Director - Systems , NY

Clear Street is modernizing the brokerage ecosystem. Founded in 2018, Clear Street is a diversified financial services firm replacing the legacy infrastructure used across capital markets.

We started from scratch by building a completely cloud-native clearing and custody system designed for today’s complex, global market. Clear Street’s proprietary prime brokerage platform adds significant efficiency to the market, while focusing on minimizing risk, redundancy, and cost for clients. Our goal is to create a single source-of-truth platform for every asset class, in every country, and in any currency.

By combining highly skilled product and engineering talent with seasoned finance professionals, we’re building the essentials to compete in today’s fast-paced markets.

Clear Street is seeking a People Systems Director to own and evolve our HR technology ecosystem. Reporting to the HR COO, this role is the technical and strategic owner of how we design, configure, and operate the systems that power our people programs – from recruiting and onboarding through core HCM, payroll, compensation, and workforce planning.

This is not a traditional Workday administrator role. We’re looking for a systems professional who thinks deeply about process design, data architecture, and the downstream implications of every configuration decision. You will be hands‑on – owning configuration, testing, and release management – while also serving as a thought leader who shapes our long‑term HR technology roadmap in partnership with Engineering, Analytics, and the broader People function.

This role sits within the People function, reporting directly to the HR COO alongside People Analytics and HR Operations. As the owner of HR systems, you will be a foundational partner to every function in the People organization.

• Support the full‑lifecycle deployment of Workday HCM and Payroll as Clear Street's primary systems implementation owner.
• Own the functional design across all in‑scope modules, translating requirements from HR, Finance, and business stakeholders into Workday configurations that will scale beyond go‑live.
• Partner with our implementation partner and Engineering to manage integration design, data migration, and environment setup, serving as the authoritative voice on functional decisions throughout.

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

• 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 that ensure every change is production ready.
• Manage feature releases and system updates: evaluate feasibility, assess downstream impacts across the full data and process chain, and communicate changes clearly to stakeholders.
• Execute tenant management, environment refreshes, and EIB/mass data loads as needed.

• Approach every configuration decision as a systems architect: consider process integrity, data quality, scalability, and flexibility before building.
• 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 to build institutional knowledge and support audit readiness.

• Build and maintain foundational reporting and analytics infrastructure within Workday and connected systems, delivering real‑time operational insights to HR and business leaders.
• Partner with…