Executive Director of Student Success - Colorado Springs School District 11

Colorado Springs School District 11 • Colorado Springs, CO

2d • Onsite

About The Position

The Executive Director of Student Success provides districtwide leadership and strategic oversight for student support systems, including Individualized Education (Gifted, CLDE, Dyslexia, and Special Education), mental health services, behavioral interventions, school discipline, and school nursing. This role ensures equitable access to high-quality instruction, individualized supports, and safe learning environments for all students PK–14. The Executive Director leads strategic planning, implementation, and continuous improvement across all service areas; ensures compliance with federal, state, and local regulations; and advises the Superintendent on complex student matters. The position oversees program effectiveness, policy alignment, budgeting and resource allocation, and supervision of key leaders and staff. Through strong collaboration with school leaders, educators, families, and community partners, the Executive Director promotes aligned systems of support, data-driven decision-making, and inclusive practices that advance student well-being and academic success across the district. All leaders in D11 are expected to: Cultivate safe learning environments where all students and staff feel a sense of belonging and are valued. Lead or support the design and implementation of programs aligned to district and board goals. Use data and evidence to inform continuous improvement and operational effectiveness. Manage personnel, budgets, and resources with efficiency, transparency, and integrity. Build partnerships with schools, families, and community organizations that strengthen outcomes. Model professionalism, ethical leadership, and a commitment to lifelong learning.

Requirements

• Knowledge of: Strategic planning and organizational systems design
• Public sector governance and regulatory compliance
• Program evaluation and performance management
• Budget development and fiscal oversight
• Change management and large-scale implementation
• Skills in: Executive-level leadership and decision-making
• Political acumen and stakeholder management
• Strategic communication and presentation
• Complex problem-solving and risk assessment
• Talent development and performance coaching
• Ability to: Lead large, diverse teams toward measurable results
• Navigate ambiguity and high-stakes environments
• Influence across functions without direct authority
• Balance strategic vision with operational execution
• Maintain composure, discretion, and sound judgment under pressure
• Masters Degree in education, business, public administration or a related field

Nice To Haves

• Preferred qualifications include advanced certification or licensure, experience in K–12 education or government operations, and/or bilingual proficiency (English/Spanish or other district-identified languages).

Responsibilities

• Strategic Leadership & Vision Develop and execute a comprehensive, multi-year strategic plan aligned to district priorities and Board goals.
• Establish and communicate a clear, cohesive vision for student access to high-quality programs, services, and supports across the organization.
• Lead systemic implementation of districtwide frameworks, initiatives, and improvement models to ensure consistency and fidelity.
• Translate regulatory, legislative, and policy changes into actionable strategies and operational plans.
• Champion student-centered practices across all service areas.
• Identify emerging trends, risks, and opportunities; proactively adjust strategy to ensure sustainable impact.
• Organizational & Program Oversight Provide executive oversight of multiple programs, service areas, or operational units within the division.
• Ensure effective development, implementation, and evaluation of programs and services.
• Oversee compliance with applicable federal, state, and local laws, regulations, and district policies.
• Monitor and revise policies, procedures, and operational practices to maintain legal compliance and alignment with district goals.
• Provide executive guidance to the Superintendent and senior leadership on complex, high-impact matters within the division.
• Lead districtwide response efforts or coordinated initiatives that address critical incidents or high-stakes situations, as applicable.
• Supervise, evaluate and provide actionable feedback to directors, managers, and key staff; ensure performance accountability across teams.
• Cross-Functional Collaboration & Stakeholder Engagement Partner with school leaders, central office departments, staff, families, community partners, and external agencies to advance organizational priorities.
• Facilitate strong communication and collaboration among stakeholders to ensure seamless service delivery.
• Promote cross-departmental alignment to reduce silos and strengthen integrated supports.
• Represent the division in Cabinet, Board presentations, community forums, and external partnerships.
• Build and sustain strategic partnerships that enhance services, expand capacity, and strengthen community impact.
• Leadership Development & Organizational Capacity Build leadership capacity within the division through coaching, succession planning, and targeted professional development.
• Provide guidance and technical assistance to administrators and leaders regarding best practices, compliance requirements, and operational expectations.
• Foster a culture of accountability, collaboration, continuous improvement, and high performance.
• Ensure equitable access to professional learning and resources that strengthen organizational effectiveness.
• Data Strategy, Accountability & Continuous Improvement Establish systems to collect, analyze, and report performance data, program effectiveness measures, service utilization metrics, and compliance indicators.
• Use quantitative and qualitative data to inform strategic decision-making and resource allocation.
• Monitor key performance indicators and implement corrective action plans when needed.
• Prepare and present executive-level reports and recommendations to the Superintendent, Board of Education, and stakeholders.
• Lead continuous improvement efforts grounded in measurable outcomes and organizational priorities.
• Financial & Resource Stewardship Develop and oversee complex departmental budgets aligned to strategic goals and performance targets.
• Ensure responsible, transparent, and equitable allocation of resources across programs and operational areas.
• Oversee contracts, vendor relationships, and procurement processes within the division.
• Identify, pursue, and manage external funding opportunities, including grants and partnerships.
• Ensure efficient deployment of personnel, services, and operational supports.
• Governance, Advocacy & Risk Management Advise on and support development of Board policies, administrative regulations, and governance structures.
• Advocate for organizational priorities and the needs of diverse stakeholders at local, state, and national levels.
• Mitigate organizational risk through proactive monitoring, compliance controls, and internal review processes.
• Ensure ethical decision-making, confidentiality, and responsible stewardship of sensitive matters.

Benefits

• Employees in this category will also receive the following for the 2025-2026 school year: Non-Recurring Pay: 8% of base salary in Non-Recurring Pay (distributed as 4% on November paycheck and 4% on May paycheck).
• Professional Development Fund (PDF): __EXEC Pro employees will be allocated $1,500 annually towards a Professional Development Fund (PDF) to be used for professional growth opportunities. Amount allocated will be prorated based upon date and length of hire.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive