Senior HR AI Tools Evaluator & Knowledge Quality Lead

Obsidian

Toronto

Remote

CAD 90,000 - 120,000

Full time

5 days ago

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Job summary

Obsidian is seeking experienced HR practitioners to evaluate AI-powered HR knowledge tasks. You will assess enterprise search answers for source grounding, permission handling, and content freshness, contributing to quality improvements.

You will judge citations, identify stale content, and distinguish retrieval misses from reasoning errors across multiple AI tools and HR knowledge sources. This is a technology-focused HR evaluation role in Toronto.

Qualifications

5+ years of active HR practice in a specific HR domain.
Currently in an HR/People Ops/Payroll/HR Systems role at a tech company (SaaS/software, internet, hardware, semiconductors).
Regular hands-on use of at least one enterprise search or workplace AI assistant (e.g., Glean, Workday Assistant, Sana, MS 365 Copilot, SharePoint search).
Hands-on experience using Workday HCM as an end user (not just training).
Not primarily a power user or admin of Sana or Glean only.

Responsibilities

Evaluate answers from enterprise search/workplace AI tools on HR topics within your area of expertise.
Judge whether answers are tied to sources and cite them correctly.
Assess whether results respect user access permissions.
Identify stale or conflicting content across knowledge sources.
Distinguish retrieval misses from reasoning errors.