Senior HR Technology Analyst

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk. Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets. We operate with respect, curiosity and open minds. The people who thrive here share our belief that it’s not just what we do that matters–it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus. As a Senior HR Technology Analyst , you will be a hybrid functional and technical subject matter specialist on the HR Technology team—pairing hands-on Workday configuration with strong reporting and analytics skills. You will administer and configure DRW's global HR system, Workday, while also partnering with our HR Reporting Analyst as a responsible owner of scheduled and ad hoc reporting needs across Workday, business intelligence tools, and emerging AI-enabled analytics. You will partner closely with HR and business stakeholders on system support, survey programs, and a variety of business-facing projects that improve employee experience and operational effectiveness. Core Duties: HR Technology & Workday Configuration • Administer and configure Workday HCM across modules such as Core HCM, Payroll, Benefits, Time Tracking, Absence, Compensation, Performance, and Talent, including troubleshooting, processing changes, business process configuration, security maintenance, integration monitoring, EIB creation and loading, and functional testing • Provide senior-level functional support for end users, diagnosing issues, identifying root causes, and delivering durable solutions • Partner with HR stakeholders to gather requirements, translate business needs into Workday configuration, and deliver scalable process improvements that support DRW's growth and employee experience • Support Workday's semi-annual system upgrades, including release note review, design recommendations, configuration, and user acceptance testing • Develop user guides, system documentation, and training materials; assist with Workday training as needed • Maintain HRIS data integrity through audits, analysis, and ongoing data quality practices • Serve as a backup for Workday permissions, security administration, and related system governance • Remain current on HR technology and data strategies, including opportunities to leverage Workday, integrations, BI, and AI tools for operational effectiveness Reporting, Analytics & Insights • Partner with the HR Reporting Analyst as a responsible owner of Workday reporting, calculated fields, dashboards, and related analytics • Own and execute regular scheduled reporting, and support ad hoc reporting requests for HR and business stakeholders • Build, maintain, and improve reports and dashboards in Workday; support reporting needs in adjacent systems (for example, Greenhouse) as needed • Use business intelligence tools and AI-enabled analytics tools to extract, analyze, and present workforce insights that support decision-making • Help maintain the catalog of reports, dashboards, and analytics assets, ensuring accuracy, documentation, and timely delivery • Partner with stakeholders to define reporting requirements, manage expectations, and continuously improve reporting structure and data quality Survey Support & Business-Facing Projects • Support engagement, pulse, and other business survey programs end to end—including setup, administration, reporting, and stakeholder follow-up as needed • Partner with HR and business leaders on survey design, distribution, results packaging, and related action-planning support • Lead or contribute to miscellaneous business-facing HR Technology projects, balancing configuration work, reporting deliverables, and stakeholder communication • Support broader HR Operations and HR Technology initiatives as needed, bringing both systems and analytics perspectives to project work Required Skills & Experience: • Bachelor's degree • 5–7+ years of progressive HRIS / HR Technology experience, with substantial hands-on Workday functional configuration experience in one or more of: HCM, Compensation, Payroll, Benefits, Talent, Time Tracking, Absence Management, Security, and Reporting • Demonstrated Workday configuration and implementation experience, with the ability to translate business needs into technical requirements and deliver production-ready solutions • Strong Workday reporting experience, including designing, building, testing, and maintaining custom reports, calculated fields, and dashboards • Experience owning scheduled reporting cycles and partnering on reporting deliverables in a deadline-driven environment • Proficiency with business intelligence / analytics tools (for example, Tableau, Power BI, or similar); comfort exploring and applying AI tools to accelerate analysis, documentation, and insight generation • Demonstrated ability to use AI tools thoughtfully and effectively for analysis, reporting support, documentation, and problem-solving, with good judgment about when AI adds value and when human review is required • Advanced Microsoft Excel skills, including extracting, manipulating, and validating data to produce accurate, actionable outputs • Experience supporting survey programs (engagement, pulse, or other business surveys) preferred • Strong understanding of HR business processes and operational analysis across areas such as payroll, benefits, compensation, recruiting, tale