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Location: Remote (Ohio) with frequent travel throughout the region.

Schedule: Full-Time | 40 hours/week | 10-Month School Year

Supervises: 10–12 Graduation Coaches

Start Date: July 31, 2026

Salary: Starting from $65,000 – $75,000/year + benefits

Reimagine school. Support students. Change lives. At ChallengeU, we do high school differently! We’re a fully online dropout recovery and prevention high school, dedicated to helping students aged 14–21 who have fallen behind or disconnected from traditional education. Through flexibility, compassion, and personalized support, we help students reclaim their path to graduation.

Note: While this is primarily a remote position, it requires frequent travel throughout the state of Ohio to support coaching oversight, student engagement, and program success.

What You'll Do:

As a Lead Graduation Coach serves as a bridge between the coaching team and leadership, helping ensure that coaches are supported, accountable, and equipped to effectively engage students.Your role will include:

  • Team Leader: Hold weekly meetings with your assigned team of 10–12 Graduation Coaches to provide guidance, share updates, and ensure alignment with program goals.
  • Performance Monitor: Track coach performance, engagement metrics, and documentation compliance to ensure students are receiving consistent and effective support.
  • Coach Mentor: Support coaches in developing strategies for student engagement, intervention planning, and overcoming barriers to student success.
  • Intervention Strategist: Assist coaches with complex student situations by helping develop improvement plans, intervention strategies, and graduation tracking support.
  • Student Success Coach: Maintain and manage a personal caseload of students, providing direct coaching and support to help them stay engaged and on track to graduate.
  • Data Champion: Review key performance indicators such as weekly engagement benchmarks, offline time completion, and use of communication tools to monitor program effectiveness.
  • Documentation Guardian: Ensure consistent completion of coach tasks including communication logs, engagement tracking, truancy monitoring and offline time grading.
  • Trend Analyzer: Monitor communication patterns and engagement data to identify trends, challenges, and opportunities to strengthen coaching practices.
  • Leadership Liaison: Serve as the primary communication bridge between assigned coaches and the Director of Engagement, sharing updates, concerns, and progress.
  • Traveling Support Partner: Travel throughout Ohio to support coaches, strengthen student engagement, and assist with program initiatives when needed.

Who You Are:

  • A strong leader who enjoys mentoring and supporting other staff
  • Experienced working in fully online education environments supporting students remotely.
  • Passionate about supporting at risk students ages 14–21 and helping them overcome barriers to graduation.
  • A collaborative communicator who can connect with both students and staff
  • Organized, adaptable, and comfortable managing multiple responsibilities.
  • Emotionally intelligent with strong communication and motivational skills.
  • Comfortable analyzing data and using metrics to help guide decision making.

What You'll Need:

  • Bachelor’s degree in social work, counseling, education, or a related field required.
  • 5 + years of experience working in a fully online education environment (virtual high school, online mentoring/tutoring, tele-counseling, etc.)
  • 5 + years supporting at-risk high school students (grades 9–12) in roles such as counselor, teacher, social worker, or behavioral specialist
  • Experience working with at-risk youth ages 14-21.
  • Demonstrated leadership, mentoring, or team supervision experience.
  • Strong technology skills and experience with tools such as Google Workspace, Microsoft Office, learning management systems, and digital communication platforms
  • Strong organizational, documentation, and data monitoring skills
  • Valid driver’s license and reliable transportation for frequent travel
  • Reliable high-speed internet for remote work
  • Ability and willingness to travel frequently throughout Ohio.

Why Work With Us?

At ChallengeU, we do more than check boxes — we reignite potential! Join a caring, creative team that believes in second chances. We offer a flexible, mission-driven work environment where your impact is felt every day.

Benefits:

  • Health, Dental & Vision Insurance
  • Paid Time Off
  • Flexible schedule + Remote-first work
  • State Retirement
  • Professional development support

Ready to help students believe in school again — and in themselves? Apply now and bring your experience, empathy, and virtual know-how to a team that’s changing lives every day!

Pay: $65,000.00 - $75,000.00 per year

Benefits:

  • Dental insurance
  • Flexible schedule
  • Health insurance
  • Paid time off
  • Professional development assistance
  • Retirement plan
  • Vision insurance

Application Question(s):

  • Willing and able to meet with students throughout the state of Ohio for testing and engagement/ relationship building.

Education:

  • Bachelor's (Required)

Experience:

  • supporting at-risk high school students: 5 years (Preferred)
  • working in a fully online education environment: 5 years (Preferred)

Location:

  • Ohio (Required)

Willingness to travel:

  • 50% (Required)

Work Location: Remote

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