Remote Head of Middle School Jobs
Remote Head of Middle School jobs are actively posted by remote-first schools, distributed education organizations, and online learning providers across the country. Employers hiring remotely right now include Connections Education, ACCEL Schools, and Georgia Cyber Academy. Scan the live roles below and apply to whichever ones fit.
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About Oak Education of America LLC
Oak Education of America LLC is a U.S.-registered online school providing 1v1 live English and Math tutoring for K–12 students. We handle student enrollment, scheduling, payment, and parent communication — so our teachers can focus on teaching.
The role
We are hiring part-time ELA teachers for 1v1 live online lessons with students in grades 5–8. Lessons are personalized to each student: reading, writing, and vocabulary, tailored to the student's level and goals.
What you'll do
- Teach 1v1 live online ELA lessons (reading, writing, and vocabulary) to students in grades 5–8
- Prepare lessons using our curriculum and materials, adapted to each student
- Track student progress and share updates with parents
- Work with our team on scheduling and student matching
What we're looking for
- A valid U.S. state teaching certificate (required)
- Currently teaching ELA in a U.S. school (in-service teacher, required)
- Experience teaching middle school ELA (grades 5–8)
- Experience teaching online, or comfortable teaching live online
- Reliable internet connection and a quiet place to teach
Employment type and pay
- Independent contractor (1099), part-time
- Starting at $30/hour
- Flexible schedule — you set your weekly availability; a long-term commitment is expected once we start working together
To apply: Submit your resume via Indeed.
Pay: From $30.00 per hour
Work Location: Remote
About Oak Education of America LLC
Oak Education of America LLC is a U.S.-registered online school providing 1v1 live English and Math tutoring for K–12 students. We handle student enrollment, scheduling, payment, and parent communication — so our teachers can focus on teaching.
The role
We are hiring part-time ELA teachers for 1v1 live online lessons with students in grades 5–8. Lessons are personalized to each student: reading, writing, and vocabulary, tailored to the student's level and goals.
What you'll do
- Teach 1v1 live online ELA lessons (reading, writing, and vocabulary) to students in grades 5–8
- Prepare lessons using our curriculum and materials, adapted to each student
- Track student progress and share updates with parents
- Work with our team on scheduling and student matching
What we're looking for
- A valid U.S. state teaching certificate (required)
- Currently teaching ELA in a U.S. school (in-service teacher, required)
- Experience teaching middle school ELA (grades 5–8)
- Experience teaching online, or comfortable teaching live online
- Reliable internet connection and a quiet place to teach
Employment type and pay
- Independent contractor (1099), part-time
- Starting at $30/hour
- Flexible schedule — you set your weekly availability; a long-term commitment is expected once we start working together
To apply: Submit your resume via Indeed.
Pay: From $30.00 per hour
Work Location: Remote
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Find JobsRemote Head of Middle School Job Market
Who's Hiring
Top Industries Hiring
- Education
- Banking & Financial Services
What Employers Look For
The qualifications that appear most often in remote head of middle school jobs.
- Master's degree in education leadership, administration, or a related field
- Valid state administrator or principal licensure or eligibility to obtain it
- Minimum five to seven years of classroom teaching experience, preferably at the middle school level
- Demonstrated experience supervising and evaluating teachers and instructional staff
- Proficiency with student information systems and data platforms for academic and behavioral tracking
- Experience developing and managing grade-level or divisional curriculum and scheduling
Tips for Your Remote Head of Middle School Job Search
Apply early to remote roles that fit
Migrate Mate lists remote head of middle school openings from across the country in one place. Check it regularly and apply directly to roles that match your credentials and leadership style before postings fill.
Demonstrate async leadership in your application
Remote schools need leaders who can direct faculty and manage curriculum without daily in-person contact. Your cover letter and resume should show specific examples of guiding teams through written communication, video check-ins, and shared digital workflows.
Get fluent with remote education platforms
Virtual schools run on tools like Canvas, Google Classroom, Zoom, and Schoology. Name the platforms you have led on and describe how you used them to manage instruction, track student progress, or coordinate staff across locations.
Prepare for a multi-round video interview process
Remote schools often run two or three video interview rounds, sometimes including a leadership scenario or a live demonstration of how you would handle a faculty or curriculum challenge. Practice speaking clearly and concisely on camera before your first round.
Remote Head of Middle School Jobs: Frequently Asked Questions
How do I get a remote head of middle school job?
Target online schools, virtual charter networks, and distributed curriculum organizations, since those are the employers most likely to hire a head of middle school remotely. Remote hiring panels screen heavily for async communication, the ability to manage faculty and curriculum without in-person oversight, and comfort with video-based leadership. Candidates who can show documented outcomes from previous leadership roles, strong written communication, and experience with learning management systems stand out most.
Which companies hire remote head of middle schools?
Companies hiring remote head of middle schools right now include Connections Education, ACCEL Schools, and Georgia Cyber Academy, based on current remote listings on Migrate Mate as of November 2026. These tend to be online schools, virtual academies, and distributed education nonprofits that operate fully remote or across multiple locations.
Can you get a remote head of middle school job with no experience?
Yes, but remote entry-level head of middle school roles are limited because employers expect you to operate independently from day one without on-site mentorship. The most accessible entry paths are virtual teaching roles that lead to remote department lead positions, or coordinator roles at online schools. Demonstrating strong async communication, curriculum project ownership, and self-directed professional development can open doors when formal leadership experience is thin.
Do you need a degree for remote head of middle school jobs?
Usually, yes. Most remote head of middle school roles require at least a bachelor's degree, and many expect a master's in education leadership or a related field, plus a valid administrative credential. That said, remote employers also weigh demonstrated leadership results, curriculum development work, and measurable student outcome improvements alongside formal credentials.
Which industries hire the most remote head of middle schools?
Remote head of middle school roles concentrate in Education and Banking & Financial Services, based on current remote listings on Migrate Mate as of November 2026. These sectors rely on distributed teams managing instruction and operations across multiple states or time zones, which makes remote school leadership a practical fit.
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