Senior AI Engineer

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 out a new multi-billion-dollar category 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, DoorDash, Uber, 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 a 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:

• 5+ years of backend engineering experience: 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.
• $500 stipend for home office setup.
• Unlimited token usage and access to AI tools.
• A fast-moving, high-impact environment where your leadership and ideas directly shape the future of the company.

This is a newly created vacancy.

As we build out the team, we may use AI to support parts of our interview process, like reviewing assessments, but it's a tool that helps our people, not a substitute for their judgement.

If this sounds like the kind of challenge and opportunity you're looking for, apply now and let's build something great together.

Accommodations are available on request at any stage of our recruitment process. Contact recruitment@rootly.com and we will work with you to meet your needs confidentially.

Rootly is an equal opportunity employer. We do not discriminate on the basis of race, ancestry, place of origin, colour, ethnic origin, citizenship, creed, sex, sexual orientation, gender identity, gender expression, age, record of offences, marital status, family status, disability, or any other ground protected by the Ontario Human Rights Code or applicable law.