Director - People Systems

About Clear Street 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.

The Role: People Systems Director Clear Street is seeking a People Systems Director to own and evolve our HR technology ecosystem.

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.

, 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.

and

Responsibilities

Workday Implementation Support the full-lifecycle deployment of Workday HCM and Payroll as Clear Street's primary systems implementation owner.

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.

into scalable systems solutions. Maintain documentation of system design decisions, process flows, and configuration specs to build institutional knowledge and support audit readiness.

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. Process Systems Design Approach every configuration decision as a systems architect: consider process integrity, data quality, scalability, and flexibility before building.