Who you are

- If you thrive in a fast-moving environment where you build, ship, and iterate quickly, this is the role for you

- 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; you craft experiences that feel polished and intuitive

- Strong communication skills - you can explain complex technical concepts simply and effectively

- Product instinct - you don’t just take tickets - you challenge ideas, see the bigger picture, and contribute to the end-to-end user journey

What the job involves

- We’re hiring a Senior AI Engineer to lead the development of this recent 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

- As an early engineer at Rootly,



you will have full ownership over this initiative and play a pivotal role in shaping both the product and company

- 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

- Think in systems, not just features - ensuring that what we build today scales effectively for tomorrow

- Act like an owner - when you see a problem, you fix it. When you don’t know how, you figure it out. You drive work forward, proactively and with urgency

- Raise the bar and inspire those around you—bringing energy, passion, and an obsessive focus on quality and impact

Benefits

- Medical, dental, vision, and life coverage for you and your dependents

- Flexible PTO, plus company holidays, team off-sites, and a year-end shutdown to recharge

- Meaningful equity in a high-growth company, and 401(k) matching for US employees

- Hybrid work (we hire across the US, Canada, Europe, and Singapore)

- Free lunches at HQ
- Fast-moving, high-impact environment where you have autonomy to own big problems from day one

- Top-tier hardware and tools, plus an annual stipends for home offices

📌 Senior AI Engineer (Toronto)
🏢 Rootly
📍 Toronto