Director of Software Engineering, Loopio

• 10+ years of experience in software development, including 3–5+ years in engineering leadership roles
• Proven success in managing and scaling multiple engineering pods and/or other managers
• Deep experience in search infrastructure, information retrieval, or ML/NLP applications
• Technical fluency in building and optimizing large-scale distributed systems
• Familiarity with semantic search, vector embeddings, hybrid search strategies, or LLM-enhanced search
• Excellent communication skills, with the ability to align technical initiatives with business outcomes
• Track record of fostering inclusive, high-trust team environments
• Bachelor’s or Master’s degree in Computer Science or related field—or equivalent industry experience

Desirable

• We’re looking for a Director of Software Development to lead our Library Mission Team, which is responsible for the content retrieval systems that power the core of the Loopio platform
• This includes our hybrid search capabilities, OpenSearch infrastructure, and emerging investments in natural language search, semantic indexing, and ML-enhanced content retrieval
• This is a strategic and technical leadership role ideal for someone with deep expertise in content discovery and retrieval systems, experience with natural language and search ranking models, and the ability to manage multiple pods—including other engineering managers
• You’ll work closely with leaders across Product, Data Science, Infrastructure, and Design to deliver scalable, intelligent systems that enhance how our customers access and organize content
• Lead and grow multiple engineering pods, including supporting other managers and technical leads
• Foster a high-performing, inclusive engineering culture centered on accountability, autonomy, and craft
• Mentor and develop engineering leaders, helping them grow through coaching and clear feedback
• Attract, retain, and nurture top technical talent across Canada, India, and the UK
• Drive the architecture and evolution of Loopio’s content retrieval and hybrid search platform
• Partner with Data and ML teams to integrate semantic search, ranking models, and NLP-enhanced retrieval
• Make technical decisions that balance short-term velocity with long-term scalability and maintainability
• Provide hands-on architectural guidance, ensuring strong design patterns and system reliability
• Oversee planning, prioritization, and execution across multiple pods, ensuring timely delivery and alignment to roadmap goals
• Collaborate with Product and Design partners to translate customer needs into intelligent, performant features
• Proactively manage technical dependencies, risks, and cross-team coordination
• Champion high-quality engineering practices, observability, testing, and performance optimization
• Lead incident response and root cause analysis for content retrieval systems
• Continuously refine workflows, tooling, and delivery processes for team efficiency
• Serve as a key voice in strategic planning and technical vision for Library-related initiatives
• Collaborate with Data, Infrastructure, and Platform teams on scalable solutions for data ingestion, indexing, and retrieval
• Effectively communicate technical decisions to stakeholders across the business
• Explore and implement ML techniques to improve search quality, semantic understanding, and ranking
• Keep up with trends in search infrastructure (e.g., OpenSearch/Elasticsearch), vector databases, LLM integration, and AI-enhanced UX
• Encourage innovation and experimentation in how users interact with large content libraries