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

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