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CheckrCheckrSan Francisco, CA

Senior People Operations and Systems Generalist

Owns Workday business processes, people systems, employee support, reporting, and compliance activities for a scaling People Operations function. Requires deep Workday HCM expertise and 5+ years of People Operations or systems-adjacent experience.

128k – 151k/yr
Hybrid5+ YOEPeople Ops

About the role

Responsibilities

  • Serve as the functional Workday expert for the People Operations team, owning business process design from requirements through configuration, testing, and post-launch iteration.
  • Own configuration, testing, and rollout for semiannual Workday releases, proactively identifying opportunities to simplify or automate processes.
  • Partner with the Workday Product Analyst and internal systems team on larger technical projects and integrations, representing the People Operations perspective.
  • Build lightweight tools using Sheets, trackers, JIRA workflows, Lovable, and Claude to close process gaps and automate workflows.
  • Manage day-to-day Workday data and configuration, including position detail changes, EIB processing, and troubleshooting.
  • Maintain process documentation and create training materials for system enhancements.
  • Provide employee and manager support for complex or system-specific JIRA help desk tickets.
  • Prepare, review, and analyze people data and reports, including attrition and exit interview reporting.
  • Own the immigration vendor relationship and support compliance, multistate policy, and handbook administration.
  • Provide backup support for complex workplace compliance investigations.
  • Support compensation, benefits, equity, and leave administration.
  • Partner on EEO-1 and Affirmative Action Plan reporting.
  • Drive ongoing People Operations process improvements and general team support.

Requirements

  • Deep functional expertise in Workday HCM, including ownership of processes from ideation and requirements through testing and rollout.
  • 5+ years of experience in People Operations or systems-adjacent teams at fast-paced, scaling organizations.
  • Experience partnering with technical systems teams by translating business needs into requirements and testing plans.
  • Familiarity with AI-assisted and no-code/low-code tools such as Lovable and Claude.
  • Expertise with people tools including JIRA Help Desk, Greenhouse, and Culture Amp.
  • Strong customer orientation, collaboration, business acumen, problem-solving, critical thinking, and judgment.
  • Experience handling confidential information with discretion, honesty, and integrity.
  • Strong time management and project management skills, with the ability to manage high request volume and shifting priorities.
  • Working knowledge of Google Workspace, especially Google Sheets, including VLOOKUPs and pivot tables.

Nice-to-Haves

  • Experience with additional Workday modules.

Compensation and Benefits

  • Base salary range: $128,000–$151,000 USD for San Francisco, CA.
  • Competitive cash and equity compensation with advancement opportunities.
  • Learning and development allowance.
  • 100% medical, dental, and vision coverage.
  • Up to $25,000 reimbursement for fertility, adoption, and parental planning services.
  • Flexible paid time off.
  • Monthly wellness stipend.
  • Hybrid in-office arrangement with an expectation of working from the office 3+ days per week.

Skills

workday hcmworkday eibjira help deskGreenhouseculture amplovableClaudeGoogle Sheetsvlookuppivot tablesGoogle Workspace

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