Assistant Executive Director - Middle & High School (Remote - CO Based ONLY)

About Williamsburg Learning of Colorado

Williamsburg Academy of Colorado (WAC) is a tuition-free, full-time online public school serving students in grades 6–12 across the state. As part of Williamsburg Learning, we are committed to preparing promising students for meaningful lives as principled leaders through transformational learning experiences that spark curiosity, growth, and purpose.

At WAC, learning is both rigorous and flexible. Our model blends independent learning with live mentor support, empowering students to take ownership of their education while being deeply known, challenged, and supported. We focus on developing the whole student—academically, personally, and socially—through strong relationships, engaging content, and a vibrant community.

Across Williamsburg Learning, we live by our core values—Growth, Right Action, and a Culture of Belonging—and believe work should be meaningful and energizing. Our team is authentic, collaborative, and committed to doing what is best for students and for one another.

We also invest in our people, offering 100% paid health premiums for full-time employees (75% for families), a 100% 401(k) match up to 4%, PTO, and additional benefits that support well-being and growth. If our mission and culture resonate with you, we would love to have you on our team.

Position Summary

The Assistant Executive Director serves as a key leader within Williamsburg Academy of Colorado (WAC), partnering closely with the Executive Director to ensure operational excellence, a thriving culture of belonging, and strong alignment with state and BOCES requirements. This role is a leadership development position with increasing responsibility across all aspects of school leadership, designed to grow in scope and responsibility over time and to offer opportunities for expanded leadership based on performance and organizational needs.

Essential Duties (Top 5 Roles)

1) Lead, Manage, and Hold Accountable (LMA)

• Lead and manage WAC team members through weekly L10 meetings and structured communication rhythms
• Conduct quarterly conversations and support annual performance reviews
• Provide coaching, feedback, and accountability aligned with WL core values
• Identify and develop emerging leaders within the organization
• Partner with the Executive Director and People Operations to support hiring, onboarding, and team development

2) Cultivate a Vibrant School Culture & Community Experience

• Ensure a “first-class” experience for students, families, and team members
• Lead initiatives that foster belonging, connection, and engagement across the WAC community
• Oversee communication rhythms with families and stakeholders
• Collaborate with WL Academic leadership to support student engagement and leadership development opportunities
• Continuously improve the overall student and family experience

3) Oversee Compliance, Student Support, and BOCES Alignment

• Ensure compliance with WAC’s MDOA and all Education reEnvisioned BOCES requirements
• Lead preparation and execution of BOCES site visits, including evidence collection and coordination
• Oversee student support systems, including Special Education (IEPs), 504 accommodations, MTSS frameworks, Gifted & Talented (ALPs), Multilingual Learners (ELD Plans), and Health Care Plans
• Monitor regulatory requirements and proactively address compliance risks
• Partner with the Executive Director to ensure alignment with state and accreditation expectations

4) Support Academic Oversight and Performance

• Develop a deep understanding of Williamsburg Learning’s academic model and implementation within WAC
• Monitor student academic performance data and support intervention strategies
• Collaborate with the WL Director of Academics to ensure alignment and quality of program delivery
• Support mentors in maintaining high standards of student engagement and learning outcomes
• Gradually take on increased responsibility in academic oversight as competency develops

5) Operational Leadership & Strategic Execution

• Partner with the Executive Director to execute school-wide priorities and initiatives
• Own key operational systems and ensure consistency and follow-through across the organization
• Identify opportunities for improvement in systems, processes, and communication
• Support budget awareness and operational decision-making
• Step into leadership responsibilities in the absence of the Executive Director when needed

Non-Essential Duties

Please note that this job description is not designed to cover or contain a comprehensive listing of the activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time, with or without notice.

Minimum Qualifications

• Resides in Colorado
• Holds a valid Colorado Principal License or is actively eligible and committed to obtaining licensure within 12 months of hire
• Strong leadership and people management experience
• Ability to lead through influence, coaching, and accountability
• High level of organizational awareness and operational thinking
• Experience in education, EdTech, or related field preferred
• Strong communication and relationship-building skills
• Alignment with classical education philosophy and leadership development
• Ability to manage multiple priorities in a dynamic environment

Physical Requirements & Working Conditions

• Full-time, year-round position
• Primarily remote with occasional travel as needed
• Ability to manage a fast-paced, evolving environment

Benefits

After meeting the eligibility requirements, benefits are available, including Health, 401(k) Retirement, Paid Holidays, and Paid Time Off.

Salary Range

• $80,000 - $90,000 annual salary

Williamsburg Learning is an Equal Opportunity Employer