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Director of Learning, 2 Hour Learning (Remote) - Job Opportunity at Crossover

Mississauga, Canada

Full-time

Executive

Posted: April 16, 2025

Remote

USD 200,000 per year

Key Responsibilities

Lead strategic development and optimization of AI-driven learning ecosystem across multiple campuses

Drive data-informed decision making through learning analytics and student performance metrics

Direct cross-functional teams including learning engineers, data scientists, and instructional designers

Oversee implementation of personalized learning pathways leveraging AI technology

Manage direct student engagement initiatives to gather actionable feedback and insights

Requirements

Education

Master's degree or higher in Educational Science, Learning Science, Psychology, Psychometrics, Instructional Design, or related field

Experience

Senior leadership experience in education or EdTech required

Required Skills

AI technology implementation in educational contexts Learning science principles Data-driven educational approaches Cross-functional team leadership Complex project management Communication of technical concepts

Sauge AI Market Intelligence

Industry Trends

The shift toward AI-driven, teacher-less education represents a significant disruption in the traditional education sector, with potential to reshape the $7 trillion global education market. This trend is accelerated by the increasing acceptance of remote learning post-pandemic and the advancement of AI capabilities in personalized instruction. The convergence of EdTech and AI is creating a new category of educational leadership roles that blend traditional pedagogical expertise with technical competencies. This hybrid skill set is increasingly valuable as education institutions seek to modernize their approach. The focus on measurable outcomes through standardized testing (AP exams, MAP assessments) reflects the growing emphasis on data-driven education and accountability in learning outcomes.

Salary Evaluation

The offered salary of $200,000 is competitive for an executive EdTech position, falling within the expected range of $180,000-$250,000 for similar roles. The compensation reflects the unique combination of educational leadership and AI expertise required.

Role Significance

Based on the scope and multiple campus oversight, likely leading a team of 15-25 professionals across learning engineering, data science, and instructional design disciplines.

Executive-level position with strategic oversight of educational outcomes and technology implementation across multiple campuses. The role carries significant autonomy and accountability for student achievement metrics.

Key Projects

Development and scaling of AI-driven personalized learning algorithms Implementation of data analytics infrastructure for tracking and optimizing student outcomes Creation of adaptive assessment systems integrated with standardized testing preparation Design of motivation and engagement frameworks for teacher-less learning environments

Success Factors

Ability to balance innovation with proven educational principles while maintaining focus on measurable student outcomes Strong change management skills to drive adoption of non-traditional learning approaches Deep understanding of both educational psychology and AI capabilities to create effective learning systems Data-driven decision-making expertise combined with student-centric approach to development

Market Demand

Very High - The intersection of AI and education is experiencing rapid growth, with demand for leaders who can bridge both domains exceeding current supply. This role represents an emerging category of educational leadership positions that are expected to see increasing demand over the next 5-10 years.

Important Skills

Critical Skills

AI/ML expertise specifically applied to educational contexts - Essential for developing and optimizing learning algorithms Learning science and educational psychology - Critical for ensuring AI implementations support effective learning outcomes Data analytics and interpretation - Necessary for measuring and improving student achievement metrics Change management and stakeholder communication - Vital for driving adoption of innovative learning approaches

Beneficial Skills

Experience with standardized testing and assessment design Background in motivation theory and student engagement Knowledge of learning management systems and educational software development Understanding of educational policy and compliance requirements

Unique Aspects

The teacher-less learning model represents a radical departure from traditional education approaches, positioning this role at the forefront of educational innovation.

The combination of AI technology and learning science in a production environment offers unique opportunities for large-scale experimentation and validation of educational theories.

Direct access to student feedback and performance data allows for rapid iteration and optimization of learning approaches.

Career Growth

2-3 years in role typically required before progression to C-suite positions, with significant opportunity for lateral movement into broader educational technology leadership roles

Potential Next Roles

Chief Learning Officer Chief Educational Technology Officer Chief Academic Officer EdTech Startup Founder/CEO

Company Overview

Crossover

Crossover appears to be positioning 2 Hour Learning as a disruptive force in education, leveraging AI to fundamentally reshape traditional learning models. The company's focus on measurable outcomes and technology-driven solutions suggests a well-funded, ambitious venture.

Early stage but innovative player in the emerging AI-driven education sector, with potential to significantly impact the traditional education market through its teacher-less learning model.

While based in Mississauga, the remote nature and multiple campus oversight suggests a broader North American or global operational scope.

Fast-paced, innovation-focused environment with emphasis on data-driven decision making and bold experimentation. The culture appears to value results over traditional educational approaches.

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Director of Learning, 2 Hour Learning (Remote) - Job Opportunity at Crossover

Key Responsibilities

Requirements

Education

Experience

Required Skills

Sauge AI Market Intelligence

Industry Trends

Salary Evaluation

Role Significance

Key Projects

Success Factors

Market Demand

Important Skills

Critical Skills

Beneficial Skills

Unique Aspects

Career Growth

Potential Next Roles

Company Overview

Crossover

Data Sources & Analysis Information

Job Listings Data

Sauge AI Market Intelligence