Senior AI Engineer at Rootly (S21) $140K - $180K CAD AI-native on-call and incident response carefully crafted to help modern teams prevent and resolve incidents faster Toronto, Ontario, Canada (Hybrid) / Remote (Toronto, ON, CA) Full-time US citizenship/visa not required 6+ years About Rootly At Rootly, we are a mission to be the go-to way companies respond when things go wrong, helping every organization be more reliable. We do this by building an industry leading incident management platform that allows companies around the world consistently and quickly resolve incidents. We are not simply transforming an industry, we are carving an entirely new +$B segment ourselves and need incredible talent to achieve this ambitious goal together. Customers love Rootly. Some of the fastest growing companies around the world such as NVIDIA, Figma, Canva, Tripadvisor, Squarespace and more rely on Rootly to power their critical incident management process. They obsess over our delightful enterprise-ready platform and unique partnership model. See why our customers have reviewed us 5 stars on G2. Investors love Rootly. We are backed by some of the most respected funds in the world from Y Combinator to operators like the CTO of Dropbox and GitHub. We'd be happy to disclose our entire funding and profitability picture live during the interview. As a culture we relentlessly put transparency first. 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. About the role Skills: Tailwind, Ruby on Rails About Rootly 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. We are not simply transforming an industry, we are carving an entirely new +$B segment ourselves and need incredible talent to achieve this ambitious goal together. Customers love Rootly. Some of the fastest growing companies around the world such as NVIDIA, Figma, Canva, Tripadvisor, Squarespace and more rely on Rootly to power their critical incident management process. They obsess over our delightful enterprise-ready platform and unique partnership model. See why our customers have reviewed us 5 stars on G2. Investors love Rootly. We are backed by some of the most respected funds in the world from Y Combinator to operators like the CTO of Dropbox and GitHub. We'd be happy to disclose our entire funding and profitability picture live during the interview. As a culture we relentlessly put transparency first. 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. About the Role 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. 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. If you thrive in a fast-moving environment where you build, ship, and iterate quickly, this is the role for you. What You'll Do 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. What You'll Need We care more about execution, ownership, and impact than fancy degrees or FAANG experience. If the following resonates with you, we want to hear from you: Strong 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. Why Rootly? We’re not just another startup. We’re building something category-defining and want teammates who crave ownership, love solving hard problems, and thrive in a high-bar, high-impact environment. Here’s what you can expect when you join Rootly: 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. MacBook Pro of your choice to help you do your best work. $1,000 annual stipends for health and wellness and home office setup. Learning and development budget at your discretion to support your growth. A fast-moving, high-impact environment where your leadership and ideas directly shape the future of the company. If this sounds like the kind of challenge and opportunity you’re looking for, apply now and let’s build something great together. Rootly is an equal opportunity employer. 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. Technology Rails, Postgres and Redis in the backend Sidekiq for background jobs Hosted on AWS with Heroku Terraform for infrastructure as code GitHub, Slack, Notion