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. 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. Responsibilities Workday Implementation 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. Systems Ownership & Roadmap 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. 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 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. 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. Data, Reporting & Governance 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 People Analytics to ensure HR systems serve as a reliable, well-governed data foundation, enforcing data standards, field definitions, and lifecycle management. Administer security controls: manage user roles, access groups, and change management auditing to maintain compliance and audit readiness. Partner with internal and external auditors to ensure effective control design and execution across HR technology. Requirements Experience 15+ years of experience, 7+ years of hands-on experience owning enterprise HR technology platforms, with deep expertise in Workday HCM. Demonstrated experience configuring Workday across multiple modules; ideally HCM, Payroll, Recruiting, Compensation, and 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 that extends beyond HCM: recruiting platforms (e.g., Greenhouse), compensation tooling, and 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 rather than a large team model. Mindset Systems thinker who considers process design, data quality, and downstream impact before making any configuration decision. Builder mentality – energized by the opportunity to design HR technology the right way rather than inherit and maintain what already exists. Strong communicator who can translate technical complexity for non-technical HR partners and senior leaders without losing precision. High bar for documentation, governance, and data quality –leave every system better than you found it. Certifications: Workday HCM Pro certification preferred. Project Management Professional (PMP) or Human Resources Information Professional (HRIP) a plus. We Offer: The Base Salary Range for this role is $220,000-$275,000 This range is representative of the starting base salaries for this role at Clear Street. Where a candidate falls in this range will be based on job related factors such as relevant experience, skills, and location. This range represents Base Salary only, which is just one element of Clear Street's total compensation. The range stated does not include other factors of total compensation such as bonuses or equity. At Clear Street, we offer competitive compensation packages, company equity, 401k matching, gender neutral parental leave, and full medical, dental and vision insurance. Our belief has always been that we are better as a business when we are all together in person. As such, we are requiring employees to be in the office 4 days per week. In-office benefits include lunch stipends, fully stocked kitchens, happy hours, a great location, and amazing views. Our top priority is our people. We’re continuously investing in a culture that promotes collaboration. We help each other through challenges and celebrate each other's successes. We believe that modern workplaces succeed by virtue of having high-performance workforces that are diverse — in ideas, in cultures, and in experiences. We put in the effort to make such a workplace a daily reality and are proud to be an equal opportunity employer. #LIHYBRID