At Rootly we are on a mission to be the go-to way companies respond when things go wrong, helping every organization be more reliable. We do this by building an industry-leading incident management platform that allows companies around the world to consistently and quickly resolve incidents. Customers love Rootly. See why our customers have reviewed us 5 stars on G2 We conduct monthly financial reviews as a team so everyone has a pulse on the health of the business and publish what we are building in our weekly changelog We’re hiring a Senior AI Engineer to lead the development of this new AI‑driven reliability assistant. This isn’t a traditional ML role – we’re not training custom models (yet). Instead, this is about LLM engineering and AI agent development, leveraging existing AI technologies (LLMs, vector embeddings, semantic + hybrid search, vector databases) to create a non‑deterministic product that provides real value to engineers and ultimately reduces the time to resolve incidents. If you thrive in a rapid‑moving environment where you build, ship, and iterate quickly, this is the role for you. Own and drive the development of an AI‑powered reliability assistant that retrieves relevant context from disparate data sources (observability tools, GitHub, deployment histories, past incidents, playbooks, etc.). Develop LLM‑powered features that transform raw data into actionable insights for engineers responding to incidents. Implement evaluation frameworks to measure AI performance in real‑world scenarios and refine workflows accordingly. Stay on the cutting edge of AI, keeping up with advancements in LLMs, retrieval‑augmented generation (RAG), agent frameworks, and related technologies.



Collaborate closely with product and engineering teams to iterate quickly, ship features, and refine AI‑driven workflows. Raise the bar and inspire those around you—bringing energy, passion, and an obsessive focus on quality and impact. 5+ backend engineering background – you’ve built and shipped complex, production‑grade systems. Experience working with LLMs – you’ve built AI‑powered applications, experimented with agents, and understand the nuances of prompt engineering, embeddings, and search. Deep familiarity with AI development frameworks – you know the current best practices and tools for building intelligent agents. Experience with AI system evaluation – you understand how to assess AI performance in production and refine models and workflows accordingly. Passionate about AI and reliability engineering – you stay up to date on the latest AI research, trends, and technologies. Bias for action – you move fast, ship fast, and optimize for high‑velocity impact. Great taste – you don’t just build software; Strong communication skills – you can explain complex technical concepts simply and effectively. Competitive compensation and early equity in a fast‑growing, venture‑backed company. Comprehensive medical, dental, and vision coverage. 3 weeks of vacation, plus unlimited sick and mental health days, and a company‑wide end‑of‑year shutdown to recharge. $500 stipend for home office setup. We aim to create an environment where every team member at Rootly feels like they belong so they can have a greater impact on our business and customers. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status. #

📌 Remote AI Engineer (Toronto)
🏢 Rootly
📍 Toronto