Senior AI Engineer

AI in this role

prompt-engineeringragai-agentsai-research

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:

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?

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.

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, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

How we score this

Senior AI Engineer at Rootly scores 84 out of 100 on AI centrality, which makes it AI Level 4 of 4 (Builds AI) on this board. The level measures how much of the work is AI, not seniority.

Classification

AI Level 4. Building AI systems is the job itself: without AI, the role would not exist.

AI Level 480 to 100
AI Level 360 to 79
AI Level 240 to 59
AI Level 10 to 39

Bands come from how often the tools, models and workflows of the role are named in the posting itself. Open the description and count.

Prepare for this job

A free preview built only from this posting: what it asks for, what you could be asked in an interview, and how to adjust your resume.

Skills and AI tools this role asks for

Prompt EngineeringRagAI AgentsAI Research

Questions you could be asked

How do you structure and test a prompt to get consistent output from a language model?
How would you design a retrieval step so the model answers from real data instead of guessing?
How do you decide when an AI agent can act on its own versus asking for approval first?
Tell me about a research question you investigated. What did you find?
How would you decide a model or AI system is ready to ship?

Adapt your resume

List these exact terms on your resume: Prompt Engineering, Rag, AI Agents, and AI Research. An applicant tracking system matches the wording, not the idea.
Attach one line of real, concrete experience to at least one of them — a tool named with nothing behind it rarely survives a human read.
Lead with what you built, trained or shipped — this role is judged on the AI system itself, not the tools around it.

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