Chief Technology Officer

OVERVIEW

We are seeking a visionary and execution-driven Chief Technology Officer (CTO) to lead the technology organization for our rapidly scaling SaaS platform in the education technology (edtech) sector. This individual will oversee a team of 40+ engineers, product developers, and data specialists, driving innovation across our mobile applications and back-end systems.

The CTO will be responsible for defining and executing the company's technology strategy, ensuring scalable architecture, operational excellence, and a forward-looking approach to AI integration that enhances both current products and future capabilities.

KEY RESPONSIBILITIES

Technology Leadership & Vision

• Define and execute the long-term technology vision and roadmap in alignment with overall business and product strategy.
• Evolve the company's SaaS platform to ensure high scalability, security, and performance across web and mobile applications with a large, active user base.
• Foster a culture of innovation, technical excellence, and continuous learning within a fast-paced engineering environment.

Product & Platform Development

• Oversee the implementation of the product roadmap across a modern full-stack architecture.
• Collaborate with Product Management and UX teams to deliver intuitive, impactful user experiences across platforms.
• Ensure high availability, reliability, and maintainability of the back-end infrastructure and mobile app ecosystem.

AI-First Development & Data Strategy

• Champion an AI-first strategy for all new product initiatives, integrating AI technologies to augment and personalize the learning experience.
• Architect and implement AI-ready data storage strategies to support large-scale model development and real-time learning insights.
• Lead efforts in LLM and GPT-based product features, including fine-tuning, prompt engineering, and model integration.
• Oversee initiatives in data preparation, model training, and deployment pipelines to power new intelligent capabilities.

Team Management & Organizational Leadership

• Lead, mentor, and scale a high-performing technology organization of 40+ across engineering, DevOps, data, and AI research functions.
• Establish clear performance metrics, career paths, and cross-functional collaboration frameworks.
• Build and maintain a strong engineering culture rooted in accountability, creativity, and technical mastery.

Security, Compliance, and Infrastructure

• Ensure all systems meet modern data privacy, security, and compliance standards (FERPA, GDPR, COPPA, etc.).
• Oversee cloud infrastructure management, cost optimization, and reliability engineering.

REQUIRED EXPERIENCE

• 10+ years of experience in software engineering and technology leadership roles.
• Proven success leading teams of 30+ engineers in SaaS or consumer-scale software products.
• Deep understanding of full-stack modern architectures (React, , Python, microservices, etc.) and cloud infrastructure (AWS, GCP, or Azure).
• Track record of delivering and scaling mobile apps with large active user bases.
• Experience implementing AI/ML-driven product features, including data infrastructure, model development, and integration.
• Hands-on familiarity with LLM frameworks (e.g., OpenAI, Anthropic, Hugging Face) and vector database architectures.
• Strong grasp of data strategy, including pipelines, storage, and governance for machine learning use cases.

PREFERRED EXPERIENCE

• Prior experience in EdTech, learning management systems, or student engagement platforms.
• Background in AI productization — translating research and prototypes into production-ready solutions.
• Strong communication skills and ability to interface effectively with executives, investors, and non-technical stakeholders.

COMPENSATION AND BENEFITS

• Competitive base salary and equity participation.
• Comprehensive health, dental, and vision coverage.
• Flexible hybrid work environment (Boston-based HQ).
• Professional development support and access to AI/ML learning programs.

WORK LOCATION

This is a hybrid remote position based in the Greater Boston area. While much of the work can be completed remotely, this role requires regular in-person collaboration with key stakeholders at our Cambridge, MA office. Candidates should be within commuting distance and comfortable coming on-site as needed for meetings, planning sessions, and team activities.

WHY JOIN US

You'll be at the forefront of shaping the next generation of education technology — leading a team that merges cutting-edge AI with impactful learning experiences for millions of users worldwide. This is an opportunity to define the technical future of a platform transforming how people learn and grow.

Ready Education is an Equal Employment Opportunity and Affirmative Action Employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, or disability status.