2627 Founding Technical Lead / CTO

RedBranch Executive Search & Recruitment Inc.; Toronto; On-site; CAD 180,000 - 280,000; Full time

Job summary

RedBranch Executive Search & Recruitment Inc. is seeking a Founding Technical Lead / CTO to architect and build the core AI platform for a dynamic startup in Toronto.

This hands-on leadership role will drive critical technology decisions, shape the product architecture, and deliver scalable, secure AI-powered experiences. The ideal candidate blends deep technical expertise with product intuition, thrives in a fast-moving, ambiguous environment, and can lead from the front while aligning

Qualifications

• Experience building and shipping production-grade software in early-stage startups.
• Hands-on with LLM APIs, RAG systems, vector search, and production AI workflows.
• Strong full-stack skills across React, Typescript, Node.js, Python and backend API design.
• Security and data privacy mindset for high-trust environments.
• Product intuition to translate workflows into structured product experiences.

Responsibilities

• Build and architect the core AI platform, developing secure, scalable AI systems.
• Own technical architecture and infrastructure decisions across app and AI infra.
• Develop secure, auditable workflows and AI experiences with transparent outputs.
• Turn early-stage concepts into production-ready products with the founding team.
• Establish engineering and security standards balancing AI with user experience.

Job description

We have an exciting opportunity for a Founding Technical Lead / CTO with an innovative AI technology startup. This is a highly hands-on role for a technical leader who will play a key role in shaping the company’s architecture, making critical technology decisions, and building the core systems that will power the next stage of the product. The ideal candidate combines deep technical expertise with strong product thinking and thrives in an entrepreneurial, fast-paced environment where ambiguity is part of the opportunity.

Key Responsibilities

• Build and architect the core AI platform, developing secure, scalable, and reliable AI systems that power the company’s product experience.
• Own technical architecture and infrastructure, making key decisions across application architecture, backend systems, AI infrastructure, data management, and scalability.
• Develop secure, auditable legal workflows and AI experiences, ensuring sensitive information is protected while making AI outputs transparent, traceable, and easy to verify.
• Turn early-stage concepts into production-ready products, working closely with the founding team to rapidly move from prototypes to polished, scalable solutions.
• Establish engineering and security standards, setting best practices for code quality, infrastructure, privacy, reliability, and balancing AI capabilities with enterprise-grade security and user experience.

Requirements

• Experience building and shipping production grade software in early stage environments. 0 - 1 startup execution
• Hands on experience working with LLM APIs, RAG systems, vector search, AI evaluation and production AI workflows
• Strong full stack ability across modern web application development including React, Typescript, Node.js, Python and backend API design
• Systems debugging and reliability
• Security and Sovereignty mindset. A strong appreciation for data privacy, compliance, secure data handling, and building AI systems for high-trust professional environments
• Product Intuition. Ability to translate complex professional workflows into clear, structured product experiences that feel trustworthy, organized, and useful.