Senior Software Engineer, AI at Toast — NeverHard

Job Description Toast is recruiting on behalf of this company for a Senior Software Engineer, AI to join their Engineering team in Toronto. They are looking for an experienced backend engineer who is excited to build and optimize LLM-powered systems that help users uncover meaningful business insights. Responsibilities Design, build, and maintain backend systems that power LLM-driven and agentic workflows Develop retrieval pipelines, orchestration layers, and multi‑step agent architectures that support scalable AI‑powered search experiences Lead the evaluation of agentic systems using automated, offline, and human‑in‑the‑loop frameworks to measure relevance, quality, latency, and task success Improve retrieval and ranking systems across hybrid retrieval, re‑ranking, query rewriting, and post‑retrieval synthesis Optimize LLM‑powered workflows for speed, accuracy, reliability, and production readiness Own technical projects from concept through launch, including experimentation strategy, architecture decisions, and operational excellence Collaborate closely with product, infrastructure, and data teams to align technical solutions with user needs and business goals Stay current with advances in LLMs, retrieval systems, and agentic reasoning, and apply relevant developments to product and engineering work Contribute to engineering best practices that support maintainability, observability, testing, and continuous delivery Requirements 5+ years of experience building and operating backend systems in production Strong experience in at least one of the following areas: search and retrieval, data pipelines, distributed systems, or API‑driven service architectures 2+ years of hands‑on experience working with search, retrieval, or ranking systems Experience building or evaluating LLM‑powered or agentic systems, including retrieval‑augmented generation or multi‑step workflows Strong software engineering fundamentals with the ability to write clean, maintainable, and well‑tested code Proficiency in Python and experience with backend frameworks, APIs, and production infrastructure Familiarity with vector databases and search platforms such as FAISS, PGVector, Pinecone, Weaviate, Elasticsearch, or OpenSearch Experience with cloud platforms such as AWS, GCP, or Azure in environments with scale, low‑latency requirements, and high availability Experience using AI coding tools to improve development workflows A customer‑focused mindset with the ability to connect technical decisions to user outcomes Demonstrated ability to lead projects, make sound architectural decisions, and support the growth of others on the team Benefits Competitive compensation with a salary range of CA$145,000–CA$183,000, plus equity Extended health and dental coverage starting from day one Employee Stock Option Plan for full‑time employees Flexible vacation policy designed to support rest and balance Career development support through coaching, feedback, and performance reviews Access to high‑quality equipment and tooling Hybrid work model with in‑office collaboration in Toronto on designated days Opportunities to work closely with leadership and contribute to meaningful technical direction A workplace that values belonging, authenticity, accessibility, and professional growth An inclusive hiring approach that considers potential, transferable experience, and equivalent backgrounds #J-18808-Ljbffr