Chief Technology Officer (CTO) – EdTech / Education (Remote | Equity Ownership)

About the Role American AI & Automation (AAIA) is seeking a Chief Technology Officer (CTO) for our Education Division — a hands-on builder who has architected, scaled, and launched LMS or SIS platforms and previously held a leadership role at a major LMS company (e.g., Blackboard, Canvas, PowerSchool, Infinite Campus). This is not a symbolic leadership post. We need a CTO who understands both the infrastructure of education systems and the power of AI/ML automation to reinvent them. Someone who can bridge real-world district needs with advanced data models, predictive analytics, and personalized learning engines. Key Responsibilities: AI-Driven Platform Architecture Lead design and development of next-generation AI-powered LMS and SIS platforms within AAIA’s automation ecosystem. Architect scalable data systems that enable adaptive learning, predictive analytics, and student performance modeling. Integrate with major education platforms (Canvas, Blackboard, PowerSchool, Infinite Campus, etc.) through intelligent APIs and automation pipelines. Ensure compliance with FERPA, COPPA, and state-level education data privacy frameworks. Build infrastructure optimized for secure data ingestion, real-time insights, and automated decision support. Hands-On Technical Leadership Contribute directly to system architecture and code decisions early on. Define technical standards, automation workflows, and scalable delivery playbooks. Evaluate and implement ML models that drive content recommendations, engagement analytics, and administrative automation. Maintain alignment between AI product vision and real classroom needs. Strategic Technology Leadership Serve as the AI/Tech voice on the executive team, shaping AAIA’s education roadmap. Partner with the CPO to align user experience with intelligent system design. Guide data strategy for multi-institution learning networks and analytics platforms. Support investor and client discussions by demonstrating AAIA’s AI moat and technical differentiation. Team Building & Scaling Recruit and lead engineers skilled in EdTech, AI, and data systems. Build teams that can deploy AI models into production within complex education environments. Implement rigorous DevOps, QA, and security practices for enterprise-scale delivery. Client & Stakeholder Engagement Collaborate with superintendents, CIOs, and university leaders to design high-impact AI solutions. Communicate complex architectures in practical terms to non-technical stakeholders. Support executive partnerships, grant initiatives, and large-scale integrations. Must-Have Previously held a senior role at a major LMS company (e.g., Blackboard, Canvas, PowerSchool, or similar). Direct experience building or scaling LMS/SIS systems with AI or advanced data capabilities. Proven track record delivering education platforms at scale (thousands of users or multiple institutions). Fluency in AI/ML architectures, data engineering, and cloud-native systems. Understanding of education workflows, compliance, and integrations. Startup or 0→1 product experience strongly preferred. Compensation & Equity Equity: 25–40% tied to Education Division performance and revenue. Option to transition into salary + equity + performance incentives as company scales. Unlimited upside tied to delivery and growth. Why AAIA Real autonomy to define and execute the technical direction of AI in education. Backed by high-velocity product and leadership teams. Ability to build at the intersection of AI, automation, and education systems. Remote-first, travel as needed for partnerships and clients. If you’ve built LMS/SIS systems and know how to layer AI into the foundation of education, this is your seat. Send proof of platforms shipped and results achieved. Not résumés — outcomes. Job Types: Full-time, Contract Pay: $100.00 - $400.00 per hour Benefits: Flexible schedule Work Location: Remote