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. Rootly is building the AI-native future of incident management, and we need someone who can push our AI to its limits before our customers do.

As our AI Quality Engineer, you'll own the evaluation and optimization of Rootly's agentic AI features -- designing test scenarios, running adversarial prompts, interpreting outputs, and working directly with engineering and product to close the loop on performance. You'll spend your days thinking like an attacker, a confused user, and a power user all at once -- probing how our AI agents reason, make decisions, and handle edge cases across complex incident workflows. Design and execute prompt-based test scenarios that cover happy paths, edge cases, and adversarial inputs across Rootly's agentic AI features Evaluate AI outputs for accuracy, relevance, consistency, and alignment with expected workflow behaviour structured test libraries, scoring rubrics, and regression suites to track AI performance over time Partner with Product and Engineering on new AI feature releases, contributing to acceptance criteria and quality gates before launch Define and track quality metrics (accuracy rates, failure frequency, regression trends)



and report findings to stakeholders Stay current on LLM evaluation techniques, prompt engineering best practices, and agentic testing methodologies 5 years in QA, product operations, AI/ML evaluation, or a closely related role Hands‑on experience testing or evaluating LLM‑powered or agentic AI products Strong prompt engineering instincts -- you understand how wording, context, and structure affect model behaviour Comfortable writing scripts or working with evaluation tools (Python a plus; not required to be a full-stack engineer) able to translate AI behaviour findings for both technical and non-technical audiences Familiarity with incident management, DevOps, or IT operations workflows is a strong asset Exposure to red‑teaming or adversarial testing of AI systems Comfortable writing E2E tests with Playwright Familiar with mobile app testing (iOS/Android) We’re building something category‑defining and want teammates who crave ownership, love solving hard problems, and thrive in a high‑bar, high‑impact setting.

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. Unlimited token usage and access to AI tools 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, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. #

📌 Customer Quality Engineer - Software (Toronto)
🏢 Rootly
📍 Toronto