Chief of Schools

Chief of School -- Escuela Popular

Reports to: Executive Director

Launch a Future of Systems & Strategy at a School That Roots for Its Community

At Escuela Popular, we cultivate the next generation of critical thinkers, problem-solvers, and innovators. Founded over 40 years ago as a grassroots community school, we have grown into a vibrant, culturally-rich, multi-generational learning community in East San Jose. Our unique, family-focused dual-language model celebrates bilingualism as a superpower, creating an educational environment where student and adult learner identity is honored, and holistic success thrives.

Do you love turning vision into seamless execution? We are seeking a strategic Chief of Staff to serve as the organizational linchpin and a true force-multiplier for our leadership. Here, we champion systems that empower, foster cross-team collaboration, and believe that operational excellence is the foundation for transformative educational impact.

What You'll Do

Strategic Leadership & Organizational Alignment

• Serve as the strategic right hand and thought partner to the Executive Director, translating big-picture goals into clear, actionable plans.
• Lead the Executive Leadership Team, ensuring strong coordination, shared accountability, and cohesive direction.
• Drive data-informed progress monitoring of key initiatives and steer annual strategic planning processes.

Cross-Departmental Coordination & Systems Building

• Architect and maintain high-quality internal systems for schoolwide project management, communication, and operational consistency.
• Identify opportunities for improvement and lead change management to enhance efficiency and impact across all departments.
• Ensure powerful alignment between Academics, Operations, Student Services, and Adult Education to support whole-school outcomes.

Leadership Development & Team Support

• Provide coaching, guidance, and accountability to Directors and Managers, modeling emotionally intelligent leadership.
• Lead professional learning and culture-building initiatives for leadership teams, including retreats and management training.
• Support talent development strategies in collaboration with HR and departmental leaders.

Communication, Culture, & Stakeholder Engagement

• Strengthen internal communication structures that promote transparency, cohesion, and shared ownership of our mission.
• Reinforce Escuela Popular’s values and dual-language focus through every system and staff interaction.
• Act as a key liaison for the Executive Director and support board preparation, reporting, and stakeholder engagement.

Operational Excellence & Special Projects

• Oversee the execution of cross-functional initiatives and special projects, ensuring on-time, high-quality implementation.
• Partner with Operations to ensure compliance with all charter, local, state, and federal requirements.
• Lead organizational readiness for visits, audits, and continuous improvement cycles.

You Must Have:

• Significant experience in a senior leadership role, preferably in education, nonprofit management, or public service.
• A proven track record of managing leaders and cross-functional teams to success.
• Demonstrated expertise in building high-quality operational systems and processes.
• Exceptional strategic thinking, organizational, and relational abilities.

You'll Be a Perfect Fit If You:

• Possess knowledge of K-12 and/or adult education landscapes.
• Hold bilingual fluency in English and Spanish, honoring our community's linguistic assets.
• Skillfully hold teams accountable while fostering trust, psychological safety, and collaboration.
• Navigate multiple priorities and lead through ambiguity with resilience and a solutions-orientation.
• Lead with deep cultural humility, emotional intelligence, and an unwavering commitment to educational equity.
• Are a continuous improvement champion who believes strong systems enable human potential.

Why You'll Love Leading Here

At Escuela Popular, we believe that transformative leadership starts with strategic support and authentic community. You will thrive at the heart of a mission-driven team, working to strengthen the systems that directly empower youth, adult learners, and families. If you’re looking for a leadership role where your operational expertise fuels social justice and community empowerment, this is the place to make a lasting impact.

We Support You & Your Family:

• Comprehensive Benefits: Medical, dental, vision, and life insurance.
• Financial Wellbeing: Competitive salary commensurate with experience.
• Time to Recharge: Generous paid time off and sick leave.

We Foster Your Growth:

• Strategic Impact: Directly shape the operational backbone of a unique, multi-generational educational model.
• Continuous Learning: Engage in ongoing professional development and strategic thought partnership at the highest level.
• A True Team: Join a cohesive, passionate leadership community where your strategic mind is valued and your contributions are essential to our mission.

Ready to Join Us?

If you are ready to operationalize a powerful mission and become the strategic engine for a school that feels like family, we encourage you to apply.