Recruiting Systems Lead, Ashby Job at Cypress HCM, San Francisco, CA

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  • Cypress HCM
  • San Francisco, CA

Job Description

We’re looking for a Systems Lead who will serve as a technical partner and Ashby expert—someone who can confidently configure, audit, and train on Ashby and connected recruiting tools, while collaborating with our current system owner to scale best practices and adoption.

You’ll help maintain and optimize recruiting systems, ensure data integrity, and translate technical changes into clear, actionable workflows for the broader team.

This role blends hands-on system administration with enablement and change management, making it ideal for someone who loves solving technical problems while helping people use tools better.

Responsibilities:

System Administration & Governance

  • Partner with the existing Ashby owner to manage system configuration, workflows, automations, and integrations.
  • Independently handle advanced configurations, reporting, permissions, and workflow changes.
  • Support governance enforcement (naming conventions, data entry standards, sourcing attribution, access controls).
  • Coordinate with PMs and system owners on new feature rollouts, user testing, and documentation updates.
  • Contribute to roadmap planning by identifying opportunities for efficiency or automation.

Data Integrity & Compliance

  • Conduct regular data audits across Ashby and connected tools to ensure consistency and completeness.
  • Partner with Analytics to validate reporting fields and data pipelines.
  • Support compliance and privacy efforts (EEO, OFCCP, GDPR), ensuring clean data entry practices.
  • Build and maintain guardrails or dashboards that flag data hygiene issues before they escalate.

Enablement & Training

  • Collaborate with the Enablement PM to design and deliver system training for recruiters and coordinators.
  • Deliver live sessions and create asynchronous materials (Looms, guides, quick references) for system best practices.
  • Identify common system pain points and surface them to Enablement for targeted retraining.
  • Co-own the onboarding experience for new recruiting team members from a systems-access and workflow perspective.

Support & Troubleshooting

  • Act as Tier 2 escalation for Ashby and recruiting system issues.
  • Manage support requests via Slack or Jira, triaging and resolving issues independently when possible.
  • Partner with IT and vendors to troubleshoot complex system or integration issues.
  • Track recurring requests and propose fixes to reduce future manual intervention.

Optimization & Automation

  • Partner with RecOps PMs and system owners to implement, test, and QA automations or optimizations.
  • Translate operational needs into system-side changes or automation logic.
  • Track automation reliability and usage, surfacing patterns or improvements.

Continuous Improvement & Collaboration

  • Stay up-to-date on Ashby product updates, sharing relevant insights with the systems and enablement teams.
  • Proactively recommend process or configuration improvements based on system data and user feedback.
  • Help maintain documentation, change logs, and process maps for all recruiting tools.
  • Act as a collaborative peer to system owners, working in tandem rather than in hierarchy.

Required Qualifications

  • Strong proficiency in Ashby (required) — able to configure, audit, and train others with minimal oversight.
  • Experience as a recruiting systems administrator, operations lead, or enablement partner around Talent & Recruiting Ops in a high-growth environment.
  • Strong understanding of recruiting workflows, data models, and reporting.
  • Excellent communicator who can translate technical changes into accessible, actionable guidance.
  • Highly organized, process-driven, and proactive in identifying and solving problems. Comfortable balancing hands-on execution with cross-functional collaboration.

Success in 6 Months

  • Month 1: Ramp up our recruiting systems and processes, shadow current system owners, and begin supporting day-to-day Ashby administration.
  • Month 2: Conduct a full systems audit across Ashby and connected tools, identifying gaps in governance, data hygiene, and user enablement.
  • Month 3: Launch the first systems training session for recruiters and coordinators, focused on data hygiene, reporting, and workflow best practices.
  • Month 4: Implement key configuration updates and develop scalable training materials for ongoing refresh cycles.
  • Month 5: Partner with the Enablement PM to build repeatable onboarding and retraining modules for systems usage.
  • Month 6: Finalize and hand off a self-sustaining systems training and governance program, complete with documentation, SOPs, and success metrics.

Pay Rate:

  • $100-$115/hour DOE

Location : San Francisco (required, 3 days per week in-office)

Job Tags

Work at office, 3 days per week,

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