Principal AI Engineer in Winnipeg

Elastic, the Search AI Company, enables everyone to find the answers they need in real time, using all their data, at scale — unleashing the potential of businesses and people. The Elastic Search AI Platform, used by more than 50% of the Fortune 500, brings together the precision of search and the intelligence of AI to enable everyone to accelerate the results that matter.

What is The Role: The Context Engine team builds the knowledge layer that AI agents use to work with enterprise data in Elasticsearch. We extract knowledge from any data sources into a structured AI Index, serve it to agents through public APIs, MCP tools and framework integrations, and close the loop with agent traces so that what the engine knows improves from real usage. Any agent can use it: Elastic’s own Agent Builder, Claude Code, LangChain and other third‑party harnesses.

As a Principal AI Engineer, you own the improvement loop of this product end to end: how agents, automations and skills behave in production, how we observe them, how we evaluate them, and how we ship changes to them safely. This is a hybrid role at the intersection of engineering, data science, and product. You will write production code, design evaluation and telemetry that product decisions can rest on, and set the technical bar for how the team iterates on agentic behaviour. You will work alongside data scientists, backend engineers, product, and UX, and your work will show up directly in what customers build on top of Elastic.

What You Will Be Doing:

• Own the production improvement loop for Context Engine: understand how extraction automations, retrieval tools and memory behave, based on offline evaluations and customer conversations and telemetry. You help find the failure modes, fix them, and prove the fix.
• Define how we iterate on agents and skills safely: versioning and rollout of prompts, skills and automations, regression coverage, staged and shadow evaluation, and the guardrails that let us change behaviour without breaking customers.
• Design the telemetry we need to make data‑informed engineering decisions: what to capture from agent traces, tool calls and knowledge retrieval, how it lands in Elasticsearch, and how it feeds evaluation, dashboards and the feedback loop.
• Partner with the data science team on evaluation strategy: golden datasets, evaluators to gate on quality, latency and cost.
• Raise the bar across the team: review designs and PRs, mentor engineers in eval‑driven development, and write the technical proposals that shape the roadmap.

What You Bring:

• 10+ years of software engineering experience, with the recent years spent shipping and operating AI‑driven products on real production traffic, ideally products with public APIs and data models that had to evolve without breaking customers.
• A track record of eval‑driven product improvement: you have diagnosed agent or LLM behaviour from traces and user feedback, designed the evaluation that exposed the problem, shipped the fix and measured the outcome.
• Direct experience building agents with state and memory, and iterating on prompts, skills and tool behaviour safely in production.
• Familiarity with MCP, including exposing public MCP servers and tools.
• Experience designing telemetry for AI systems, and using it to make engineering and product decisions.
• Experience running product experiments end to end: instrumentation, unattended execution, and interpreting results.
• Experience building products with public APIs and evolving data models, and the judgement that comes with maintaining external contracts as a product changes.
• Strong backend engineering skills in either Python or TypeScript: APIs, stateful workflows, data pipelines and production services.
• Comfort working with data scientists, engineers, and product managers as peers, translating between measurement and shipping, and communicating trade‑offs clearly.
• A pragmatic, low‑ego style suited to a distributed, async‑first team.

Bonus Points:

• Experience with agent frameworks such as LangGraph, CrewAI, Claude Agent SDK, or similar.
• Agentic retrieval experience, including knowledge representation.
• Practical Elasticsearch experience.

Additional Information - We Take Care of Our People: As a distributed company, diversity drives our identity. Whether you’re looking to launch a new career or grow an existing one, Elastic is the type of company where you can balance great work with great life. Your age is only a number. It doesn’t matter if you’re just out of college or your children are; we need you for what you can do.

We strive to have parity of benefits across regions, and while regulations differ from place to place, we believe taking care of our people is the right thing to do.

• Competitive pay based on the work you do here and not your previous salary
• Health coverage for you and your family in many locations
• Ability to craft your calendar with flexible locations and schedules for many roles
• Generous number of vacation days each year
• Increase your impact - We match up to $2000 (or local currency equivalent) for financial donations and service
• Up to 40 hours each year to use toward volunteer projects you love
• Embracing parenthood with a minimum of 16 weeks of parental leave

Security & Privacy Responsibilities: Take ownership of protecting the confidentiality, integrity, and availability of organizational data and systems by following applicable privacy and security policies, standards, and procedures. Ensure that all individual contributions follow Elastic’s Secure Software Development Framework (SSDF). Proactively participate in mandatory role‑based training to ensure personal technical execution consistently aligns with the highest standards of data protection, data privacy, and system resilience.

Different people approach problems differently. We need that. Elastic is an equal opportunity employer and is committed to creating an inclusive culture that celebrates different perspectives, experiences, and backgrounds. Qualified applicants will receive consideration for employment without regard to race, ethnicity, color, religion, sex, pregnancy, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, disability status, or any other basis protected by federal, state or local law, ordinance or regulation.

We welcome individuals with disabilities and strive to create an accessible and inclusive experience for all individuals.

Compensation for this role is in the form of base salary. This role does not have a variable compensation component. The typical starting salary range for new hires in this role is listed below. These ranges represent the lowest to highest salary we reasonably and in good faith believe we would pay for this role at the time of this posting. We may ultimately pay more or less than the posted range, and the ranges may be modified in the future.

The typical starting salary range for this role is: $154,000—$243,600 CAD