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Clear StreetClear StreetNew York, NY

Director - People Systems

Own and evolve the HR technology ecosystem as the technical and strategic owner of Workday HCM, Payroll, and integrated platforms. Drive full-lifecycle Workday implementation, configuration, testing, and roadmap development in a lean, high-growth environment.

220k – 275k
On-site15+ YOEPeople Ops

About the role

Responsibilities

Workday Implementation

  • Support the full-lifecycle deployment of Workday HCM and Payroll as the primary systems implementation owner.
  • Own the functional design across all in-scope modules, translating requirements from HR, Finance, and business stakeholders into scalable Workday configurations.
  • Partner with implementation partner and Engineering to manage integration design, data migration, and environment setup.

Systems Ownership & Roadmap

  • Serve as the primary product owner for the full HR technology ecosystem, including Workday HCM, Payroll, recruiting, compensation, onboarding/offboarding, and workforce planning platforms.
  • Develop and maintain the HR Systems roadmap, aligning platform capabilities with business priorities and people strategy.
  • Partner with Engineering on integration architecture and custom development.

Configuration, Testing & Release Management

  • Own configuration of Workday and connected systems: business process design, organizational structures, security frameworks, compensation and benefits setup, and payroll configuration.
  • Lead all testing cycles (unit, regression, and UAT) and define validation procedures.
  • Manage feature releases and system updates; evaluate feasibility, assess downstream impacts, and communicate changes to stakeholders.
  • Execute tenant management, environment refreshes, and EIB/mass data loads.

Process & Systems Design

  • Approach every configuration decision as a systems architect, considering process integrity, data quality, scalability, and flexibility.
  • Partner with HR functional owners in Talent Acquisition, Total Rewards, and People Operations to translate business requirements into scalable systems solutions.
  • Maintain documentation of system design decisions, process flows, and configuration specs.

Data, Reporting & Governance

  • Build and maintain foundational reporting and analytics infrastructure within Workday and connected systems.
  • Partner with People Analytics to ensure HR systems serve as a reliable, well-governed data foundation.
  • Administer security controls: manage user roles, access groups, and change management auditing.
  • Partner with internal and external auditors to ensure effective control design and execution.

Requirements

Experience

  • 15+ years of experience, including 7+ years of hands-on experience owning enterprise HR technology platforms, with deep expertise in Workday HCM.
  • Demonstrated experience configuring Workday across multiple modules (HCM, Payroll, Recruiting, Compensation, Absence/Leave).
  • Strong understanding of data privacy laws, data security, regulatory requirements, and compliance frameworks across multiple regions.
  • Experience operating within a broader HR tech ecosystem extending beyond HCM (recruiting platforms, compensation tooling, workforce planning systems).
  • Proven ability to translate complex, ambiguous business requirements into scalable, well-documented systems solutions.
  • Experience in high-growth or financial services environments preferred.

Technical & Functional

  • Advanced Workday configuration expertise: business process design, security administration, advanced reporting, EIBs, calculated fields, and integrations.
  • Strong command of HR data architecture: how systems connect, where data lives, how changes propagate, and how to maintain integrity across a multi-system environment.
  • Ability to define functional requirements for Engineering-led integration and customization work.
  • Comfortable as a solo system owner in a lean, high-growth environment.

Mindset

  • Systems thinker who considers process design, data quality, and downstream impact before making configuration decisions.
  • Builder mentality – energized by designing HR technology the right way.
  • Strong communicator who can translate technical complexity for non-technical HR partners and senior leaders.
  • High bar for documentation, governance, and data quality.

Certifications

  • Workday HCM Pro certification preferred.
  • Project Management Professional (PMP) or Human Resources Information Professional (HRIP) a plus.

Compensation & Benefits

  • Base Salary Range: $220,000 - $275,000
  • Company equity
  • 401k matching
  • Gender neutral parental leave
  • Full medical, dental, and vision insurance
  • In-office requirement: 4 days per week
  • In-office benefits: lunch stipends, stocked kitchens, happy hours

Skills

Workday HcmWorkday PayrollWorkday ConfigurationBusiness Process DesignSecurity AdministrationEibsAdvanced ReportingCalculated FieldsSystem IntegrationsData ArchitectureHr Data GovernanceGreenhouseCompensation Tooling

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