Director of Engineering, Search, Recommendations, Discovery and Distribution at Upwork

This role is designed for a seasoned engineering leader with over 10 years of experience specifically in large-scale search, discovery, and recommendation systems. You are the ideal candidate if you possess deep technical mastery of vector retrieval and relevance modeling, combined with the leadership maturity to manage multiple teams of managers and technical leads. A standout aspect of this position is its central role in the company's AI-driven evolution. You will be building the infrastructure that powers the future of work, including generative and retrieval-based models at a global scale. Note that this is a **hybrid role based in Toronto (3 days in-office)** and will initially be managed through a hiring partner while the company establishes its local operational hub. **You might be a good fit if you:** * Have a proven track record of leading engineering organizations focused on SEO/SEM, ranking, and distribution systems. * Possess "Adaptive-level AI fluency," with the ability to integrate AI into engineering workflows and iterate on prompt strategies. * Thrive in high-ownership environments where you drive architectural decisions for low-latency, high-performance pipelines. * Are comfortable navigating a transition from a partner-managed role to direct employment as the Toronto hub scales.