Search Systems Engineer - Expert - AI Trainer

Obsidian; Chicago (IL); On-site; USD 130,000 - 170,000; Full time

Benefits offered by this job

Paid interview

Job summary

Obsidian is seeking engineers who have shipped production search systems and are deeply thoughtful about search quality and optimization. You should have experience with relevance/retrieval for real users and be able to quantify improvements. We value hands-on experience with agentic search and scalable data infrastructure.

The interview emphasizes practical problem-solving and real-world tradeoffs. This is a 25-minute conversational interview with no coding or take-home tasks; if you stand out,

Qualifications

• Experience shipping production search systems that users rely on.
• Ability to quantify impact and improvements for search systems.
• Experience building systems related to agentic search and scalable data infra.

Responsibilities

• Discuss how you think about search quality, evaluation, and tradeoffs in real systems.
• Bring concrete war stories about search failures and successes.

Skills

Production search systems

Agentic search

Relevance / retrieval

Metrics & evaluation

Job description

We're looking for engineers who have shipped production search systems (especially agentic ones now that we're in the era of LLMs and agents) and are thinking hard about the requirements and optimizations of those systems.

You've probably:

• Owned relevance or retrieval on a system real users depended on

• Decided how to quantify impact and improvements with these systems.

• Built out systems related to agentic search.

• Scaled data infrastructure to power modern search systems.

This is a 25-minute conversational interview. No coding, no take-home. We want to hear how you actually think about search quality, evaluation, and the tradeoffs you've made in real systems. Bring war stories — the messier and more specific, the better.

If your interview stands out, we'll follow up with a paid 30-minute live conversation with our team — $200 for your time, paid on completion of the call.