Top Tech Jobs & Startup Jobs in Chicago, IL

Manage regulatory registration and onboarding for FINRA-member broker-dealers and associated persons. Responsibilities include filing Forms BD, BR, U-4, U-5, and NRF; maintaining compliance documentation; coordinating background checks and fingerprinting; supporting continuing education and examinations; reviewing employee disclosures and activities; improving processes; and responding to licensing and registration inquiries.

Leads PeopleX’s AI transformation strategy and roadmap, prioritizes HR use cases, and owns the AI Front Door for People Operations. Designs and deploys AI agents, LLM assistants, automated workflows, and knowledge solutions across Workday, ServiceNow, and related systems. Partners with People Systems and Enterprise Technology to redesign employee lifecycle processes, establish responsible AI controls, measure business impact, and build AI capabilities across HR Operations.

Leads Robinhood’s global BPO partner network and manages Vendor Managers and Performance Analysts. Oversees vendor relationships, operational performance, compliance, reporting, process improvement, cost optimization, commercial contracts, budgets, and service-level agreements. Partners with Product, Finance, Legal, and Compliance to develop network strategy, diversify risk, and improve outsourced customer operations. Requires substantial vendor-management or BPO leadership experience, team-management expertise, analytical skills, and familiarity with Looker, Tableau, or SQL.

Own payroll tax configuration, processing, reporting, reconciliations, filings, and compliance across U.S., Canadian, and international entities. Manage Workday tax setups, resolve historical discrepancies, oversee quarter-end and year-end activities, support audits, handle agency notices, and coordinate with external providers and Finance, Accounting, Tax, Engineering, and People teams.

Own strategic relationships with technology partners, advisor firms, consultants, and other ecosystem stakeholders for TradePMR. Advise RIAs on custody transitions, manage demos and partner resources, lead events and executive engagements, negotiate commercial terms, and equip sales teams with partner collateral. Collaborate with Legal, Compliance, Finance, Marketing, Product, Engineering, and integrations teams to surface partner needs and influence integration priorities. This role is based in Clearwater or Tampa with in-person attendance at least three days weekly.

Oversee programs and launch readiness initiatives across Clearing Operations, coordinating people, processes, and technology. Partner with Product, Engineering, Risk, Compliance, desk leads, and senior stakeholders to ensure operational requirements, regulatory obligations, and efficiency goals are met. Track progress, measure outcomes, communicate updates, and drive multiple medium- to large-scale projects supporting brokerage clearing operations and business growth.

Execute equity and options orders while monitoring live trading across overnight, extended-hours, and regular sessions. Investigate trade inquiries, corporate actions, routing and venue issues, and system disruptions. Follow SEC and FINRA supervisory procedures, coordinate incident responses, and collaborate with Engineering, Product, Compliance, Customer Experience, and external venues to maintain compliant, accurate trading operations.

Leads IT financial compliance and SOX activities, including infrastructure and application control design, IT general controls testing, change management, access governance, data pipeline controls, audit readiness, and remediation. Partners with engineering, security, finance, data, and external auditors to assess systems, document controls, address gaps, and automate evidence collection across cloud infrastructure and financial reporting environments.

Lead valuation analyses for private company investments, minority equity stakes, and other illiquid instruments. Build complex financial models, perform quarterly and event-driven valuations, prepare valuation memos, support financial reporting and SEC disclosures, and partner with auditors, committees, Corporate Development, Legal, and Investor Relations. Maintain SOX controls, improve valuation processes, and advise on complex investment structures and accounting implications.

Design and implement futures risk management programs covering operational and technology risk assessments, automated monitoring and alerting, control testing, regulatory compliance, and risk exposure reporting. Build ETL pipelines, real-time monitoring systems, dashboards, and advanced analytics to identify trading anomalies, system issues, and risk trends. Apply CFTC and NFA requirements to supervisory procedures and controls, investigate complex risk scenarios, and recommend mitigation strategies while partnering with cross-functional stakeholders.