Senior AI Engineer

Mosaic.tech; Toronto; On-site; CAD 120,000 - 180,000; Full time

Benefits offered by this job

Equity in a fast-growing company

Comprehensive medical/dental/vision

Three weeks of vacation + sick days

Home office stipend

Year-end shutdown to recharge

Job summary

Rootly is hiring a Senior AI Engineer to lead the development of our AI-driven reliability assistant. You will own the end-to-end implementation of LLM-powered features and agent frameworks, ensuring fast delivery and high impact for incident response teams.

You will work on integrating data sources, evaluating AI performance, and staying at the cutting edge of AI technology. A fast-paced environment awaits engineers who ship with quality and urgency.

Qualifications

• 5+ years of backend engineering experience building production systems.
• Experience with large language models and AI-powered applications, including agents and embeddings.
• Strong familiarity with AI development frameworks and best practices.
• Experience evaluating AI systems in production and refining workflows.
• Passion for AI and reliability engineering; proactive problem solving.

Responsibilities

• Own and drive development of an AI-powered reliability assistant that pulls context from diverse sources (observability, GitHub, deployment histories, incidents, playbooks).
• Develop LLM-powered features turning raw data into actionable insights for engineers handling incidents.
• Implement evaluation frameworks to measure AI performance in real-world scenarios and improve workflows.
• Stay current with AI research and technologies (LLMs, RAG, agent frameworks).
• Collaborate with product and engineering teams to ship features quickly and scale AI-driven workflows.
• Think in systems to ensure solutions scale today and tomorrow.
• Act with ownership, fix problems, and push work forward with urgency.

Skills

Backend engineering

LLMs

AI agent development

Prompt engineering

System design

Communication

Tools

Vector databases

Embeddings

Retrieval-augmented generation

Job description

ABOUT ROOTLY

At Rootly https://rootly.com/, 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 https://www.g2.com/products/rootly-manage-incidents-on-slack/reviews.

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 https://rootly.com/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

• 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.

WHY 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.
• $500 stipend for home office setup.
• A fast‑moving, high‑impact environment where your leadership and ideas directly shape the future of the company.

Equal Opportunity

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.