Chief Technology Officer (CTO) – EdTech Platform, AI & Systems Leadership - Contract to Hire

Role Overview We are an EdTech company seeking a seasoned, execution-driven Chief Technology Officer (CTO) to own and lead all technology across the organization. This includes the architecture, launch, and long-term evolution of a core web application, as well as the internal systems, data infrastructure, AI capabilities, security standards, and engineering processes that power our educational programs. The CTO will be responsible for designing and maintaining a robust EdTech platform that serves students, parents, tutors, and internal teams—while ensuring the technology scales responsibly, securely, and efficiently as programs and demand grow. The ideal candidate is both strategic and hands-on, capable of making high-stakes architectural decisions, guiding engineers, and translating educational and operational needs into reliable, scalable systems. Core Responsibilities & Mandate The CTO will have full ownership of the following areas: 1. EdTech Platform & Web App Ownership Architect, build, launch, and continuously improve the primary EdTech web application Ensure the platform supports multiple user types (students, parents, tutors, administrators) with appropriate permissions and workflows Own frontend, backend, APIs, databases, hosting, and cloud infrastructure Define and manage the technical roadmap, release cycles, and system scalability plans Ensure performance, uptime, security, and reliability under increasing usage 2. Technology Strategy & Systems Architecture Define and execute a long-term technology roadmap aligned with academic outcomes and business growth Design systems that support tutoring operations, scheduling, attendance, reporting, assessments, and communications Evaluate, select, and integrate third-party tools (video platforms, scheduling tools, CRM, analytics, LMS components) Reduce operational friction by replacing manual workflows with scalable systems Establish engineering standards, documentation practices, and technical governance 3. AI & Automation Leadership (Applied, Not Experimental) Identify high-impact opportunities for AI within an EdTech context Implement AI-powered features such as automation, analytics, progress insights, reporting, forecasting, and internal decision support Use AI tools to accelerate development, reduce operational overhead, and improve platform intelligence Ensure AI is applied ethically, transparently, and responsibly—especially in student-facing environments Define clear guidelines for data usage, privacy, and AI governance 4. Data, Security & Compliance Own data architecture, storage, access controls, and reporting pipelines Ensure compliance with student data privacy standards and applicable regulations Implement security best practices across infrastructure, applications, and integrations Build reliable monitoring, backup, and disaster-recovery processes Ensure system integrity and auditability as the platform scales 5. Engineering Team & Execution Leadership Hire, manage, and mentor engineers, developers, and technical contractors Coordinate with external vendors and technology partners Review architecture and code quality to ensure maintainability and scalability Set clear expectations, delivery timelines, and accountability across technical initiatives Build a culture of ownership, clarity, and disciplined execution Experience & Qualifications 5+ years of experience in senior technical leadership roles (CTO, Head of Engineering, Lead Architect) Proven track record of building and scaling production web applications Strong proficiency with AI tools and applied AI systems Deep understanding of full-stack development and cloud infrastructure Ability to translate educational, operational, and business needs into technical execution Experience operating in fast-moving or growth-stage environments Preferred Background in EdTech, tutoring platforms, or learning-focused systems Experience with LMS components, scheduling systems, and reporting dashboards Familiarity with privacy-sensitive or youth-facing platforms Startup or founder-led company experience What Success Looks Like in This Role A stable, scalable EdTech web application supporting core programs Integrated internal systems that reduce manual operations AI-enabled workflows that improve efficiency and insight Clear technical documentation and standards Technology that directly improves educational delivery and organizational growth Engagement & Structure Full-time or fractional (with clearly defined ownership and milestones) Remote-friendly Apply tot his job Apply To this Job