AI-First Lead Engineer - EZRA

Job Role: AI-First Lead Engineer Location: Ontario - Remote Who we are We believe everyone can be better with a coach... and we won’t stop until we get there. Coaching changes people’s lives. It helps them be happier and more productive in their work. It turns entire companies into more inclusive, more productive places to be. That’s why we’ve made it easy for more people – not just those at the top – to benefit from the world’s best coaches. This is true of our EZRA team. We believe a happy team is a productive one. We help our people grow, to care deeply about and be proud of what we do. The Role As an AI-First Lead Engineer, you will own the end-to-end design, quality, and reliability of EZRA’s AI capabilities, shaping how AI powers our product experience. Reporting to the VP of Engineering, you will partner cross-functionally to deliver scalable, safe, and high-performing AI solutions that drive measurable user impact. A core focus of this role is leading EZRA’s fully AI-augmented development that represents a deliberate departure from the approach taken traditionally. This stream needs a different kind of developer: someone comfortable directing AI tools, thinking architecturally, and producing clear recommendations, not just code. You will help define how this way of working takes shape at EZRA, figuring out multi-agent patterns and long-running pipelines alongside leadership rather than waiting for a playbook to exist. What You'll Do Define and lead the design of AI solutions, including model selection, prompting strategies, orchestration patterns, and fallback mechanisms Own AI evaluation frameworks, establishing quality metrics and driving continuous improvement through experimentation and iteration Implement and maintain safety guardrails, mitigating risks such as prompt injection, data leakage, and unsafe outputs Optimize AI systems for performance, latency, cost, and reliability, including observability and incident response readiness Provide technical leadership, mentoring engineers and setting best practices for AI-enabled development across teams Lead AI-augmented development in the Reimagine stream, directing AI tools architecturally and translating outputs into clear, defensible technical decisions Design and evolve multi-agent patterns and long-running pipelines from first principles, working alongside leadership in a genuinely greenfield environment Critically evaluate AI-generated code for correctness, security, and enterprise suitability for shipping solutions fast without cutting corners on quality About you 8+ years of engineering experience, including 5+ years delivering ML/AI solutions into production environments Strong proficiency in Python and hands-on experience with modern ML/LLM tooling, orchestration frameworks, and APIs Experience designing and implementing evaluation frameworks with measurable quality metrics Practical knowledge of AI safety risks and mitigation techniques (e.g., hallucinations, prompt injection, data leakage) Experience optimizing systems for performance, cost efficiency, and scalability in production environments Experience working with cross-functional teams to translate product requirements into technical solutions Strong TypeScript/Node fundamentals: able to critically evaluate AI-generated code, not just ship it Actively building with LLMs already: shipping product features, agentic workflows, or clearly headed there fast Strong judgment on the speed/quality/security trade-off, particularly in an enterprise context where corners cannot be cut Comfortable being early: you experiment constantly, have opinions, and can help define patterns rather than waiting for a playbook to exist Life at EZRA Your Own World-class coach to help you grow personally and professionally. Coaching for Friends and family because coaching is a gift worth passing on. Charity Days to support the causes close to your heart - because doing good feels good. Learning Budget to fuel your curiosity. If it helps you grow, we’re in. Weekly Wellbeing Hour just for you. No meetings. No emails. Just space to breathe, reflect, or reset. Regional benefits flex to fit your location and lifestyle. A welcoming place to do your best work. Comfortable, collaborative and inclusive. We’re an equal opportunity employer dedicated to building a diverse team that reflects the communities in which we work, where everyone has a voice and feels able to be themselves. We believe that diversity strengthens to our culture and business. Valuing uniqueness and respecting our differences means we grow faster, become better, and achieve more. In the spirit of transparency, credentials are verified through background checks conducted upon conditional employment, in accordance with applicable laws.