ChallengeU, Chief Schools Officer

ABOUT CHALLENGEU

ChallengeU is a Canadian B-Corp operating virtual schools that serve dropout recovery students. Our mission is to ensure every student has a bright future, regardless of their circumstances. We combine personalized coaching with innovative technology to re-engage students who have disconnected from traditional education.

In Quebec, we serve 10,000+ students annually through partnerships with school districts, establishing ourselves as the market leader in dropout recovery education. Our Ohio Community School launched in 2023 and has grown from 250 students to 1,200+ students, consistently meeting or exceeding state graduation standards.

Ohio represents our blueprint for U.S. expansion. Unlike Quebec where we partner with districts, in Ohio we operate our own school with full control over educational services. This creates an unprecedented opportunity to innovate, iterate rapidly, and build scalable systems that will transform dropout recovery education nationally.

To learn more about ChallengeU, please visit www.challengeu.com.

THE OPPORTUNITY

We are seeking a Chief Schools Officer to lead ChallengeU Ohio through its next phase of growth: scaling from 1,200 to 7,500+ students while maintaining quality outcomes and building systems that can be replicated across multiple states.

This is not a traditional superintendent role. You will be building the operational infrastructure, leadership team, and processes required to serve vulnerable students at unprecedented scale. You will pioneer AI-enhanced coaching tools, establish proof points for national expansion, and potentially impact over 100,000 students in the next decade.

The right candidate will inherit a proven model, a committed team, and the backing of an organization that has successfully scaled similar operations in Canada. What we need is a leader who can systematize what works, build organizational capacity, and maintain relentless focus on student outcomes as we grow.

KEY RESPONSIBILITIES

Strategic Leadership

• Own the execution of Ohio's growth strategy: 2,000 students (Year 1), 4,000+ students (Year 2), 7,500+ students (Year 3);
• Develop and manage annual operating budgets with accountability for financial performance;
• Build the organizational blueprint for multi-state expansion and lead efforts to secure licensure in additional states.
• Partner with Quebec leadership on shared services (HR, Finance, Technology, Marketing).

Operational Excellence

• Ensure full compliance with Ohio Department of Education requirements;
• Oversee all school operations: enrollment, student services, academics, testing, records;
• Implement data-driven decision making across all departments;
• Manage vendor relationships and service provider contracts;
• Build scalable processes that maintain quality as enrollment grows.

Team Leadership

• Scale the Ohio team from 60 to 100+ employees in Year 1;
• Evaluate, develop, and optimize leadership structure as needed;
• Build a culture of accountability, continuous improvement, and student-centered service;
• Implement rigorous performance management and professional development;

Innovation & Technology

• Partner with Product team to define requirements for coaching tools and student engagement platforms;
• Support deployment of AI-enhanced coaching tools (Pilot project in Year 1);
• Drive adoption of technology solutions across the organization and identify opportunities for automation and efficiency gains.

Requirements

REQUIRED QUALIFICATIONS

• Ohio Superintendent License (or ability to obtain before start date);
• 5+ years of school or district leadership experience;
• Virtual/online school leadership experience;
• Charter school or community school experience;
• Familiarity with ed-tech tools and/or AI applications in education;
• Demonstrated experience scaling educational operations (ideally from 1,000 to 5,000+ students);
• Strong financial acumen: budget development, P&L management, resource allocation;
• Track record of building and developing high-performing teams;
• Data-driven approach to decision making and performance management;
• Experience with state compliance, accountability systems, funding and report cards.

PREFERRED QUALIFICATIONS

• Experience opening schools in multiple states;
• Background in grades 9-12 education and graduation requirements, dropout recovery, alternative education, or serving at-risk populations;
• Experience in high-growth or startup environments;
• Knowledge of school funding and charter school business models in Ohio and at the Federal level;
• This position is Ohio-based with occasional travel within the state. Ohio residency must be established within the first year of employment.

CULTURE & ENVIRONMENT FIT

• Has built within organizations, not just inherited scale — understands startup/growth dynamics;
• Sees founder engagement as an asset, not an obstacle to effectiveness;
• One for all and all for one, we win as a team, we lose as a team.

Benefits

COMPENSATION & BENEFITS

This position offers a competitive salary range of $150,000 - $200,000, and robust benefits including medical, dental, retirement (STRS Ohio) and potential relocation allocation. More details can be provided upon request.

TO APPLY

Please submit a resume online at https://apply.workable.com/j/948FD3FE91/.

ChallengeU is an equal opportunity employer and an organization that values diversity. Recruiting staff to create an inclusive organization is a priority, and we encourage applicants from all backgrounds. Candidates are evaluated solely on their qualifications to perform the work required.