Online Instructional Specialist (High School & Middle School)

Williamsburg Learning

1d•Remote

About The Position

Williamsburg Learning is hiring one full-time Middle School Instructional Specialist and one full-time High School Instructional Specialist to support mentors in improving classroom instruction and student achievement through collaboration, coaching, and professional development. These roles will work closely with educators to analyze data, implement effective teaching strategies, and integrate curriculum standards and technology into daily instruction. The instructional specialists will model best practices, provide mentor feedback, and help mentors create engaging learning environments that meet students’ diverse needs. Their goal is to build mentor capacity and promote continuous improvement across Williamsburg Learning.

Requirements

Bachelor's degree in Education, Instructional Design, or a related field.
Minimum 3 years of classroom teaching experience, with demonstrated results in student engagement and achievement.
Experience coaching, mentoring, or leading other educators.
Proficiency with Canvas LMS, Zoom, and data analysis tools.
Strong written and verbal communication skills.
Ability to work effectively across diverse learner populations, including students with IEPs, 504 plans, ELL, and MTSS support needs.
Strong organizational and problem-solving skills with the ability to manage multiple priorities simultaneously.
Alignment with Williamsburg Learning's Socratic liberal arts educational philosophy and mission.
Student-centered approach with a deep commitment to student voice and Socratic discussion.
Ability to build trust and rapport with mentors at all experience levels.
Strong attention to detail and accuracy in coaching documentation and data tracking.
Collaborative team player who can also work independently and take initiative.
Flexibility and adaptability in a fast-paced, fully remote environment.
Growth mindset and proactive approach to continuous improvement.
Comfort with data — ability to read, interpret, and coach from Zoom analytics and student performance data.
Deep belief that instructional quality is a system problem, not a people problem.

Nice To Haves

Master's degree in Education, Instructional Coaching, Curriculum & Instruction, or a related field.
Prior experience in an online or asynchronous learning environment.
Familiarity with learning science research (Bjork, Hattie, Yeager) and its application to instructional coaching.
Experience facilitating professional development or adult learning.
Familiarity with Zoom analytics, talk-time data, or similar instructional data systems.
Experience with Trainual, Socratic discussion facilitation, or inquiry-based instructional models.

Responsibilities

Support new and seasoned mentors through structured Coaching Cycles aligned to the WL Cycles framework.
Track new mentor onboarding progress through the 4 to 6-week structured sequence, maintaining documentation of milestones, goals, and data checkpoints.
Work with mentors who need additional support — new and experienced — to identify areas for growth, set instructional goals, and provide targeted coaching through completion.
Conduct regular class observations using the WL Student Success Rubric as the observational lens; provide structured pre- and post-observation coaching conversations.
Maintain accurate coaching logs and progress documentation for each assigned mentor cohort.
Stay current on effective teaching methods, technologies, and learning science (Bjork, Hattie, Yeager); translate research into actionable coaching for mentors.
Coach mentors in strategies that increase student talk time with a particular focus on Socratic questioning, discussion facilitation, and the Genuine Question framework.
Introduce and support the integration of AI tools that strengthen — rather than replace — mentor instructional judgment.
Model instructional best practices in live sessions, co-teaching opportunities, and PD facilitation.
Support the implementation and ongoing use of the Socratic Method across assigned mentor cohorts.
Design and present targeted professional development sessions for the Friday PD block, grounded in current inquiry cycle data, Zoom analytics, and mentor needs.
Build PD session agendas, materials, and artifacts that produce measurable change.
Facilitate WL Cycle Kickoff Fridays and Implementation Fridays (evidence share, mid-cycle adjustments, co-planning) for assigned mentor cohorts.
Collaborate with the Director of Instruction & Assessment to align PD design with the Student Success Rubric and the Six Mentor Practices framework.
Act as a thought partner to mentors in identifying student success indicators, designing evidence of learning, and analyzing Zoom talk-time data to drive instructional decisions.
Work with mentors to develop better assessments, interpret student performance data, and adjust teaching practice accordingly — based on evidence, not intuition.
Generate and maintain per-student accommodation summaries (IEP, 504, ELL, MTSS) for assigned mentor cohort; ensure mentors are briefed before each session.
Ensure pre-class scaffolds are deployed for students with support plans.
Monitor whether accommodation plans are being implemented with fidelity; flag concerns to the Director of Instruction & Assessment.
Stay current on special education compliance requirements for assigned grade span (MS or HS) and maintain documentation in accordance with WL policy.