strengthen communication, coordination, and execution.
Convene and facilitate teams working on districtwide priorities that require collaboration across departments or regions.
Identify organizational and operational barriers, work with leaders to develop solutions, and escalate unresolved issues when needed.
Evaluate district processes and facilitate workflow improvements that strengthen organizational effectiveness.
Support planning, communication, and implementation of major organizational changes and strategic initiatives.
Lead high-priority initiatives and special projects assigned by the Superintendent; establish project plans, milestones, ownership, timelines, and success measures.
Monitor initiative implementation and provide timely updates on progress, risks, barriers, and decisions needed.
Coordinate districtwide initiatives while ensuring functional ownership remains with the appropriate leaders.
Support crisis and emergency coordination at the Superintendent’s direction in partnership with Operations, Communications, Human Resources, campus leadership, and other departments.
Coordinate review of staffing ratios, staffing models, vacancies, and personnel allocations.
Facilitate staffing and headcount planning with department and regional leaders, principals, Finance, and Human Resources.
Support evaluation of organizational structures, staffing capacity, departmental needs, and leadership allocations.
Monitor personnel metrics, including vacancies, turnover, staffing ratios, and workforce trends, and make relevant information available for executive decisions.
Partner with Human Resources and Talent leadership to align workforce planning and talent strategies with district priorities, while HR retains ownership of compliance, employee relations, personnel processes, and talent operations.
Coordinate districtwide strategic planning for enrollment growth, student recruitment, retention, and family engagement.
Monitor enrollment trends, recruitment pipelines, conversion data, retention patterns, and progress toward enrollment targets.
Facilitate enrollment and family-engagement collaboration among Communications, Marketing, Operations, regional leaders, campuses, and other responsible departments.
Partner with Communications and Marketing leadership to align outreach strategies with enrollment goals and organizational priorities.
Analyze student retention trends and work with regional and campus leaders to identify ways to strengthen family engagement and student persistence.
Identify districtwide enrollment or retention barriers and elevate unresolved issues to the Superintendent.
Establish and maintain systems that support effective operation of the Superintendent’s Office and coordinate executive priorities, deadlines, deliverables, and leadership commitments.
Ensure information requiring Superintendent review or decision is organized, concise, timely, and supported by appropriate data or recommendations.
Coordinate executive leaders when Superintendent decisions require cross-department implementation and maintain confidentiality in handling sensitive matters.
Serve as a strategic liaison between Jubilee Academies and the Jubilee Foundation when assigned by the Superintendent.
Represent the Superintendent or Jubilee Academies at community functions, authorizer meetings, partner convenings, and other external engagements when requested.
Support strategic partnerships that advance the organization’s mission, growth, student success, and community presence.
Coordinate external engagement with Communications and other responsible leaders to align it with district messaging and priorities.
Promote Jubilee Academies’ mission, vision, core values, strategic priorities, accountability, collaboration, responsiveness, and continuous improvement.
Build professional relationships with students, families, staff, campus and district leaders, and community partners; represent Jubilee Academies professionally and exercise sound judgment.
Foster a positive, collaborative, accountable, results-driven, equitable, fair, consistent, and inclusive culture across departments, regions, and campuses.